We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Apartments and Condos in Longboat Key, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
mm/dd/yyyy mm/dd/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 72 Rentals in Longboat Key
    loading...
    Travelers to Longboat Key are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    Sort by
    From
    $110
    / Night
    View Details
    1 / 10
    5 of 5 stars (13) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (13) Make Inquiry
    From
    $195
    / Night
    Payment Protection
    View Details
    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    From
    $139
    / Night
    View Details
    1 / 28
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    From
    $868
    / Week
    Payment Protection
    View Details
    1 / 6
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Private Fishing...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This is a gulf front studio apartment right on the beach! Sound of the surf will lull you to sleep at night. You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 24, 2015
    Lovely, well appointed, spotlessly clean beach house with tasteful decor and everything to make our stay comfortable and relaxed. Everything tastefully and thoughtfully done...
    See all reviews
    From
    $994
    / Week
    Payment Protection
    View Details
    1 / 7
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Peaceful and quiet spot on the beach. Your one bedroom vacation home has a private beachfront patio and direct gulf views from the patio, lanai, and bedroom. A full kitchen so you can enjoy meals at sunset instead of fighting the crowd at restaurants. Las Hermanas is just one block from our... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed December 10, 2014
    The owners were great, the place safe,clean,equipped,location perfect for walking to dine, shop and enjoy Longboat Key! We will be back!
    5 of 5 stars Reviewed September 28, 2014
    Don't let the word "Motel" detour you from checking out this fantastic property! There are 4 beautiful units right on the beach. Each is complete with full kitchen and there is a...
    See all reviews
    From
    $350
    / Night
    View Details
    1 / 31
    4.5 of 5 stars (11) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (11) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Escape to Paradise with Incredible Sunsets and Balmy Breezes direct on the Gulf of Mexico with its beautiful White Sand Beaches stretching for miles. Private and very quiet, and features two bedrooms with a king size bed in the master suite and a queen size bed in the second bedroom, two full... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed July 3, 2014
    The location and view from the condo was outstanding. The condo came equipped with everything we needed. Easy access to gulf from back porch. Publix was close by to pick up a few...
    See all reviews
    From
    $994
    / Week
    Payment Protection
    View Details
    1 / 7
    5 of 5 stars (5) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    You'll love the quiet and privacy that a small beachfront complex offers. Recently updated interiors all have direct access to the beach and full gulf views . There are only 4 units here in a residential area. One block to the grocery and the trolley stops right in front to take you to St Armands... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed May 19, 2015
    We booked this unit last minute having never been to Longboat Key before. We were looking for peace and relaxation and we found it in this adorable 1 bedroom unit. Clean and fresh...
    5 of 5 stars Reviewed May 2, 2015
    Everything you could want in a vacation rental. We wanted to be right on the beach and this place offers that and more. Great kitchen,stocked with everything you need. Beach...
    See all reviews
    From
    $195
    / Night
    View Details
    1 / 13
    4.5 of 5 stars (20) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (20) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    April 11 is the earliest opening for a rental stay. ++++++Rated ' EXCELLENT' digital badge on TripAdvisor and FlipKey++++++. This exclusive award recognizes outstanding vacation rentals based on reviews of past year so you can rent with confidence.... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed February 26, 2015
    Our two families of 8 people total enjoyed our stay at Castle in the sky very much. The house is large but very comfortable. The weather in January can be fickle so one day the...
    2 of 5 stars Reviewed January 14, 2015
    Although it is actually bizarre to book an expensive double house for only 2 ladies we did so, because we wanted to treat ourselves when we saw the photo on the VRBO website of a...
