Title: Longboat Key Cottages from CA $294 | Expedia.ca [Longboat Key Travel Guide](https://expedia.ca/Longboat-Key.dx8409)[Hotels in Longboat Key](https://expedia.ca/Longboat-Key-Hotels.d8409.Travel-Guide-Hotels)[Vacation Rentals in Longboat Key](https://expedia.ca/Longboat-Key-Vacation-Rentals.d8409.Travel-Guide-VacationRentals)[Flights to Longboat Key](https://expedia.ca/Cheap-Flights-To-Longboat-Key.d8409.Travel-Guide-Flights)[Things to do in Longboat Key](https://expedia.ca/Things-To-Do-In-Longboat-Key.d8409.Travel-Guide-Activities)[Longboat Key Car Rentals](https://expedia.ca/Car-Rentals-In-Longboat-Key.d8409.Car-Rental-Guide)[Longboat Key Vacation Packages](https://expedia.ca/Longboat-Key.d8409.Destination-Travel-Guides) ![On the tip of Longboat Key, at the channel that connects the Gulf of Mexico with the Sarasota Bay, there exists a chunk of sandy paradise known colloquially as Beer Can Island. The landscape of this beach is decorated with the remnants of countless fallen Australian Pines (Casuarina). An invasive tree that even after its death lingers. The death of many a chainsaw blade is blamed on its incredibly hard wood. The pure white sand with tree stumps protruding at various angles and entire trees fallen out into the Gulf, makes for a more adventurous beach endeavor.](https://images.trvl-media.com/place/8409/1d0b614f-8c02-41d8-afa7-1b057d73ecfd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by throwingsofas ![](https://images.trvl-media.com/place/8409/1d0b614f-8c02-41d8-afa7-1b057d73ecfd.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=8409&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=8409&startDate=2026-01-30&endDate=2026-02-01&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=8409&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=8409&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Longboat Key cottages ![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/643b1018.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Living area](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/66da17bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Private kitchen](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/cdf5ba63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Living area](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/c6eb17ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Siesta Key [](https://www.expedia.ca/Sarasota-Hotels-The-Inn-On-Siesta-Key.h9768901.Hotel-Information) 10/10 Exceptional (192 reviews) "Great place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carlos CA $219 CA $325 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Sarasota-Hotels-The-Inn-On-Siesta-Key.h9768901.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/121000000/120980000/120979100/120979087/11b164a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/121000000/120980000/120979100/120979087/13a6ee5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120980000/120979100/120979087/ba5110e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120980000/120979100/120979087/b3cc758c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Sarasota [](https://www.expedia.ca/Sarasota-Hotels-Gulf-Gate-Escape-Near-Siesta.h120979087.Hotel-Information) 10/10 Exceptional (1 review) "Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kara F. CA $198 CA $465 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Sarasota-Hotels-Gulf-Gate-Escape-Near-Siesta.h120979087.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/120000000/119220000/119218800/119218723/48baa852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119220000/119218800/119218723/4cdc81ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/120000000/119220000/119218800/119218723/ca750835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119220000/119218800/119218723/68953436.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Bradenton [](https://www.expedia.ca/Bradenton-Hotels-7mi-To-Anna-Maria-Newly-Renovated-Private-Cottage.h119218723.Hotel-Information) 10/10 Exceptional (3 reviews) "I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MO L. CA $99 CA $370 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Bradenton-Hotels-7mi-To-Anna-Maria-Newly-Renovated-Private-Cottage.h119218723.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/9a1e12a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/172e7735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/40337104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83610000/83603900/83603845/7c7c5a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Casey Key [](https://www.expedia.ca/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-B.h83603845.Hotel-Information) 9.2/10 Wonderful (69 reviews) "The Cottage is simple and in need of a few updates, but it is a beach cottage and the salt air is not kind. Overall, the location is fantastic, the Cottage is clean and comfortable and our stay was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bob T. CA $248 CA $624 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-B.h83603845.Hotel-Information) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121760000/121750700/121750643/9a2bb818.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121760000/121750700/121750643/e5f834fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121760000/121750700/121750643/91b3f667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/122000000/121760000/121750700/121750643/4efe0afa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Bradenton [](https://www.expedia.ca/Bradenton-Hotels-3-Mi-To-Downtown-Bradenton-Family-Home-W-Yard.h121750643.Hotel-Information) CA $160 CA $671 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Bradenton-Hotels-3-Mi-To-Downtown-Bradenton-Family-Home-W-Yard.h121750643.