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Vacation Rentals in Longboat Key, FL

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$110
Per Night
1 / 29
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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$99
Per Night
1 / 18
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Studio, 1 Bathroom, Sleeps 3
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$129
Per Night
1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 3
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$1,214
Per Night
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5 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Dishwasher
  • TV
  • Patio
  • Grill
  • Safe
  • Garage
  • Washer
  • Stove
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
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From
$189
Per Night
1 / 17
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1 Bedroom, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • DVD Player
  • Microwave
  • Refrigerator
  • Dryer
  • Ceiling Fans
  • Dishwasher
  • Stove
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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From
$2,303
Per Week
1 / 24
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1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Dishwasher
  • Stove
  • Microwave
  • Internet Access
  • 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
$4,000
Per Month
1 / 23
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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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From
$464
Per Night
1 / 77
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3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Microwave
  • Dishwasher
  • TV
  • DVD Player
  • Grill
  • Gym
  • Safe
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This luxurious villa on gulf features a heated pool, 3 beautiful terraces, fully-equipped gourmet kitchen & outdoor BBQ grill, fine art & sculpture, high-speed internet, flat screen televisions, video & board games, bicycles, ping pong, & much more. Located near the historic town of Longboat at... View all property information
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From
$3,795
Per Week
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
  • Number Of Bedrooms
  • # Of Bathrooms
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
$132
Per Night
1 / 7
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1 Bedroom, 1 Bathroom, Sleeps 4
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Details Reviews (3) Make Inquiry
Amenities & Details
  • Air Conditioning
  • DVD Player
  • Ceiling Fans
  • Dryer
  • Refrigerator
  • Microwave
  • Satellite TV
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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4 of 5 stars Reviewed September 15, 2014
We have stayed on Longboat Key several times but first time at Las Hermanas. This is a small 4 unit building. We stayed in unit 3. It is a well maintained and updated unit. It...
5 of 5 stars Reviewed August 8, 2014
We wanted to rent a place with an ocean view in a more relaxing (peaceful) place. We arrived to find our rental had a nice updated cottage feel. Plenty of things to do on Longboat...
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From
$105
Per Night
1 / 7
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Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Inquiry
Amenities & Details
  • Patio
  • Washer
  • Refrigerator
  • Ceiling Fans
  • Grill
  • Microwave
  • Dryer
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Longboat Key Bargain on the beach. Our cozy get away on the beach is a favorite of many guests who enjoy the quiet beachfront. Just a simple beach hideaway for your next quiet stay at the beach. View all property information
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5 of 5 stars Reviewed July 24, 2014
So close to the beach, exactly what I was looking for. The studio was cozy and clean, cutely furnished. We loved the outdoor shower and will definitely return again!
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From
$132
Per Night
1 / 7
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Inquiry
Amenities & Details
  • Grill
  • Parking
  • Air Conditioning
  • Ceiling Fans
  • Stove
  • VCR
  • Patio
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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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...
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From
$115
Per Night
1 / 6
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Studio, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Microwave
  • Stove
  • Washer
  • Dryer
  • Grill
  • Ceiling Fans
  • Refrigerator
  • DVD Player
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
$3,500
Per Month
1 / 14
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • DVD Player
  • Dryer
  • TV
  • Stove
  • Pool Table
  • Grill
  • Dishwasher
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Condo renovated 2 beds/2baths in Longboat key third floor..elevator, across from the beach...peaceful, beautiful! tennis, pool, bikes on the island, Publix, CVS, restaurants, shopping, café no pets, no smoking.... Minimum Stay : 1 Month View all property information
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From
$195
Per Night
1 / 8
Payment Protection
Studio, 1 Bathroom, Sleeps 3
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Amenities & Details
  • 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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From
$150
Per Night
1 / 23
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3 Bedrooms, 3 Bathrooms, Sleeps 5
Details Reviews (1) Make Inquiry
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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From
$171
Per Night
1 / 29
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3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Inquiry
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
$165
Per Night
1 / 18
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1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (1) Make Inquiry
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 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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From
$219
Per Night
1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
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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1 / 9
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • DVD Player
  • Balcony
  • Ceiling Fans
  • Parking
  • Sauna
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Behind the gates of the Longboat Key Club, this two-bedroom, two-bath condo has 1400 square feet of living space. The kitchen, living room, dining rooms and baths were completely updated in 2013. The living room has a 42" TV and DVD player. The master bedroom has a king-sized bed, ensuite bath and... View all property information
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5 of 5 stars Reviewed November 30, 2013
This was our second monthly vacation here, after our first visit we knew it was everything we wanted, you are on the beach, the apartment was perfect, the pool the size of an...
