Title: Legacy Trail Vacation Rentals from CA $170: Short-Term Rentals for 2025 | Expedia.ca [Legacy Trail Travel Guide](https://expedia.ca/Legacy-Trail.dx553248621532652531)[Hotels in Legacy Trail](https://expedia.ca/Legacy-Trail-Hotels.d553248621532652531.Travel-Guide-Hotels)[Flights to Legacy Trail](https://expedia.ca/Cheap-Flights-To-Legacy-Trail.d553248621532652531.Travel-Guide-Flights)[Legacy Trail Car Rentals](https://expedia.ca/Car-Rentals-In-Legacy-Trail.d553248621532652531.Car-Rental-Guide)[Legacy Trail Vacation Packages](https://expedia.ca/Legacy-Trail.d553248621532652531.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495922-south-venice.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Legacy Trail Vacation Rentals ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](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 In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Legacy Trail ![Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Bedrooms (Preferred Suite)](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/30b32834.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/28955014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/7dc05471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Beach Resorts Siesta Key 9.4/10 Exceptional (4996) "A great little hotel, the beach is beautiful too, will be back, this is our 3rd year coming." CA $193 CA $249 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Luxury Single | Private kitchenette](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/13f03971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Florida Family Single | Private kitchen](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/06d7bc78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/4d68eb6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captiva Beach Resort Siesta Key 9.0/10 Wonderful (1137) "2nd time and excellent as always..close to the beach and great surroundings " CA $176 CA $223 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information) ![Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/e6cbbbd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/f710e6e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/4b30e45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hibiscus Suites - Gateway to Siesta Key Sarasota 8.6/10 Excellent (2176) "Friendly staff, room was really clean!" CA $156 CA $176 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information) ![Deluxe Suite, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/62be52d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room | Terrace/patio](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/be5906a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/c5bfb01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Room](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/9d53ae34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaSpray Resort Siesta Key 9.4/10 Exceptional (41) "I love everything about this place so beautiful with walking distance to the beach " CA $289 CA $326 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/4174e2ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Room | Living area](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/12fee06e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 Bedroom King Suite | Living area](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/9c445d8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/ce1b2724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pelican Post at Anna Maria Island Inn Bradenton Beach 9.2/10 Wonderful (301) "Place was very clean and perfect location for the beach/surrounding restaurants." CA $236 CA $299 total includes taxes & fees Sep 30 - Oct 1 [](https://www.expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/e9de80f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, open 7:00 AM to 9:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/e9c999e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/ed6dadf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/2c6b16f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ringling Beach House Siesta Key 9.0/10 Wonderful (325) "We liked the stay very much " [](https://www.expedia.ca/Sarasota-Hotels-The-Ringling-Beach-House.h5452904.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/88000000/87370000/87365400/87365320/5a12d0ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/88000000/87370000/87365400/87365320/c2ba7ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/88000000/87370000/87365400/87365320/f9b8957b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, internet, bed sheets](https://images.trvl-media.com/lodging/88000000/87370000/87365400/87365320/be9fb020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times Siesta Key Village 9.8/10 Exceptional (24) "Beatiful property, one block from the beach. Plenty of amenities" [](https://www.expedia.ca/Siesta-Key-Hotels-New-Luxury-Home-With-Private-Pool-And-Waterslide-1-Minute-Walk-To-The-Beach.h87365320.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/a71dc126.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/74884b5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, free WiFi](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/bdd0449e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, pillowtop beds, free WiFi](https://images.trvl-media.com/lodging/17000000/16010000/16001900/16001812/32e3bf8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze at Anna Maria Island Inn Bradenton Beach 9.0/10 Wonderful (38) "Awesome place to stay " CA $307 CA $388 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/Sarasota-Hotels-Anna-Maria-Island-Inn.h16001812.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/7186dbd7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 2 Bedrooms (Royal Palm) | Terrace/patio](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/94684d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 2 Bedrooms (Royal Palm) | Private kitchen](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/a73a11ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Townhome, 2 Bedrooms (Royal Palm)](https://images.trvl-media.com/lodging/2000000/1050000/1045900/1045894/2c5ac217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bridgewalk Resort Bradenton Beach 9.2/10 Wonderful (747) "Great location and staff were knowledgeable about surrounding areas.. " CA $336 CA $380 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Sarasota-Hotels-Bridgewalk-A-Landmark-Resort.h1045894.Hotel-Information) ![On the beach, white sand](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/8623a3bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Economy Studio | Private kitchen](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/75543294.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/81bf853e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio with Balcony | View from room](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/7c582a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Club I Beach Resort Longboat Key 9.2/10 Wonderful (324) "Amazing place, it’s the perfect place for relax and enjoy the beach. I love and I will come back again and again." [](https://www.expedia.ca/Sarasota-Hotels-Sea-Club-I-Beach-Resort.h8109251.Hotel-Information) ![Cabin (Tiny House - The Siesta) | Living area](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/69212d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin (Tiny House Blue Lifeguard Stand)](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/aa6fce22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin (Tiny House - Yellow Lifeguard Stand) | Living area](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/a6eb001c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms (Tiny House - Aqua Oasis)](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/8f76b808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny House Siesta Sarasota 8.4/10 Very good (326) "The location, size and price is just what we needed!" CA $109 CA $202 total includes taxes & fees Sep 25 - Sep 26 [](https://www.expedia.ca/Sarasota-Hotels-Tiny-House-Siesta.h21430911.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/90d49a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms (225 Sea Escape) | Private kitchen](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/c5e64875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom (123 Sea Spray) | In-room dining](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/d400f106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/984b49c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Palms By the Beach Siesta Key 9.2/10 Wonderful (130) "An outstanding experience — a place that leaves you with a strong desire to return." [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Palms-By-The-Beach.h11897601.