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Vacation Rentals in Longboat Key, FL

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From
$105
Per Night
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1 / 7
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Studio, 1 Bathroom, Sleeps 2
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$132
Per Night
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1 / 7
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1 Bedroom, 1 Bathroom, Sleeps 4
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$132
Per Night
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1 / 7
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1 Bedroom, 1 Bathroom, Sleeps 4
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$3,795
Per Week
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1 / 25
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Ceiling Fans
  • Guest Count
  • Parking
  • Air Conditioning
  • Shared Outdoor Pool...
  • Internet Access
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This gracious home, with a pool and a private entrance to the beach, offers a lovely location on Longboat Key for all that the area has to offer. There is a nice sense of space with an open living room, kitchen and dining area. There are also two sitting areas that adjoin the bedrooms. The... View all property information
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From
$99
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1 / 18
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Studio, 1 Bathroom, Sleeps 3
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Details Make Inquiry
Amenities & Details
  • TV
  • DVD Player
  • Grill
  • Microwave
  • Washer
  • Patio
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This complex is a two story building with only 15 condos, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. The pictures of the beach and Ocean are taken from the condo, so what you see is what you get, direct beautiful Ocean views. The ground floor studio features a... View all property information
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From
$200
Per Night
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1 / 8
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Details Reviews (1) Make Inquiry
Amenities & Details
  • Microwave
  • Stove
  • Dryer
  • DVD Player
  • Air Conditioning
  • Ceiling Fans
  • Stereo System
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
We have a two bedroom, comfortably furnished condo unit overlooking the Gulf of Mexico. Our favorite room is the lanai - a screened in porch area with dining table and sitting area, especially the views as the sun sets over the Gulf. We are located on the north end of Longboat Key - more secluded... View all property information
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5 of 5 stars Reviewed August 13, 2014
This place is AWESOME, we stayed in the 4 bedroom housebayview with the private pool. It was the perfect vacation. The only mishap was the AC in one of the small rooms stopped...
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From
$1,800
Per Month
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1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Satellite TV
  • # Of Bathrooms
  • Internet Access
  • Ceiling Fans
  • Number Of Bedrooms
  • Patio
  • Shared Outdoor Pool...
  • Guest Count
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a relaxing holiday in this lovely two bedroom, two bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this sought-after resort complex, you'll find all sorts of amenities just outside your door, or across the street on the... View all property information
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From
$120
Per Night
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1 / 25
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Microwave
  • Safe
  • TV
  • Dryer
  • Gym
  • Refrigerator
  • Washer
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
LOCATION, LOCATION, LOCATION! Beautiful view of Sarasota Bay with private beach access just across the street. Newly renovated open kitchen and breakfast bar with seating for three, upgraded stainless appliances, and quartz countertops. Entire unit is freshly painted and immaculate with new tile... View all property information
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From
$1,650
Per Week
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1 / 19
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Hot Tub
  • Washer
  • Dishwasher
  • Refrigerator
  • Stove
  • Parking
  • Dryer
  • Microwave
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
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From
$195
Per Night
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1 / 25
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1 Bedroom, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Gym
  • Balcony
  • Parking
  • Shared Outdoor Pool...
  • # Of Bathrooms
  • Terrace
  • Air Conditioning
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This is a beach lover's paradise. It offers full Gulf of Mexico views from the wall of sliding glass doors in the main living space and the open porch – ideal for relaxing with your morning coffee and throughout the day to your front row seat for the famous west coast sunsets. Recently... View all property information
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From
$4,000
Per Month
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1 / 26
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Terrace
  • Satellite TV
  • Parking
  • Air Conditioning
  • Shared Outdoor Pool...