    See all reviews
    From
    $175
    / Night
    Payment Protection
    View Details
    1 / 8
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Charming 1 bedroom 1 bath canal front unit. On canal with dock in the Back yard. A beautiful Beach, amazing 35 acre park, great restaurants All within a five minute walk. Great space in an amazing place! Everything you Need to relax for a long weekend, a week, a month, or a winter, or summer... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $910
    / Week
    Payment Protection
    View Details
    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Hot Tub
    • Internet Access
    • Safe
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Directly across the street from the beautiful Gulf of Mexico! Amenities in the unit include Fios internet, 2 flat screened TVs with cable. Windward Bay is a low-density complex offering protected under building parking, extra storage, deeded access to Longboat Key's pristine beach within a short... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $2,250
    / Week
    Payment Protection
    View Details
    1 / 29
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    About this property
    Nestled among majestic palms and tropical landscaping, this Country Club Shores home also available VRBO #704978 is situated on a deep sailboat water canal with 113 feet of waterfront, and offers outstanding boating opportunities - all just two blocks away from Sarasota Bay! Southern exposure on... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $125
    / Night
    Payment Protection
    View Details
    1 / 5
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Inquiry
    Amenities & Details
    • Grill
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    One bedroom one bath cottage all new beds, Linens, towels etc. Cottage available weekly or monthly in the Lovely North Longboat Key Village where resident peacocks visit daily. Sit out on your porch in the evening and relax or dine out at many of the water front restaurants. Offered FULLY... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $87
    / Night
    View Details
    1 / 25
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Sauna
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    * CONDE NAST VOTED LONGBOAT KEY THE SECOND BEST ISLAND DESTINATION IN NORTH AMERICA * Located on fabulous Longboat Key approximately 3 miles south of Anna Maria island, 6 miles north of Armand's Circle at Windward Bay.This 27 acre condominium complex situated between the Gulf Of Mexico and the Bay... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $225
    / Night
    View Details
    1 / 12
    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (14) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    La Playa is a small 21-unit resort property of privately-owned condominiums available exclusively for weekly rentals twelve-months per year. Located on spectacular Longboat Key, a short drive from Sarasota on the wide sand beaches of the Gulf of Mexico, La Playa offers privacy and direct beach... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 23, 2015
    We have been coming down to Longboat Key from Chicago for several years now, staying at "our" unit at La Playa. Every year is always a great experience. The best part is simply...
    5 of 5 stars Reviewed December 14, 2014
    La Playa is a little gem, situated in the centre of beautiful Longboat Key. There is a beautiful private beach, and all the amenities needed for a perfect Gulfshore holiday...
    See all reviews
    From
    $850
    / Week
    Payment Protection
    View Details
    1 / 29
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    One bedroom one bath very affordable cottages are available weekly or monthly in the eclectic Longbeach Village where resident peacocks visit daily. New Beds, Linens, Towels etc.. Also available on VRBO #706230 Offered FULLY FURNISHED with each unit reflecting its own style of a beach getaway... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $140
    / Night
    Payment Protection
    View Details
    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Housekeeping...
    • Housekeeping...
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Up to 4 person private accommodation in our deluxe studio Unit 222 with a beautiful Gulf view completely renovated, remodeled and refurbished in September 2014. With new furniture and stainless steel appliances. Face the sunset over the Mexican Gulf that you could enjoy every evening, having a cup... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $125
    / Night
    View Details
    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Lovely completely new fully equipped 3 bedroom beach cottage beautifully decorated with lush landscaping and outdoor lanai for dining and relaxing. Master bedroom, 2 other bedrooms, and 2 full baths plus lanai dining area. Quiet upscale residential neighborhood. Two minute walk to a quiet clean... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $120
    / Night
    Payment Protection
    View Details
    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Internet Access
    • Washer
    • Waterfront
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This quiet 1 bedroom cozy stone cottage is nestled on the North end of Exclusive Longboat key. Sister Island to Anna Maria Island. A natural wild life preserve. Peacocks roam the streets, Sea turtles nest, Dolphins frolic and parrots fly freely, in this tropical paradise. Shopping, sight seeing... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $99
    / Night
    Payment Protection
    View Details
    1 / 18