5 of 5 stars Reviewed November 6, 2011
My partner and I had the pleasure of renting David and Lucie's apartment for the month of September 2011. Having been to the Sarasota area for the past 20 years we have fallen in...
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From
$145
Per Night
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
$145
Per Night
1 / 13
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Fireplace
  • Parking
  • Dishwasher
  • Ceiling Fans
  • Refrigerator
  • Patio
  • Stove
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • 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. Conde Nast voted Longboat Key the 2nd Best island destination in North American. Just bring your boat, golf clubs, tennis rackets and relax. FREE Wi-Fi & Cable TV Our... View all property information
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From
$3,000
Per Month
1 / 16
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
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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From
$125
Per Night
1 / 19
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Washer
  • DVD Player
  • Hot Tub
  • Microwave
  • Refrigerator
  • Playground
  • Dryer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
DESCRIPTION GULF FRONT-Magnificent views on LONGBOAT KEY Two (2) Bedroom, two (2) Bath Condo with direct and full water views (from Living Room, Dining Room, Kitchen, Master Bedroom and Screened Lanai). Comfortable and beautiful leather sofa in Living Room (opens to a comfortable queen bed). Very... View all property information
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From
$185
Per Night
1 / 30
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Guest Count
  • Number Of Bedrooms
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This luxury, oceanfront end-unit condo is very bright and sunny, with 3 sides of floor to ceiling windows with beautiful water views (Sarasota Bay and Gulf of Mexico) from every room. Longboat Key is a beautiful barrier island that is 11 miles long, located between the counties of Sarasota and... View all property information
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From
$157
Per Night
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
$190
Per Night
1 / 22
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
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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From
$70
Per Night
1 / 25
Payment Protection
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
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 in kitchen and living area. New... View all property information
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From
$225
Per Night
1 / 12
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (13) Make Inquiry
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
$400
Per Night
1 / 1
Payment Protection
5 Bedrooms, 4 Bathrooms, Sleeps 12
Details Make Inquiry
Amenities & Details
  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
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
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From
$143
Per Night
1 / 27
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (1) Make Inquiry
Amenities & Details
  • Washer
  • DVD Player
  • TV
  • Dishwasher
  • Stove
  • Ceiling Fans
  • Refrigerator
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This Gulf Front Condo is tastefully decorated and is completely ready for you to enjoy. The spacious condo features a master suite bedroom and bathroom as well as a guest bedroom and a second full bath. The master bedroom has a king sized bed with top of the line mattress and plenty of... View all property information
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1 of 5 stars Reviewed August 31, 2014
After a long flight from the UK and a 2.5 hour drive from Orlando we were pretty jaded and glad to have finally arrived at our destination, we were informed by the owners that an...
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From
$200
Per Night
1 / 5
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • TV
  • Parking
  • DVD Player
  • Stove
  • Hot Tub
  • Microwave
  • Garage
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
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
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From
$167
Per Night
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
$177
Per Night
1 / 6
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
Details Make Inquiry
Amenities & Details
  • Grill
  • Stove
  • Dryer
  • Refrigerator
  • VCR
  • Stereo System
  • Parking
  • Washer
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
$285
Per Night
1 / 11
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • VCR
  • Stereo System
  • Hot Tub
  • Dryer
  • Washer
  • DVD Player
  • Microwave
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
This deluxe beachfront unit was updated in 2012 with new living room furniture including a 55' flat screen television. Many upgrades fall 2010 include new flooring, kitchen appliances, beautiful kitchen counters and fresh interior paint. The perfect island getaway, located on the southern tip of... View all property information
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From
$89
Per Night
1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Grill
  • Shared Outdoor Pool...