  • Internet Access
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
You'll enjoy the feel of an old-fashioned Florida beach vacation in this quiet, secluded 8-unit complex nestled on the shores of the Gulf of Mexico at the north end of Longboat Key. This is the definition of the simple life! Australian Pines whisper their invitation to stay and relax for a while.... View all property information
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From
$1,800
Per Month
View Details
1 / 19
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Internet Access
  • Guest Count
  • Grill
  • Ceiling Fans
  • Number Of Bedrooms
  • # Of Bathrooms
  • Parking
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a relaxing holiday in this lovely one bedroom, one bath ground floor unit at popular Whitney Beach, nestled at the north end of Longboat Key. Located on the bay side of this sought-after resort complex, you'll find all sorts of amenities just outside your door, or across the street on the... View all property information
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From
$3,750
Per Month
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1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Internet Access
  • Parking
  • Boat Available
  • Air Conditioning
  • Grill
  • Garage
  • Balcony
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a terrific holiday at Fairway Bay, one of south Longboat Key's most coveted addresses. It's easy to see why people love to stay at this beautiful, sprawling resort. A friendly guard at the gate will welcome you into a lushly landscaped compound, and will direct you down a winding tree-lined... View all property information
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From
$3,000
Per Month
View Details
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Boat Available
  • Parking
  • Internet Access
  • Gym
  • Air Conditioning
  • Ceiling Fans
  • Garage
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Shore is a Gulf-front complex located near the north end of the island, with exquisite views from everywhere on the property. If you treasure your time on the beach relaxing in the sun, you couldn't pick a better spot. Close your eyes and imagine the sound of the wind whispering through the... View all property information
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From
$5,180
Per Month
View Details
1 / 5
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Dishwasher
  • VCR
  • # Of Bathrooms
  • TV
  • Satellite TV
  • Refrigerator
  • DVD Player
  • Private Outdoor...
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Spectacular penthouse condo. Additional amenities include: coffee maker, laundry, ice maker. View all property information
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From
$178
Per Night
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1 / 25
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
Details Make Inquiry
Amenities & Details
  • Terrace
  • Shared Outdoor Pool...
  • Boat Available
  • Air Conditioning
  • Guest Count
  • Parking
  • # Of Bathrooms
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy a vacation filled with extras when you stay at this lovely 3 bedroom, 2 bath Buttonwood Harbour condominium. An attractive complex located at the south end of Longboat Key, Buttonwood Harbour offers a variety of amenities to suit the needs of every vacationer, beginning with a large, heated... View all property information
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From
$192
Per Night
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1 / 27
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Garage
  • Balcony
  • Satellite TV
  • Terrace
  • Shared Outdoor Pool...
  • Ceiling Fans
  • Air Conditioning
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
On beautiful Sarasota Bay in a lush tropical setting, Harbour Bay Club is on Dream Island, only a short walk to the famous beaches of Longboat Key. Comfortably and stylishly decorated, this condo offers stunning views of the Bay from both the living area and the master bedroom. There are two... View all property information
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From
$100
Per Night
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1 / 21
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2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Air Conditioning
  • Number Of Bedrooms
  • Shared Outdoor Pool...
  • Satellite TV
  • Internet Access
  • Terrace
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This second story private mother in law apartment may just be the prettiest waterfront hideaway on Longboat Key. The owners spared no expense when they built this luxury addition to their home, wanting to give their guests the best possible resort experience. With hand-hewn hardwood floors, solid... View all property information
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From
$135
Per Night
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 3
Bookings
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Microwave
  • Washer
  • Refrigerator
  • Safe
  • Parking
  • Stove
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The Beach on Longboat Key - New Gulf Front Condo # 225 This beautiful brand new beach front condo features a modern motif, designer decor, beautifully landscaped, with sophisticated charm and a casual beach atmosphere. A heated pool overlooks the Ocean. The pictures of the beach and Ocean views... View all property information
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From
$2,303
Per Week
View Details
1 / 24
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Dishwasher
  • Stove
  • Microwave
  • Terrace
  • Air Conditioning
  • Dryer
  • Washer
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Beachfront resort, set on beautiful white sand beaches that meet the turquoise waters of the Gulf of Mexico. Resort with golf courses, 6 restaurants, tennis courts, spa, and deep water marina. Studio unit with King bed, sofa sleeper, and full kitchen 'stove top only, no oven' Rate includes resort... View all property information
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From
$110
Per Night
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1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Terrace
  • Parking
  • Grill
  • Gym
  • Air Conditioning
  • Garage
  • Internet Access
  • Balcony
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Will you be the lucky one to take advantage of this VERY RARE OPPORTUNITY to rent for the season at The Player's Club on Longboat Key. This gorgeous complex, featuring four mid-rise buildings facing the Gulf of Mexico, offers only a handful of rentals, most of which have been tenanted by the same... View all property information
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From
$115
Per Night
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1 / 6
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Studio, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • TV
  • Patio
  • Grill
  • Stove
  • DVD Player
  • Dryer
  • Microwave
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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From
$157
Per Night
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1 / 16
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Inquiry
Amenities & Details
  • Dryer
  • Patio
  • Stove
  • Parking
  • Refrigerator
  • Safe
  • Dishwasher
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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
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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...