    Studio / 1 Bathroom / Sleeps 3
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The Beach on Longboat Key - New Gulf Front Condo # 103 *** Beach Front Special ~ From $99/night or 1 night FREE *** May 26 to June 4 , June 7 to June 11 , June 16 to June 19 This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $2,240
    / Month
    View Details
    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Longboat Key 2 Bedroom 2 Bath Condominium at Seaplace (2 month minimum stay) This newly remodeled and updated, 2 bedroom 2 bath, open living area condominium is tastefully decorated and in immaculate condition. A two month minimum stay is required. Luxury vacation rental properties like Seaplace... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    Get the List
    From
    $1,400
    / Week
    Payment Protection
    View Details
    1 / 6
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Million Dollar unobstructed ocean views. Right on the beach. Top floor. About a mile north from St Armand Circle. The condo has 2 bedrooms and 2 baths. Kitchen has granite and the place has everything you need. Just bring your clothes and food. Beautiful patio to enjoy the sunset views. Wi-Fi... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $602
    / Week
    Payment Protection
    View Details
    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Condo is located in Banyan Bay Club which consists of a total of only 44 units arranged in two floors. This condo is located at the Garden level. No stairs. The lanai at the rear of the unit opens onto a private Banyan and Palm tree-filled lawn with views of Sarasota Bay. The lanai contains a table... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $132
    / Night
    View Details
    1 / 21
    3.5 of 5 stars (2) Average
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Pet friendly, Unique Bungalow Canal Home on the North End of Longboat Key. Unique Bungalow Canal Home on the North End of Longboat Key. If you have been putting off writing the next great American novel due to the lack of a peaceful setting then this quaint canal home may be just the place for you.... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed March 18, 2014
    The cottage was well reflected by the pictures. Everything fairly new and clean. Beds comfortable, has everything. Area quiet but short drive to Bradenton and Holmes beaches, for...
    See all reviews
    From
    $189
    / Night
    View Details
    1 / 26
    5 of 5 stars (4) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door. View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 33312
    5 of 5 stars Reviewed July 2, 2014
    My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at...
    4 of 5 stars Reviewed May 6, 2014
    Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
    See all reviews
    From
    $179
    / Night
    View Details
    1 / 30
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Ocean Views
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    Our condo has everything you will need for a relaxing vacation on the beach. The island of Longboat Key... ... is one of the most beautiful places in Florida. Longboat was voted the second most favored island in North America, according to a survey by a nationally recognized travel magazine.... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 4725
    From
    $145
    / Night
    Payment Protection
    View Details
    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Internet Access
    • Ocean Views
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Doctor's hidden home with gorgeous views: walk to Florida's best secluded beaches. Longboat Key is a tropical paradise. Just bring your yacht, golf clubs, tennis rackets and relax. Wi-Fi & Cable TV Our Venetian / Mediterranean Villa is nestled on the placid Longboat Key. With a short drive... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $414
    / Night
    View Details
    1 / 13
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    **ONE WEEK MINIMUM RENTAL HOME** This casual beach home is just the right place to enjoy a laid-back, toes-in-the-sand vacation! Nestled on the shores of the Gulf of Mexico at the north end of Longboat Key, it's the perfect spot for relaxing days on the beach, followed by fabulous sunsets and... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $3,640
    / Month
    View Details
    1 / 20
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Gym
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Spacious corner unit 2 bedrooms 2.5 bathrooms (3 month minimum stay) The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic luxury beach location is on the south end of Longboat Key just minutes from downtown Sarasota and... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $193
    / Night
    Payment Protection
    View Details
    1 / 23
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    !!!!SUMMER SPECIAL!!!! JULY & AUGUST 2015 - ONLY 1,000 USD/WEEK OR 1,750 USD FOR 2 WEEKS Feel at home in this spacious waterfront condominium on Longboat Key with luxurious amenities, including heated pool and hot tub with views of the Sarasota Bay, tropical gardens, private boat dock and four... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 9, 2015
    All 'first" for us. First time on Longboat Key, first time at spring training and first time using Tripadvisor/Flipkey. And the property - first rate : ). The location was great...
    5 of 5 stars Reviewed October 15, 2014
    The condo was spotless and well equipped with all of our vacation needs. The rooms are spacious and the view is stunning. We will never stay anywhere else when we go to Florida...
