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Vacation Rentals in Longboat Key, FL

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$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
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1 / 7
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1 Bedroom, 1 Bathroom, Sleeps 4
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$140
Per Night
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 3
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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, CONDO # 225 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... View all property information
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From
$115
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1 / 6
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Studio, 1 Bathroom, Sleeps 4
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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
$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
  • 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
$4,000
Per Month
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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
$115
Per Night
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1 / 18
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Studio, 1 Bathroom, Sleeps 3
Booking
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
$195
Per Night
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1 / 8
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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
$171
Per Night
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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
$167
Per Night
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1 / 41
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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
$3,500
Per Month
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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
$189
Per Night
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1 / 17
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1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Inquiry
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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From
$200
Per Night
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1 / 6
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3 Bedrooms, 4 Bathrooms, Sleeps 8
Details Make Inquiry
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
$2,303
Per Week
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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
$177
Per Night
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1 / 6
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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
$150
Per Night
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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
$2,550
Per Month
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1 / 18
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
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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From
$165
Per Night
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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
$185
Per Night
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1 / 30
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
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
$145
Per Night
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1 / 17
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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
$89
Per Night
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1 / 20
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1 Bedroom, 1 Bathroom, Sleeps 4
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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
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1 / 31
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2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Ceiling Fans
  • Shared Outdoor Pool...
  • Garage
  • Parking
  • Number Of Bedrooms
  • Balcony
  • Satellite TV
  • Grill
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
$3,000
Per Month
View Details
1 / 16
Payment Protection
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
$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
$195
Per Night
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1 / 25
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Inquiry
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
$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
  • # Of Bathrooms
  • Number Of Bedrooms
  • 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
$3,000
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
$3,750
Per Month
View Details
1 / 24
Payment Protection
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
$167
Per Night
View Details
1 / 8
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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
$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
$1,800
Per Month
View Details
1 / 23
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Satellite TV
  • Number Of Bedrooms
  • Internet Access
  • Ceiling Fans
  • # Of Bathrooms
  • 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
$178
Per Night
View Details
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
View Details
1 / 27
Payment Protection
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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$285
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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$4,000
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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$100
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2 Bedrooms, 1 Bathroom, Sleeps 4
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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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$145
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • # Of Bathrooms
  • Number Of Bedrooms
  • Guest Count
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  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • 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. Just bring your yacht, golf clubs, tennis rackets and relax. FREE Wi-Fi & Cable TV Our Venetian / Mediterranean Villa is nestled on the placid Longboat Key. With a short... 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
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  • 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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From
$179
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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$125
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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$157
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1 Bedroom, 1 Bathroom, Sleeps 4
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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
$5,000
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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
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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$219
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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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$357
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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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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$110
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Refrigerator
  • Microwave
  • Stove
  • DVD Player
  • Stereo System
  • Dishwasher
  • TV
  • VCR
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
WINDWARD BAY CLUB on beautiful LONGBOAT KEY. This warm and inviting large 2 bedroom 2 bath corner unit is almost paradise. Meticulously furnished with all the comforts of home. Light and bright, with a view of the bay and the Mangroves from the large and roomy lanai. A short walk to the lovely... View all property information
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$190
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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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$70
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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$3,200
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Safe
  • Stove
  • Hot Tub
  • Sauna
  • Garage
  • Microwave
  • Gym
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Directly across the street from the beautiful Gulf of Mexico! Amenities in the unit include Fios internet, 2 flat screened TVs with cable. Windward Bay is a low-density complex offering protected under building parking, extra storage, deeded access to Longboat Key's pristine beach within a short... View all property information
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$223
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Stove
  • Dishwasher
  • VCR
  • Garage
  • Refrigerator
  • Washer
  • Dryer
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Save Over 20% This Christmas. $925 For The Week Reduced From $1,200. January 30% Off, Ranging From $840 - $1,050 Per Week. Bayside on North Longboat Key, this Cedars East townhouse is a great place for a peaceful and relaxing vacation. Guests have access to a beautiful pool and tiki bar in a... View all property information
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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.