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From
$171
Per Night
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1 / 29
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Dryer
  • Microwave
  • Stove
  • Parking
  • Grill
  • Dishwasher
  • Refrigerator
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Welcome to your home away from home! Spread out in this beautifully remodeled 3 bedroom top floor unit, soaking in the water views and privacy of the small community of Longboat Landing. Whether you stay for a few nights, weeks, or months, there is plenty to see and do in between long bouts of... View all property information
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5 of 5 stars Reviewed July 13, 2014
We rented this condo on a recent trip to Longboat Key. We chose this unit as we were able to take our boat with us on vacation and dock it at the condo. We utilized a public...
5 of 5 stars Reviewed July 9, 2014
Loved this rental for 7 days. Location has access to the bay, (manatees visited dock), and across the road with access to the beach for swimming was wonderful. Having a 3...
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From
$5,000
Per Month
View Details
1 / 10
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Refrigerator
  • TV
  • Garage
  • Washer
  • DVD Player
  • Parking
  • Microwave
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Spacious and beautiful 2 bedroom beach front property with spectular view of the gulf. Fully furnished with amenities that include pool and tennis courts. Conveniently located within walking minutes of shopping and shops. Within minutes of St. Armand's Circle. Premier location in Longboat... View all property information
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From
$193
Per Night
View Details
1 / 23
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Stove
  • Hot Tub
  • DVD Player
  • Microwave
  • TV
  • Dryer
  • Refrigerator
  • Parking
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
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 lit tennis courts and WiFi access throughout the property. Watch the balcony bathe in the... View all property information
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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...
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From
$179
Per Night
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1 / 14
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Washer
  • Dishwasher
  • Parking
  • DVD Player
  • Microwave
  • Grill
  • Safe
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
ENJOY this beautiful gulf front condominium located in The Cabana Beach Club of charming Longboat Key, just north of Sarasota. Longboat Key is a quiet, lushly landscaped barrier island with no neon or fast food restaurants. It is considered to be one of the Gulf Coast's most beautiful and desirable... View all property information
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5 of 5 stars Reviewed August 28, 2013
Well kept and well located condo in a small comfortable complex. Right on beach and you can enjoy sunsets from your screened in porch. Many nice updates in kitchen, bedroom and...
5 of 5 stars Reviewed January 11, 2013
My family (Mother, husband, 2 teenage children) stayed in unit 118 of this condo for a week. The unit is fabulous, well stocked and right on the beach - gorgeous views all day...
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From
$135
Per Night
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1 / 24
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Stove
  • Satellite TV
  • Parking
  • Refrigerator
  • Dishwasher
  • Washer
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
See my website: www.AwayToParadise.com What's New: As an owner of this condo which I often stay at with my family I always try to improve and make our guests and my family feel as comfortable and pleasant as I can. In Summer 2014 our condo was upgraded with a brand new 55' flat screen Smart... View all property information
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5 of 5 stars Reviewed September 22, 2014
If you think that Florida off-season cannot be enjoyable, think again! We have just spent 2 weeks in September, stayed in #303 and had a fabulous vacation. Below are some...
5 of 5 stars Reviewed August 20, 2014
It was the best vacation in last 20 years! Property location was great, just a few steps away from the beach and nice swimming pool. Unit was very clean, newly renovated...