    See all reviews
    From
    $5,180
    / Month
    View Details
    1 / 16
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Magnificent 3 bedroom, 2.5 bath beach front condominium (3 month minimum stay) The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic location is on the south end of Longboat Key just minutes from downtown Sarasota and St.... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $829
    / Night
    View Details
    1 / 17
    6 Bedrooms / 6 Bathrooms / Sleeps 20
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Looking for tropical seclusion on a private island? Georgous sunsets with blue, blue waters? If so, then look no further. Nestled among the lush vegetation, your private polynesian beach house awaits your arrival! Accessible only by boat,this getaway assures you complete privacy and relaxation.... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $159
    / Night
    View Details
    1 / 14
    5 of 5 stars (6) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (6) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    NATURAL BEAUTY of Longboat Key RIGHT ON THE BEACH PANORAMIC 2ND FLOOR BALCONY VIEWS On beautiful tropically landscaped Longboat Key, Florida you will find the natural beauty. Our Studio condo is right on the beach with magnificent panoramic views from its second floor balcony position. ENJOY THE... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed August 9, 2014
    Everything was perfect for 2 people. Nice decor, room set-up and proximity to beach. Quiet, mostly private feel (except for renovations being done next door). easy to arrange the...
    5 of 5 stars Reviewed July 21, 2014
    My husband and I enjoyed everything about our stay in this beautiful condo. Not only did we have a nicely decorated room inside, but our view was amazing outside. We were able to...
    See all reviews
    From
    $151
    / Night
    View Details
    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    == Up to 25% discount on the regular resort rate == Special rates and discounts are available depending on time and length of stay. Beautiful 3rd floor 2BR/2BR unit #309, overlooking pool, in Sand Cay Beach Resort on the exclusive island of Longboat Key. South facing balcony. Striking views... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $250
    / Night
    Payment Protection
    View Details
    1 / 6
    3 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    The Outrigger Resort is a quaint 10 unit complex. This unit is equipted with very comfortable furniture and all your needed appliances and accessories. Included in the kitchen is stove, refrigerator, toaster, coffee pot, etc., including all necessary utensils. The unit is designed with front... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $1,225
    / Week
    Payment Protection
    View Details
    1 / 21
    4.5 of 5 stars (3) Very good
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    This one-bedroom, ground floor walk-out, has fantastic full gulf views and is only steps to the beach. It features a bright beach decor that will make your vacation in paradise truly memorable. The screened lanai is practically perched upon the sand! An added bonus is that it is a corner unit... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed November 27, 2014
    Very clean appartment, well equipped kitchen for self catering, with all the kitchen utensils spotlessly clean, very good position on the beach. Quite and very peaceful. Would go...
    5 of 5 stars Reviewed June 13, 2014
    I am reluctant to review the property because it might be more difficult to get the weeks I want! My husband and I first went to this place 35 years ago when friends recommended...
    See all reviews
    From
    $1,750
    / Week
    View Details
    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Large Gated Home on waterway - White Sand Beach only steps away. Our vacation home is spacious and beautifully furnished with 3 bedrooms and a large loft with sleeper-sofa, 3 full bathrooms, sleeps uo to 8 people, Perfect for families or couples. The home has a fully equipped gourmet kitchen with... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $169
    / Night
    View Details
    1 / 20
    4 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Safe
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Our gulf front condominium has a beautiful view of the Gulf of Mexico not only from the balcony, but from the living room as well. We also have two other condos in this same resort that rent at lesser rates than shown below. We only recently purchased this condo, but in 2013 we replaced all the... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed May 19, 2015
    I was celebrating my 30th wedding anniversary. I could not of picked a better place. The rental was super clean had everything you can imagine there for use. I will definitely...
    5 of 5 stars Reviewed October 23, 2014
    This place was very clean and updated. The extra amenities such as the cooler's and ice packs was a huge plus. We had plenty of bedding, and towels and bathroom stuff. It’s not a...