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/920c998b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/3b75902b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/7beefd4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/101000000/100770000/100762400/100762365/35e9b7a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Sunny Shores [](https://www.expedia.ca/Bradenton-Hotels-The-Grouper.h100762365.Hotel-Information) 9.4/10 Exceptional (45 reviews) "We really enjoyed our stay here. So close to AMI " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Taylor B. CA $138 CA $294 total includes taxes & fees Feb 7 - Feb 8 [](https://www.expedia.ca/Bradenton-Hotels-The-Grouper.h100762365.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/43000000/42570000/42561000/42560927/dabc6adb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, books, music library](https://images.trvl-media.com/lodging/43000000/42570000/42561000/42560927/e7d7fc92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/43000000/42570000/42561000/42560927/da7614b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/43000000/42570000/42561000/42560927/df1f9aeb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Pass-a-Grille [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Steps-To-Beachbikes-VaCay-Getaway-On-PaG-Island.h42560927.Hotel-Information) 9.8/10 Exceptional (20 reviews) "Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shaunte W. [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Steps-To-Beachbikes-VaCay-Getaway-On-PaG-Island.h42560927.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/124000000/123970000/123961700/123961665/a6c61e98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/124000000/123970000/123961700/123961665/c70c8e0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/124000000/123970000/123961700/123961665/e6ced0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, oven, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/124000000/123970000/123961700/123961665/b9f8f04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Bayou Oaks [](https://www.expedia.ca/Sarasota-Hotels-Cozy-1-Bedroom-Cottage-That-Meetsto-A-County-Park-In-Beautiful-Sarasota-With-AC.h123961665.Hotel-Information) CA $82 CA $149 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Sarasota-Hotels-Cozy-1-Bedroom-Cottage-That-Meetsto-A-County-Park-In-Beautiful-Sarasota-With-AC.h123961665.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/101000000/100410000/100405900/100405851/ddfb4834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/101000000/100410000/100405900/100405851/b40e8265.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/101000000/100410000/100405900/100405851/05f33f79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100410000/100405900/100405851/ef92b92c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Siesta Key [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Sanctuary-Pool-Kayaks-TikiHut-King-Bed.h100405851.Hotel-Information) 9.2/10 Wonderful (5 reviews) "We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rolly N. CA $166 CA $422 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Sanctuary-Pool-Kayaks-TikiHut-King-Bed.h100405851.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35190000/35183800/35183711/5122da99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35190000/35183800/35183711/72c0bdc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/36000000/35190000/35183800/35183711/34efc24b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach towels](https://images.trvl-media.com/lodging/36000000/35190000/35183800/35183711/eae9554a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in South Village [](https://www.expedia.ca/Siesta-Key-Hotels-Heated-Pool.h35183711.Hotel-Information) 9.6/10 Exceptional (81 reviews) "Wonderful experience! It was perfect for a girls’ weekend which included me, my mother & my 12 yr old daughters. There was enough restaurants in walking distance, the beach was in walking distance and we appreciated the trolley and frog hopper to get to Turtle Beach for kayaking. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle A. CA $138 CA $417 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Siesta-Key-Hotels-Heated-Pool.h35183711.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/21000000/20140000/20139300/20139242/d296bf67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20140000/20139300/20139242/1d038a2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/21000000/20140000/20139300/20139242/eaf7ced7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/21000000/20140000/20139300/20139242/89874f88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Sarasota [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Beachside-Getaway-Cottage-Walking-Distance-To-Beach-And-Village.h20139242.Hotel-Information) 9.2/10 Wonderful (177 reviews) "Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alison B. CA $367 CA $657 total includes taxes & fees Jan 19 - Jan 20 [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Beachside-Getaway-Cottage-Walking-Distance-To-Beach-And-Village.h20139242.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/109000000/108550000/108542900/108542882/f63d2f27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/109000000/108550000/108542900/108542882/w1920h764x0y0-c22fef67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108550000/108542900/108542882/e3386d90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/109000000/108550000/108542900/108542882/a41d4a18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Bradenton Beach [](https://www.expedia.ca/Bradenton-Beach-Hotels-Romantic-Island-Getaway-Just-Steps-From-The-Beach.h108542882.Hotel-Information) 8.8/10 Excellent (3 reviews) "It was great! Check in was super easy and anything you would need is nearby. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas N. CA $209 CA $739 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Bradenton-Beach-Hotels-Romantic-Island-Getaway-Just-Steps-From-The-Beach.h108542882.