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

Longboat Key Cottages

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
loading...
Sort by
From
€118
Per Night
View Details
1 / 7
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (3) Make Enquiry
From
€120
Per Night
View Details
1 / 24
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (6) Make Enquiry
From
€107
Per Night
View Details
1 / 25
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
From
€1,250
Per Week
View Details
1 / 18
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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
Make Enquiry
From
€414
Per Night
View Details
1 / 77
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Gym
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • 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
Make Enquiry
From
€179
Per Night
View Details
1 / 5
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This spectacular two bedroom condominium sits directly fronting on the Gulf in the middle of Long Boat Key. It was recently renovated from floor to ceiling and is beautifully decorated with warm, rich colors. The kitchen has stainless appliances, granite countertops and custom dark polished wood... View all property information
Make Enquiry
From
€169
Per Night
View Details
1 / 17
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • 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
Make Enquiry
From
€3,481
Per Month
View Details
1 / 5
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Directly across the street from the beautiful Gulf of Mexico! Amenities in the unit include Fios internet, 2 flat screened TVs with cable. Windward Bay is a low-density complex offering protected under building parking, extra storage, deeded access to Longboat Key's pristine beach within a short... View all property information
Make Enquiry
From
€98
Per Night
View Details
1 / 29
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Gym
  • Internet Access
  • Satellite TV
  • Sauna
  • Shared Outdoor Pool...
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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
Make Enquiry
From
€166
Per Night
View Details
1 / 26
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautifully decorated one bedroom condo directly on the beach. New kitchen with granite counter tops, and a 47in flat screen TV. Watch the sunset from your living room or porch, the sand is only 20 feet from your front door. View all property information
Make Enquiry
5 of 5 stars Reviewed 2 July 2014
My wife & I just returned from a 4 night stay at this property in Longboat Key and had a wonderful vacation. The condo is beautifully and tastefully decorated, making us feel at...
4 of 5 stars Reviewed 6 May 2014
Stayed there for a week and found it close to perfect. Waking up in the morning and being blessed with dolphins swimming about 10 yards from the beach is bril! If you are...
See all reviews
Get the List
From
€159
Per Night
View Details
1 / 23
1 Bedroom, 1 Bathroom, Sleeps 6
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Beach in/Beach out Condo (Sleeps 6 - in 2 queen beds and 2 more in a queen sofa bed) Rarely will you find spectacular beachfront views AND direct walking access to the magnificent white sand beaches of Longboat Key. This “beach in – beach out” condo is just fifty steps from the Gulf of Mexico!... View all property information
Make Enquiry
1 of 5 stars Reviewed 3 January 2015
The Turtle Crawl Inn, where this condo is housed, has a great location with friendly, professional staff. It is right on the beach and I would recommend the property generally...
4 of 5 stars Reviewed 10 July 2014
My sister and I stayed 3 nights here and wished we had it all week. This location was excellent for our morning walk/run exercise and the beach was beautiful! We saw a sea turtle...
See all reviews
From
€113
Per Night
View Details
1 / 5
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
House on canal, 5 minute walk to the Beach. A 3bedroom/ 2 bathroom home on the north end of Longboat Key, Florida. One king bed, 2 Queen beds, and One bath has a walk- in shower and the other has the tub choice. A nice large kitchen to cook for your family and friends, while enjoying the space... View all property information
Make Enquiry
From
€107
Per Night
View Details
1 / 12
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Absolutely delightful two bedroom, two bath side by side duplex villa, in a great beachside location on North Longboat Key! Relax on the cute front entry screened lanai area, the quiet backyard or take a few minutes to stroll to the beautiful Longboat Key beach. Decorated in 'seaside cottage'... View all property information
Make Enquiry
From
€179
Per Night
View Details
1 / 14
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
**2 WEEK MINIMUM RENTAL** 'Coconut Place' You will love this newly built canalfront pool home on North Longboat Key! This home is an ideal property for a casual Longboat key vacation - - just take a walk to the beach, enjoy a dip in the pool or fishing from the dock. Decorated with a... View all property information
Make Enquiry
From
€147
Per Night
View Details
1 / 10
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
== Up to 25% discount on the regular resort rate == Special rates and discounts are available depending on time and length of stay. Beautiful 3rd floor 2BR/2BR unit #309, overlooking pool, in Sand Cay Beach Resort on the exclusive island of Longboat Key. South facing balcony. Striking views... View all property information
Make Enquiry
From
€4,623
Per Month
View Details
1 / 16
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Magnificent 3 bedroom, 2.5 bath beach front condominium (3 month minimum stay) The Players Club has all the sophistication and stunning scenery that has made Longboat Key a world class destination. This idyllic location is on the south end of Longboat Key just minutes from downtown Sarasota and St.... View all property information
Make Enquiry
From
€319
Per Night
View Details
1 / 49
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Located near the historic town of Longboat at the north end of Longboat Key, this Key West-style home is located less than 150 yards from Whitney Beach and the Gulf of Mexico. One of 16 unique homes built by famed architect Frank Folsom Smith, on property formerly owned by the long-time resident,... View all property information
Make Enquiry
From
€254
Per Night
View Details
1 / 11
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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
Make Enquiry
Enquire for rates
1 / 8
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Lovely completely new fully equipped 3 bedroom beach cottage beautifully decorated with lush landscaping and outdoor lanai for dining and relaxing. Master bedroom, 2 other bedrooms, and 2 full baths plus lanai dining area. Quiet upscale residential neighborhood. Three minute walk to a quiet... View all property information
Make Enquiry
Go to map view
Book Online(54)
Use filters to find the best results!

Suitability

  • Wheelchair access (13)
  • Elder access (50)
  • Suitable for children (11)
  • Pet friendly (7)
  • Smoking allowed (0)

Amenities

  • Air Conditioning (90)
  • Other outdoor space (85)
  • Internet (83)
  • Parking (73)
  • All pools (71)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List
Nearby cities