    See all reviews
    From
    $300
    / Night
    View Details
    1 / 20
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Set on a 30 acre private island a few hundred yards off North Longboat Key, this new water front home (completed in 2012) will provide an island vacation experience for you and your family like no other. The house has 2 bedrooms, an outside sleeping porch/bunk bed, along with 2 1/2 bathrooms and an... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $176
    / Night
    View Details
    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    The perfect island getaway, located on the southern tip of Longboat Key with a beautiful beach and pool area. This deluxe unit features approximately 1700 square feet with a 52’ long, open beachfront lanai. The views cannot be beat! The beach is great and the pool and hot tub inviting too! The... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $229
    / Night
    View Details
    1 / 22
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Save 15% this May and June. $3400 for the month reduced from $4000. $1360 per week reduced from $1600 The Banyan home is ideally located just four blocks to the beach on the south end of Longboat Key in Country Club Shores. Situated on a large corner lot this spacious home has all new... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $167
    / Night
    View Details
    1 / 39
    5 of 5 stars (5) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    At our beautiful low-rise resort, located directly on the beach, our two-bedroom condominium is fifty paces from the pool and a private beach of soft white sand. 15F in popular Casa del Mar provides a spacious living room/home theatre (46 inch plasma TV & BlueRay Player), vaulted ceilings, and a... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed March 19, 2015
    Casa Del Mar is located in a beautiful part of Long Boat Key. The beach is beautiful and F15 condo was only steps away from the beach. There were plenty of lounge chairs on the...
    5 of 5 stars Reviewed July 4, 2014
    This is the first time we stayed at this property, and it was amazing !!! It was everything we were told it would be. Our unit had updated appliances, a TV in every room, a brand...
    See all reviews
    From
    $178
    / Night
    View Details
    1 / 23
    3.5 of 5 stars (3) Average
    1 Bedroom / 1 Bathroom / Sleeps 6
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beach in/Beach out Condo (Sleeps 6 - in 2 queen beds and 2 more in a queen sofa bed) Rarely will you find spectacular beachfront views AND direct walking access to the magnificent white sand beaches of Longboat Key. This “beach in – beach out” condo is just fifty steps from the Gulf of Mexico!... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    1 of 5 stars Reviewed January 3, 2015
    The Turtle Crawl Inn, where this condo is housed, has a great location with friendly, professional staff. It is right on the beach and I would recommend the property generally...
    4 of 5 stars Reviewed July 9, 2014
    My sister and I stayed 3 nights here and wished we had it all week. This location was excellent for our morning walk/run exercise and the beach was beautiful! We saw a sea turtle...
    See all reviews
    From
    $200
    / Night
    Payment Protection
    View Details
    1 / 5
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    This spectacular two bedroom condominium sits directly fronting on the Gulf in the middle of Long Boat Key. It was recently renovated from floor to ceiling and is beautifully decorated with warm, rich colors. The kitchen has stainless appliances, granite countertops and custom dark polished wood... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $58
    / Night
    View Details
    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    ***Minimum 30 Day Rental*** Longboat key offers uncrowded beaches, great food and serene accommodations. Bayport Beach and Tennis Club is a beach to bay complex made up of 2 story buildings that offer privacy in a very serene and relaxing environment. 843 Bayport way is a 2 bedroom 2 bath upper... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $1,000
    / Night
    View Details
    1 / 44
    4 of 5 stars (1) Very good
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This spacious 5 bedroom villa is situated directly on the beautiful white sand beaches of Longboat Key. Offering a large outdoor private heated swimming pool and glorious views of the Gulf of Mexico from almost every corner, fully-equipped gourmet kitchen, fireplace, BBQ, and much more - it is your... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    4 of 5 stars Reviewed April 27, 2015
    I have had my eye on this house for 2 years now. Boy am I glad that I finally pulled the trigger and decided to stay here. Traveled with my wife, two children ages 2&4 and...