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/51000000/50920000/50919500/50919454/f7169e4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/51000000/50920000/50919500/50919454/dca37942.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/51000000/50920000/50919500/50919454/2d305174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/51000000/50920000/50919500/50919454/8c87680d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Pass-a-Grille [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Townhome.h50919454.Hotel-Information) 9.0/10 Wonderful (18 reviews) "Short walk to the beach and well-kept property. Very neat area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily M. CA $321 CA $537 total includes taxes & fees Feb 2 - Feb 3 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Townhome.h50919454.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/ffc0d99e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/36cab618.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/8cc233be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527715/8d9d80c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Anna Maria [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-With-Covered-Balconies-And-Private-Pool.h73527715.Hotel-Information) 9.6/10 Exceptional (41 reviews) "Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) C. S. CA $326 CA $1,222 total includes taxes & fees Jan 22 - Jan 23 [](https://www.expedia.ca/Anna-Maria-Hotels-Adorable-Cottage-With-Covered-Balconies-And-Private-Pool.h73527715.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/61000000/60620000/60616500/60616412/2c01ef53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/61000000/60620000/60616500/60616412/072a31d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/61000000/60620000/60616500/60616412/f8040a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/61000000/60620000/60616500/60616412/3a85e995.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Siesta Key [](https://www.expedia.ca/Siesta-Key-Hotels-Nook-Cottage-Across-Street-From-Beach-And-Heated-Pool.h60616412.Hotel-Information) 10/10 Exceptional (4 reviews) "They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Derek N. CA $283 CA $759 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Siesta-Key-Hotels-Nook-Cottage-Across-Street-From-Beach-And-Heated-Pool.h60616412.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527703/34769f2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527703/81d3478d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527703/56d1e366.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73530000/73527800/73527703/35ddb29a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Anna Maria [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Condo-On-Pine-Ave.h73527703.Hotel-Information) 8.8/10 Excellent (25 reviews) "Great location, clean, and spacious. Pool didn’t work fir a couple of days but they got it fixed the day before we left " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paris K. CA $491 CA $1,371 total includes taxes & fees Jan 17 - Jan 18 [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Condo-On-Pine-Ave.h73527703.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/8d136d04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/9c941b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/3cde7e09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83610000/83603600/83603529/6b5007b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Casey Key [](https://www.expedia.ca/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-A.h83603529.Hotel-Information) 9.4/10 Exceptional (109 reviews) "A true hidden gem on a great stretch of beach. Loved my time there and would recommend it. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John V. CA $248 CA $590 total includes taxes & fees Jan 13 - Jan 14 [](https://www.expedia.ca/Nokomis-Hotels-Beachfront-Casey-Key-Cottage-A.h83603529.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/326f581a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/01da71cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/411633fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/74000000/73530000/73527600/73527575/3b6db26f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Anna Maria [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Guest-House-Near-The-Beach-With-Private-Pool.h73527575.Hotel-Information) 8.8/10 Excellent (31 reviews) "Beautiful home perfectly located near the beach, bars and restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bibiana G. CA $358 CA $1,188 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/Anna-Maria-Hotels-Beautiful-Guest-House-Near-The-Beach-With-Private-Pool.h73527575.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119720000/119717000/119716938/e977907f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119720000/119717000/119716938/ac814582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/120000000/119720000/119717000/119716938/d78ab203.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books](https://images.trvl-media.com/lodging/120000000/119720000/119717000/119716938/a9349684.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Anna Maria [](https://www.expedia.ca/Anna-Maria-Hotels-SunSalt-Cottage5-Min-To-Beach.h119716938.Hotel-Information) 10/10 Exceptional (1 review) "Absolutely lovely place to stay. The four of us were SO comfortable. The place was clean and beautiful. Very well maintained. You can tell by the high quality finishes that this is someone’s home and they maintain it as such. There was an unforeseen circumstance that popped up with the island doing some work that affected the house while we were there. I messaged the owner and within minutes he had replied and had all the necessary people on the way to fix it. They fixed it all while we were at... ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Devon F. CA $711 CA $1,545 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Anna-Maria-Hotels-SunSalt-Cottage5-Min-To-Beach.h119716938.