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From
$167
Per Night
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1 / 41
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Grill
  • Parking
  • Gym
  • TV
  • Safe
  • Microwave
  • Hot Tub
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Available for 3 MONTH MINIMUM rental with approval from condo association. Beautiful beach front condo located just 1.5 miles from St. Armand's Circle. Very upscale and beach feels very private. Pool, spa, and deck newly renovated. We have 24 hour, 7 days a week, guard gated community and... View all property information
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From
$145
Per Night
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1 / 17
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Dishwasher
  • Ceiling Fans
  • Grill
  • Microwave
  • Air Conditioning
  • Refrigerator
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • 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
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From
$200
Per Night
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1 / 6
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 8
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Amenities & Details
  • Stove
  • Patio
  • Washer
  • Refrigerator
  • Dryer
  • Dishwasher
  • Grill
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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From
$177
Per Night
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1 / 6
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Washer
  • Stove
  • Microwave
  • Dryer
  • VCR
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
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
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From
$2,600
Per Month
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1 / 18
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Number Of Bedrooms
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
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$150
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3 Bedrooms, 3 Bathrooms, Sleeps 5
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Amenities & Details
  • Grill
  • TV
  • Patio
  • Dishwasher
  • Refrigerator
  • Microwave
  • Gym
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Secluded, elegant 3 Bedroom, 3.5 Bath condo, almost 3000 sq. ft with 700 sq ft covered wraparound terrace and 3 month minimum rental. Panoramic views of Sarasota bay, golf course, heated pools, hot tub and clubhouse; with workout room, saunas, Har-Tru Tennis courts, BBQ area, children's pool.... View all property information
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5 of 5 stars Reviewed November 21, 2014
This is a beautiful condo with lovely furnishings and every resort amenity one could ask for. Lots of walk in closets, flat screens, Jacuzzi tub, large rooms and great views...
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$83
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Grill
  • Refrigerator
  • Microwave
  • Sauna
  • Dryer
  • Washer
  • DVD Player
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Make this charming Beach Villa your seasonal escape!! 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 nestled between the Gulf Of Mexico and the Bay offers a fully equipped,... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Dishwasher
  • DVD Player
  • Stove
  • TV
  • Ceiling Fans
  • Microwave
  • Satellite TV
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
AwayToParadise com 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... View all property information
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5 of 5 stars Reviewed January 6, 2015
The beach or the pool, it's all steps from the door. The place is well organized, clean, and beautiful. All basic necessities are there. Really enjoyable stay.
5 of 5 stars Reviewed September 18, 2014
My wife and I just came back from our best vacation ever! We have been to a lot of places in our life, but the Longboat Key is our #1 preference, it is heaven on earth! We loved...
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$1,800
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • DVD Player
  • VCR
  • TV
  • Dryer
  • Stove
  • Grill
  • Washer
  • Pool Table
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Looking for a medium/long Stay for 2016 ! MINIMUM : 3 MONTHS My Condo is nicely renovated with 2 beds/2baths in Longboat key! Corner unit, Third floor with elevator Sunny with amazing views! Granite counter in the Kitchen, and the bathrooms Kitchen is well equipped with blenders, Nespresso... View all property information
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$189
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1 Bedroom, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Ceiling Fans
  • Parking
  • TV
  • Microwave
  • Stove
  • Dryer
  • Grill
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
This beautifully appointed spacious 1 BR/1BA is recently renovated and with new furniture, tile flooring, and kitchen upgrades. Enjoy the 180 degree view of the horizon over the beach and the Gulf of Mexico with incredible sunsets. SeaHorse Beach Resort consistently ranks at the top of the... View all property information
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$4,000
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Refrigerator
  • Dishwasher
  • VCR
  • Grill
  • Stove
  • Washer
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful ground floor beachfront 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 , en suite bathroom with two sinks, glass... View all property information
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$195
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1 / 8
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Studio, 1 Bathroom, Sleeps 3
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  • Patio
  • Washer
  • Refrigerator
  • Stove
  • Dryer
  • Dishwasher
  • TV
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Club Suite : Longboat Key Club complex located on the beach , with view of golf course : newly furnished / turn key suite ,fully equipped kitchen ,king bed and sleeper sofa ,new flat screen tv /dvd ,cable ,elevator , a/c, washer /dryer , private lanai deck for entertaining , private parking ,... View all property information
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$142
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2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • DVD Player
  • TV
  • Dryer
  • Refrigerator
  • Patio
  • Microwave
  • Dishwasher
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • 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
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$3,800
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Cute beach bungalow is the perfect compact pool home for those looking for a laid back feel in the quite Longboat Key Village. Just down the street to MarVista, and the Public boat ramp, and a short distance to the beach access this home is made for the water and beach enthusiast. Tastefully... View all property information
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4 of 5 stars Reviewed April 28, 2014
I stayed here with my husband and daughter. The location was great as it is close to the bay and ocean. The neighborhood is quiet with nice neighbors. The peacocks in the...
