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.

House Rentals 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 range
    ($188 Average)
    $0per night $1,000+
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...
    Travelers to Longboat Key are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    Sort by
    From
    $145
    / Night
    Payment Protection
    View Details
    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    From
    $1,400
    / Week
    Payment Protection
    View Details
    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Make Inquiry
    From
    $2,250
    / Week
    Payment Protection
    View Details
    1 / 29
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Inquiry
    From
    $335
    / Night
    Payment Protection
    View Details
    1 / 5
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • Parking
    • Towels Provided
    • Private Outdoor...
    • Private Yard
    • Ocean Views
    • Air Conditioning
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Nestled among majestic palms and tropical landscaping, this Country Club Shores home is situated on a deep sailboat water with 113 feet of waterfront, and offers outstanding boating opportunities - all just two houses away from Sarasota Bay! Southern exposure on the canal side provides year-round... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $2,303
    / Week
    View Details
    1 / 24
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • Washer
    • Private Outdoor...
    • Refrigerator
    • Dryer
    • Air Conditioning
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' This beachfront resort is set on beautiful white sand beaches that meet the beautiful turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Rate... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $195
    / Night
    View Details
    1 / 13
    4.5 of 5 stars (21) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Reviews (21) Make Inquiry
    Amenities & Details
    • Internet Access
    • DVD Player
    • Water Views
    • Watersports Nearby
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    July 18-25 and Aug 8-15 are the earliest availability ++++++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
    4 of 5 stars Reviewed June 11, 2015
    Seven of us stayed here...a combination of family and friends. It was great...well-equiped kitchen , extra pillows, large living area, washer & dryer, etc. Location was great...
    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...
    See all reviews
    From
    $400
    / Night
    View Details
    1 / 1
    5 Bedrooms / 4 Bathrooms / Sleeps 12
    Overview Make Inquiry
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our luxury vacation home will comfortably accomodate up to 12 guests and is located on a deepwater canal and has a dock suitable for a boat up to 30 feet in length. Beautiful Longboat Key beach is less than a 10 minute walk from the house and world-class shopping and dining at the famous St.... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $1,750
    / Week
    View Details
    1 / 19
    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • Hot Tub
    • Water Views
    • DVD Player
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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
    5 of 5 stars Reviewed May 28, 2015
    We stayed here from may 9 to 16 with my 2 kids (3.5 and 2 years old), husband and my parents. The house was more than we could ask for. Plenty of room, very nicely decorated...
    See all reviews
    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
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Water Views
    • Waterfront
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    $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
    • DVD Player
    • Internet Access
    • Patio
    • Dishwasher
    • Satellite TV
    • Grill
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    List your property for free!
    List your vacation rental where TripAdvisor travelers can find it.
    Add a Listing
    From
    $125
    / Night
    View Details
    1 / 8
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Patio
    • DVD Player
    • Stereo System
    • Grill
    • Dryer
    • Satellite TV
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    $414
    / Night
    View Details
    1 / 13
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • Waterfront
    • Satellite TV
    • Dryer
    • Private Outdoor...
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    $829
    / Night
    View Details
    1 / 17
    6 Bedrooms / 6 Bathrooms / Sleeps 20
    Overview Make Inquiry
    Amenities & Details
    • Stereo System
    • DVD Player
    • Water Views
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    $300
    / Night
    View Details
    1 / 20
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Waterfront
    • Stereo System
    • Water Views
    • Boat Available
    • Internet Access
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
    $229
    / Night
    View Details
    1 / 22
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • Private Outdoor...
    • DVD Player
    • Stereo System
    • Satellite TV
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    $400
    / Night
    View Details
    1 / 49
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Internet Access
    • Waterfront
    • Private Outdoor...
    • Air Conditioning
    • Stereo System
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located near the historic town of Longboat at the north end of Longboat Key, this Key West-style home is located less than 150 yards from Whitney Beach and the Gulf of Mexico. One of 16 unique homes built by famed architect Frank Folsom Smith, on property formerly owned by the long-time resident,... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228
    From
    $127
    / Night
    View Details
    1 / 5
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Satellite TV
    • Stereo System
    • Dryer
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    House on canal, 5 minute walk to the Beach. A 3bedroom/ 2 bathroom home on the north end of Longboat Key, Florida. One king bed, 2 Queen beds, and One bath has a walk- in shower and the other has the tub choice. A nice large kitchen to cook for your family and friends, while enjoying the space... View all property information
    Make Inquiry
    Location Information
    Longboat Key, Florida 34228