  • Internet Access
  • Guest Count
  • Parking
  • Balcony
  • Air Conditioning
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Lovely 1 bedroom 1 bath rental unit on the second floor. The master bedroom has a king bed and the sofa in the living room is a queen size sleeper sofa. This condo is freshly painted throughout, nicely furnished and has skylights in the ceiling for lots of light. This unit is located close to the... View all property information
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From
$1,375
Per Week
1 / 31
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Pool
  • Parking
  • Air Conditioning
  • Patio
  • Grill
  • Garage
  • Ceiling Fans
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
The beautifully landscaped approach to this charming beach house provides a sense of peace and tranquilty. This is enhanced by the openness of the common rooms which provide ample space for your special vacation. Relax in the entertainment room with the large, flat screen TV. The ground floor... View all property information
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From
$119
Per Night
1 / 22
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Make Inquiry
Amenities & Details
  • Number Of Bedrooms
  • Satellite TV
  • Terrace
  • Balcony
  • Air Conditioning
  • Grill
  • # Of Bathrooms
  • Internet Access
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Enjoy one of the best views of Sarasota Bay in the entire complex from this one bedroom, one bath second floor unit. Completely redecorated with new tile throughout, new furniture, and flat screen LCD TV's in both the living room and the bedroom, this end unit provides a higher degree of privacy... View all property information
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From
$110
Per Night
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Internet Access
  • Fitness Room
  • Balcony
  • Pool
  • Grill
  • Air Conditioning
  • Satellite TV
  • Parking
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
$179
Per Night
1 / 30
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Washer
  • TV
  • Dishwasher
  • Refrigerator
  • Microwave
  • DVD Player
  • Dryer
  • Stove
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
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
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From
$195
Per Night
1 / 25
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Parking
  • Boat Available
  • Pool
  • Internet Access
  • Air Conditioning
  • Grill
  • Fitness Room
  • Balcony
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
$3,000
Per Month
1 / 19
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Garage
  • Internet Access
  • Patio
  • Satellite TV
  • Ceiling Fans
  • Parking
  • Pool
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
$1,800
Per Month
1 / 23
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Internet Access
  • Grill
  • Patio
  • Ceiling Fans
  • Parking
  • Satellite TV
  • Pool
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
$3,750
Per Month
1 / 24
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2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Balcony
  • Parking
  • Boat Available
  • Air Conditioning
  • Pool
  • Garage
  • Fitness Room
  • 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
$159
Per Night
1 / 14
1 Bedroom, 1 Bathroom, Sleeps 3
Details Reviews (6) Make Inquiry
Amenities & Details
  • DVD Player
  • TV
  • Dishwasher
  • Ceiling Fans
  • Washer
  • Microwave
  • Satellite TV
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
For more information on the condo, please see our website at http://www.SEAHORSE247.com 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, not miniature golf and go-cart... View all property information
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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...
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From
$192
Per Night
1 / 27
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Satellite TV
  • Ceiling Fans
  • Balcony
  • Garage
  • Pool
  • Internet Access
  • Fitness Room
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
$142
Per Night
1 / 6
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
Amenities & Details
  • DVD Player
  • Microwave
  • Dryer
  • Parking
  • Patio
  • Refrigerator
  • 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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From
$200
Per Night
1 / 6
Payment Protection
3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
Amenities & Details
  • Stove
  • Patio
  • Washer
  • Parking
  • Dryer
  • Dishwasher
  • Grill
  • Refrigerator
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
$186
Per Night
1 / 18
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
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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From
$357
Per Night
1 / 22
2 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Stereo System
  • DVD Player
  • Refrigerator
  • Dryer
  • Deck
  • Washer
  • Dishwasher
  • Ceiling Fans
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
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  • Wheelchair access (13)
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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.