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980120/8fab23d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980120/ec468328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980120/a91f1f1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/19000000/18990000/18980200/18980120/49ddd283.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage in Pass-a-Grille [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Steps-2-Beach-Island-Cottage-Wking-Bd2bikeparking.h18980120.Hotel-Information) 9.8/10 Exceptional (41 reviews) "Quiet neighborhood away from the tourist areas. 50 steps to a beautiful white sandy beach:) charming little place, very clean and comfortable. sunsets were beautiful and almost no rain all week:)" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James C. CA $277 CA $522 total includes taxes & fees Jan 15 - Jan 16 [](https://www.expedia.ca/St-Petersburg-Clearwater-Hotels-Steps-2-Beach-Island-Cottage-Wking-Bd2bikeparking.h18980120.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-26&endDate=2026-01-27®ionId=8409&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Condos [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=CONDO) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=APARTMENT) Villas [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=COTTAGE) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=CABIN) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=HOUSE_BOAT) Residences [](https://www.expedia.ca/Hotel-Search?destination=Longboat+Key%2C+Florida%2C+United+States+of+America®ionId=8409&latLong=27.412542%2C-82.658989&adults=2&startDate=2026-04-12&d1=2026-04-12&endDate=2026-04-15&d2=2026-04-15&lodging=RESIDENCE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FLongboat-Key-Cottages.d8409-aaCottages.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FLongboat-Key-Cottages.d8409-aaCottages.Travel-Guide-Accommodation) ## Top Longboat Key Hotel Reviews ![Oceanfront Bliss–Longboat Key Beach 106 by RVA](https://images.trvl-media.com/lodging/62000000/61510000/61501000/61500921/4c1f67bf_y.jpg) ### Oceanfront Bliss–Longboat Key Beach 106 by RVA 10/10 Excellent "Beautiful sunset view. " [](https://expedia.ca/Sarasota-Hotels-The-Beach-On-Longboat-Key-106-Studio-1-BA-Resort-By-Rva.h61500921.Hotel-Information) ![Zota Beach Resort](https://images.trvl-media.com/lodging/16000000/15710000/15703500/15703469/277458de_y.jpg) ### Zota Beach Resort 10/10 Excellent "Staff was great" [](https://expedia.ca/Sarasota-Hotels-Zota-Beach-Resort.h15703469.Hotel-Information) ![Oceanfront Oasis – Longboat Key 226 by RVA](https://images.trvl-media.com/lodging/24000000/23140000/23133900/23133871/eb017046_y.jpg) ### Oceanfront Oasis – Longboat Key 226 by RVA 10/10 Excellent "Room was fantastic " [](https://expedia.ca/Sarasota-Hotels-The-Beach-On-Longboat-Key-226-Studio-1-BA-Resort-By-Rva.h23133871.Hotel-Information) ![THE BEACH CONDO #107 BEACHFRONT FULL VIEW](https://images.trvl-media.com/lodging/36000000/35550000/35541700/35541645/9273c908_y.jpg) ### THE BEACH CONDO #107 BEACHFRONT FULL VIEW 10/10 Excellent "Incredible place. Already booked again!! " [](https://expedia.ca/Longboat-Key-Hotels-THE-BEACH.h35541645.Hotel-Information) ![The Resort at Longboat Key Club](https://images.trvl-media.com/lodging/1000000/30000/27600/27542/12e41aae_y.jpg) ### The Resort at Longboat Key Club 10/10 Excellent "Everything Perfect!" [](https://expedia.ca/Sarasota-Hotels-The-Resort-At-Longboat-Key-Club.h27542.Hotel-Information) ![Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views](https://images.trvl-media.com/lodging/39000000/38190000/38188700/38188629/966a6d0f_y.jpg) ### Now Open! 7-Night Deal – Oceanfront w/ Private Balcony & Stunning Views 10/10 Excellent "Nice welcome letter with clear instructions. Great location, beautiful pool, amazing beach, clean grounds and property. Will definitely be back!" [](https://expedia.ca/Longboat-Key-Hotels-AMAZING-OCEAN-VIEWS-FROM-PRIVATE-BALCONY.h38188629.Hotel-Information) ![Country Club Long Boat Key Beach Villa 2B 3BA Pool](https://images.trvl-media.com/lodging/33000000/32670000/32660300/32660283/51ecc90f_y.jpg) ### Country Club Long Boat Key Beach Villa 2B 3BA Pool 10/10 Excellent "The home is in a great location and had all the amenities needed for a week stay. Host responded quickly to our questions and was very responsive to our needs. Several bicycles were available for exercise or quick trips to run errands. " [](https://expedia.ca/Longboat-Key-Hotels-Country-Club-Long-Boat-Key-Beach-Villa-2B-3BA-PoolNo-Hurricane-Damage.h32660283.Hotel-Information) ![The St. Regis Longboat Key Resort](https://images.trvl-media.com/lodging/1000000/10000/5500/5487/1e787841_y.jpg) ### The St. Regis Longboat Key Resort 10/10 Excellent "Everything was new, clean and the service was amazing! The best part is how many activities there are for kids. This is perfect for families to enjoy and relax! We'll be back very soon!" [](https://expedia.ca/Longboat-Key-Hotels-The-St-Regis-Longboat-Key-Resort.h5487.Hotel-Information) ![Sea Club I Beach Resort](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/8623a3bb_y.jpg) ### Sea Club I Beach Resort 10/10 Excellent "Beautiful property " [](https://expedia.ca/Sarasota-Hotels-Sea-Club-I-Beach-Resort.h8109251.Hotel-Information) ## Find out more about Longboat Key ## Longboat Key Cottages information | Number of reviews | 728 | | ----------------- | ----------- | | Accommodation | 23 Cottages | | Lowest Price | CA $294 | | Highest Price | CA $1,545 | ## Frequently asked questions ### Are there any family-friendly cottages in Longboat Key? ### Why book your cottage in Longboat Key with Expedia? ### How can I find cheap cottages in Longboat Key? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Family Hotels in Bay Isles ](https://www.expedia.ca/Bay-Isles-Longboat-Key-Hotels-Family-Hotel.0-n553248635976473218-0-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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