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$500
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Refrigerator
  • Stove
  • TV
  • DVD Player
  • VCR
  • Dishwasher
  • Safe
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This updated, 2 bedroom and 2 bath condo has sweeping views of the Gulf of Mexico with spectacular sunsets and a quiet beach that stretches for miles. At the north end of Longboat Key, there are plenty of restaurants, shopping and cultural activities nearby. Other amenities include a heated pool,... View all property information
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$1,400
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Washer
  • Grill
  • Patio
  • Microwave
  • Refrigerator
  • TV
  • Garage
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
A lovely pet and family friendly private home, located on a private deep water canal with direct access to Sarasota Bay and only a short walk (200 meters) away from the quiet white sand beach perfect for morning beach-combing and end of day amazing golden sunsets. Located in the prestigious yet... View all property information
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$2,100
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1 / 15
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Patio
  • Dishwasher
  • Garage
  • Stove
  • Parking
  • Microwave
  • Refrigerator
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautifully and completely renovated in 2015, including all new furniture too! This wonderful St. Armand's home is situated on a large corner lot and has been lovingly updated from top to bottom. New bathrooms, new kitchen and appliances, new landscaping. All new furnishings and beautifully... View all property information
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$5,000
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1 / 16
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Parking
  • DVD Player
  • Patio
  • Dryer
  • TV
  • Refrigerator
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
A very warm welcome to your beautiful, home away from home on this Island Paradise! This gorgeous location is truly one of the most relaxing places on the planet, and we know that you are just going to love it! With views of the gorgeous Gulf of Mexico from the living areas, Master Bedroom and... View all property information
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$225
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1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Washer
  • Microwave
  • Patio
  • Dishwasher
  • Stove
  • Grill
  • DVD Player
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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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...
4 of 5 stars Reviewed August 11, 2014
We were pleasantly surprised when we arrived at LaPlaya and entered our unit, which was very clean and nicely decorated. The staff was warm, friendly and very accommodating, too...
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From
$190
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1 / 22
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Refrigerator
  • Stove
  • Stereo System
  • Washer
  • Ceiling Fans
  • Grill
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
SEA PINES This rarely available premier oceanfront location has one of the best views on Longboat Key looking out over the low dunes to the Gulf of Mexico where you can see the dolphins play, and the most amazing sunsets you’ll see anywhere. Quiet and serene with magnificent views, yet only a ten... View all property information
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$129
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1 / 8
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
An oasis by the sea! Ernest Hemingway like red brick walkways lead you to your cottage as well as one of the prettiest beaches in Florida or a serene view of Sarasota Bay. This one bedroom cottage is equipped w/ all of the luxuries not normally seen at a beach place including granite top newly... View all property information
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$148
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1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Terrace
  • TV
  • Air Conditioning
  • Stove
  • Dishwasher
  • Microwave
  • Stereo System
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful 2 bedroom condo for rent by owner on Sand Cay beach. Perfect for families, this vacation rental features flat screen TV's in every room, fine furnishings and everything you need to have an amazing vacation. Please read our reviews, you won't be dissapointed! The condo is unit 208 at the... View all property information
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5 of 5 stars Reviewed May 2, 2014
We three enjoyed four days in late April. Kitchen has every spatula know to mankind, among other tools. Balcony table nicely shaded in the afternoon with sun lounger out in the...
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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.