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/a5a3d5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/6330f667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, free WiFi](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/w5097h3107x0y0-f4bbaa75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch TV with cable channels, MP3 dock](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/2e2e6989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Residences at Siesta Key Beach by Hyatt Vacation Club Siesta Key 9.6/10 Exceptional (290) "We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need. " CA $540 CA $681 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Siesta-Key-Hotels-The-Residences-At-Siesta-Key-Beach-By-Hyatt-Vacation-Club.h3819631.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/78c2df61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/58abfff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/f58c5935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/04923579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kon Tiki Inn Venice 10/10 Exceptional (234) "Love the kon tiki inn. This our second stay. We will be back again. It is close to everything any a great place to stay! " [](https://www.expedia.ca/Venice-Hotels-Kon-Tiki-Inn.h90021825.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/w2398h1348x2y6-214d5e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Private kitchen](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/0104cf78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/2ec0e483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Living area](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/ed4ab08b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bradenton Apartments by Landing Bradenton 7.4/10 Good (45) "Absolutely beautiful location has everything you need n makes you feel like home" [](https://www.expedia.ca/Bradenton-Hotels-Barsala-At-Champions-Walk.h108753056.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/ae9c7c30.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bicycling](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/06c79d70.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Large 2 Bedrooms, 1 Bath, Kitchen, Patio | Private kitchen](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/5c2f5058.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/8000000/7810000/7806300/7806268/1ea9ff08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Venice Beach Villas Venice 9.4/10 Exceptional (442) "I loved staying on the property. The unit was clean and walking distance to shopping, restaurants, a walking trail, and the beach! They also included all amenities you could possibly need!" CA $150 CA $170 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Sarasota-Hotels-Venice-Beach-Villas.h7806268.Hotel-Information) ![On the beach](https://images.trvl-media.com/lodging/118000000/117130000/117124700/117124622/6a763170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/118000000/117130000/117124700/117124622/ba30e550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/118000000/117130000/117124700/117124622/a3ac2151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117130000/117124700/117124622/4332aa53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Private Home Directly on Siesta Key Beach! Siesta Key 9.8/10 Exceptional (6) [](https://www.expedia.ca/Siesta-Key-Hotels-Private-Home-Directly-On-Siesta-Key-Beach.h117124622.Hotel-Information) ![322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/aa15caa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/9ff42f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![153 Beach Rd, Siesta Key, FL W/jacuzzi | Living area](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/fa023698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/08963d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key Island Rentals Siesta Key 9.6/10 Exceptional (48) "This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. " CA $150 CA $374 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Island-Rentals.h89714291.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/72000000/71730000/71728700/71728669/w2047h1364x1y1-d16e7f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/72000000/71730000/71728700/71728669/092080b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/72000000/71730000/71728700/71728669/w2047h1364x1y1-bc3b1b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/72000000/71730000/71728700/71728669/w2047h1364x1y1-4de0bfe3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachfront - New Listing! Anna Maria Island 10/10 Exceptional (26) "We can't say enough good things about this house and the owners! The location, amenities, cleanliness, and communication were all A.We will definitely stay here again!" [](https://www.expedia.ca/Anna-Maria-Hotels-Beachfront-New.h71728669.Hotel-Information) ![Private beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/2000000/1150000/1146400/1146353/6dd9a7bc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1150000/1146400/1146353/5e4ca6e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1150000/1146400/1146353/7eae547b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/2000000/1150000/1146400/1146353/9d2e5693.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tradewinds Beach Resort Bradenton Beach 9.2/10 Wonderful (383) "Very cute place and easy to walk to beach " [](https://www.expedia.ca/Sarasota-Hotels-Tradewinds-Beach-Resort.h1146353.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=2025-10-07&endDate=2025-10-08®ionId=553248621532652531&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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%2FLegacy-Trail-Vacation-Rentals.d553248621532652531.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FLegacy-Trail-Vacation-Rentals.d553248621532652531.Travel-Guide-VacationRentals) ## Top Legacy Trail Hotel Reviews ![Kompose Boutique Hotel](//images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "The staff Julio and Ishak are very welcoming and recommended us great restaurants." [](https://expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](//images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "Great service- nice pool- clean rooms" [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](//images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "Very nice hotel kind people" [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Carlisle Inn](//images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Very clean and nice place. Huge room " [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![Compass Hotel by Margaritaville Anna Maria Sound](//images.trvl-media.com/lodging/42000000/41970000/41961400/41961327/8b0dc5d5_y.jpg) ### Compass Hotel by Margaritaville Anna Maria Sound 10/10 Excellent "The rooms and property was very clean Yhe staff was excellent " [](https://expedia.ca/Sarasota-Hotels-Compass-Hotel-By-Margaritaville.h41961327.Hotel-Information) ![Hyatt Place Sarasota/Bradenton Airport](//images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg) ### Hyatt Place Sarasota/Bradenton Airport 10/10 Excellent "The manager is great! " [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ![Tropical Beach Resorts](//images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Great location, great spot for a vacation. Will be back soon. " [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Art Ovation Hotel, Autograph Collection](//images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/w4000h2662x0y0-652c5c90_y.jpg) ### Art Ovation Hotel, Autograph Collection 10/10 Excellent "Service was excellent" [](https://expedia.ca/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) ![Golden Host Resort - Sarasota](//images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Good price " [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ## Find out more about Legacy Trail **Everything you need to know about** **Legacy Trail** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Legacy Trail vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Legacy Trail vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Legacy Trail. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Legacy Trail vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail vacation rentals we have selected for you start as low as CA $170 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Legacy Trail rentals** At Expedia, we put the best Legacy Trail vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Legacy Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Legacy Trail vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Legacy Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Legacy Trail ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)