    See all reviews
    From
    $142
    / Night
    Payment Protection
    View Details
    1 / 13
    2 Bedrooms / 1 Bathroom / Sleeps 4
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Welcome to Longboat Key! This 2 bedroom one bath ground floor condo offers a full kitchen, with open living and dining area. There is a enclosed patio opening to the community pool. Covert Condominiums are located on the northern part of Long Boat Key on Sarasota Bay. There is deeded beach access... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $214
    / Night
    Payment Protection
    View Details
    1 / 6
    1 Bedroom / 1 Bathroom / Sleeps 4
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Beautifully furnished 1 bedroom/1 bath condo overlooking the Gulf of Mexico. Stroll for miles on the white sandy beaches of Beautiful Longboat Key or just relax and enjoy the sunsets View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $1,850
    / Month
    Payment Protection
    View Details
    1 / 21
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Ping Pong Table
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    • Welcoming, distinctive, fully furnished 2 bedroom, 2 bathroom condo in a verdant, tropical environment. • Very private and quiet first floor, 1600 ft. unit with lush garden views. • Master suite with office niche, king size bed, walk-in closet and double sinks in bathroom. • Guest bedroom with... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $3,500
    / Month
    Payment Protection
    View Details
    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Beautiful ground floor beachfront (on Gulf of Mexico) 3 bedroom, 2 full bath condo on Longboat Key. Fully furnished kitchen, washer and dryer (in unit), dedicated parking for 1 car directly in front of unit, with additional guest parking. Master Bedroom has a king sized bed, flat screen TV, en... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $137
    / Night
    View Details
    1 / 52
    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (8) Make Inquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Safe
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    B00KED UNTIL 7/31. AUG - OCT DEAL - $4000/45 Nights 8/1-10/29 FOR MINIMUM BOOKINGS & RATES SCROLL DOWN TO BOTTOM OF THIS SECTION PACK YOUR SWIMSUIT & SMILE - THE REST IS HERE: Take the wooden walkway to swim in warm gentle azure gulf waters Walk softly past sea turtle nests & shell on... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    5 of 5 stars Reviewed April 14, 2015
    The two balconies and lanai overlooking the fabulous Gulf of Mexico provide a beautiful and ever-changing view of Nature's best work. Condo is large, clean and comfortably...
    5 of 5 stars Reviewed November 29, 2014
    Club Longboat is a wonderful development with excellent property managers. I stayed at Ed's condo from August thru October of 2014. Even during the 'low season', this area is just...
    See all reviews
    Beachfront condos and bayside villas – your vacation rental on Longboat Key

    Imagine overlooking Sarasota Bay and relaxing in your own villa pool garden … or enjoying crimson sunsets from your Gulf front family vacation condo. Beach and bay rental homes deliver the best of all worlds with spacious living, exceptional kitchens and easy access to Longboat Key parks, shopping and upscale or relaxed dining selections. For fishing excursions or family vacations, select rentals offer flexibility and value for holidays at the beach.

    Longboat Key - the upscale coastal vacation destination

    This gorgeous Florida key combines serene seashore enjoyment with luxury shopping and dining choices. Families enjoy the many water sport activities from fishing, boating and kayaking to plucking perfect seashells along the shoreline. Couples and friends explore chic dining and shopping spots around St. Armand’s Circle. The aristocratic heritage of the St. Armand and Ringling families resonates through quiet gardens and plush Palm Beach-style shopping. Umbrella-draped cafes and handsome restaurants offer exceptional European fare and inventive coastal specialties. Work off that decadent dessert with a stroll around the circle for leather, jewelry, resort wear and art gallery browsing.

    Cultural treasures along Sarasota Bay

    Venture just across the bridge over Sarasota Bay for unrivalled cultural treats. The Ringling circus family bequeathed an elegant legacy of art and architecture. The estate includes the acclaimed John and Mable Ringling Museum of Art, the family’s winter Ca’ d’Zan mansion – a Venetian Gothic masterpiece - the Circus Museum and historic Asolo Repertory Theater. With elegant gardens and terraces spread over 20 bayside acres, the complex provides hours of enjoyment.

    Waterfront dining

    Beyond the eclectic mix of St. Armand Circle restaurants, you’ll want to sample excellent bay front restaurants. The Dry Dock is a favorite of locals and visitors alike, with waterside dining under coconut palms or indoor seating with the same exceptional views. Boasting ultra fresh grouper sandwiches, char-grilled burgers and a host of pasta and chicken selections, the Dry Dock grill is a casual dining treat. Diners arrive by car or boat to enjoy Mar Vista Dockside Restaurant and Pub in the historic village at the North end of the key. With quaint indoor or outdoor dining and spectacular views, try steamer pots of fresh seafood or exotic scallop and crab dishes that wash down quite well with islander mojitos, margaritas and other such flavorful concoctions. Land lovers can choose from the number of chicken, steak and pork dishes.

    Visitor reviews aid vacation rental selection

    You’ll have no trouble knowing what to expect, as you search for the just-right villa or condo rental. Our unbiased visitor reviews offer clear descriptions and candid evaluations, so you can feel confident in your choice.