Title: Legacy Trail Guest Houses from CA $350 | 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)[Vacation Rentals in Legacy Trail](https://expedia.ca/Legacy-Trail-Vacation-Rentals.d553248621532652531.Travel-Guide-VacationRentals)[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) ![Legacy Trail showing a garden](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/553248635975846806/d70ae022-0498-403c-94d8-dc8f29b7750f.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=553248621532652531&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2026-01-30&endDate=2026-02-01&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=553248621532652531&startDate=2026-03-13&endDate=2026-03-15&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Legacy Trail guest houses ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/4ffe13e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/7f7b2ea4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/f28582f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/66000000/65550000/65549500/65549419/w3998h2258x0y0-57eeb69f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Close to Siesta Key beach with a hot tub and a large garden [](https://www.expedia.ca/Sarasota-Hotels-5-Minutes-To-Siesta-And-Cresent-Beaches-In-Sarasota.h65549419.Hotel-Information) Sarasota 9.8/10 Exceptional (114 reviews) "Host was very hospitable and the guesthouse is clean. It was smaller than I imagined, but clean and nice " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carl CA $157 CA $350 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Sarasota-Hotels-5-Minutes-To-Siesta-And-Cresent-Beaches-In-Sarasota.h65549419.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/2550bef6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/735bde6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/c634db4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/91000000/90350000/90345700/90345607/f5a286c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coolest Downtown Neighborhood - Ebikes, Beach Gear, Kayaks, Pickleball [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.Hotel-Information) Central Sarasota 9.8/10 Exceptional (123 reviews) "Great stay! Convenient location, clean, comfortable, and well stocked. Would stay again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristin CA $273 CA $417 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Sarasota-Hotels-Quick-And-Easy-Walk-Downtown-Tons-Of-Amenities.h90345607.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/3267e6a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/3a05ea33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/ed70386e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/93000000/92080000/92071900/92071840/384f8979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Magical Guesthouse 1 mi from SRQ airport [](https://www.expedia.ca/Sarasota-Hotels-Magical-1-Bedroom-Guesthouse-1-Mi-From-SRQ-Airport.h92071840.Hotel-Information) Whitfield Estates 10/10 Exceptional (3 reviews) "This house was absolutely charming! I caught myself In complete awe of every detail - from the fun decor, to the thoughtful inclusion of all kitchen supplies to make a full meal, to the soft shower towels and the incredibly comfortable bed, bedding and pillows! Fantastic stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa D. CA $199 CA $371 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Sarasota-Hotels-Magical-1-Bedroom-Guesthouse-1-Mi-From-SRQ-Airport.h92071840.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/d4dbcc79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/4e18c132.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/bbc3fdb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/72000000/71060000/71059300/71059253/753a219a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta key Guest House 5 star on the water Private [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Guest-House-5-Star-On-The-Water-Private.h71059253.Hotel-Information) South Sarasota 9.0/10 Wonderful (18 reviews) "House was really comfortable, everything worked fine and was cozy. About 15 mins away from Siesta Key Beach..Would def come back. Highly recommend." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giancarlo CA $278 CA $586 total includes taxes & fees Jan 18 - Jan 19 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Guest-House-5-Star-On-The-Water-Private.h71059253.Hotel-Information) ![Beach nearby](https://images.trvl-media.com/lodging/35000000/34110000/34108400/34108344/ffd1ceae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/35000000/34110000/34108400/34108344/c41c7e48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, travel crib, WiFi, bed sheets](https://images.trvl-media.com/lodging/35000000/34110000/34108400/34108344/bcfb0ebf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34110000/34108400/34108344/bba81ab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gulf Front Guest House [](https://www.expedia.ca/Anna-Maria-Hotels-Gulf-Front-Guest-House.h34108344.Hotel-Information) Anna Maria 9.4/10 Exceptional (3 reviews) "The open stairway as you step out of the bathroom seemed hazardous. Perhaps a built-in gate at the top of the stairs would be helpful. Beautiful spot, beach!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia W. CA $486 CA $837 total includes taxes & fees Jan 20 - Jan 21 [](https://www.expedia.ca/Anna-Maria-Hotels-Gulf-Front-Guest-House.h34108344.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=2026-01-31&endDate=2026-02-01®ionId=553248621532652531&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d553248621532652531-aaGuestHouses.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FLegacy-Trail-Guest-Houses.d553248621532652531-aaGuestHouses.Travel-Guide-Accommodation) ## Top Legacy Trail Hotel Reviews ![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "The room was spacious with a large bathroom. Dining tableand living room- all spotless. The staff was friendly and couteous, as well as providing efficient service The beach and pools were fabulous and there were 4 resaurants and two bars to visit and relax. They provided free parking and shuttle into le into St Armand's Circle. We will visit again and would highly recommend it." [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Siesta Key Palms Resort](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda_y.jpg) ### Siesta Key Palms Resort 10/10 Excellent "Everything from the beautiful villa to the staff, gorgeous grounds and the Tikki Bar was exceptional!" [](https://expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information) ![Tropical Breeze Resort](https://images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "All good" [](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "Room was exceptionally clean. Staff was lovely." [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](https://images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "Hotel was nice, rooms clean." [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Cleanliness and friendliness of staff" [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Beautiful facility. Very relaxing. Staff is awesome. Beach is amazing!" [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "Spacious room, good staff, good location close both to the Ringling museum and airport, good parking places, newer building " [](https://expedia.ca/Sarasota-Hotels-Kompose-Boutique-Hotel.h38215316.Hotel-Information) ![Pelican Post at Anna Maria Island Inn](https://images.trvl-media.com/lodging/68000000/67680000/67676100/67676083/4174e2ab_y.jpg) ### Pelican Post at Anna Maria Island Inn 10/10 Excellent "Great room. Very clean. Good communication from property staff. " [](https://expedia.ca/Sarasota-Hotels-Pelican-Post.h67676083.Hotel-Information) ## Find out more about Legacy Trail ## Legacy Trail Guest Houses information | Number of reviews | 248 | | ----------------- | -------------- | | Accommodation | 1 Guest Houses | | Lowest Price | CA $350 | | Highest Price | CA $586 | ## Explore a world of travel with Expedia - Lodging - Packages - More ways to book - [Apartments in Cape Coral ](https://www.expedia.ca/Cape-Coral-Apartments.d6521-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Cape Coral ](https://www.expedia.ca/Cape-Coral-Cabins.d6521-aaCabins.Travel-Guide-Accommodation) - [Chalets in Cape Coral ](https://www.expedia.ca/Cape-Coral-Chalets.d6521-aaChalets.Travel-Guide-Accommodation) - [Cottages in Cape Coral ](https://www.expedia.ca/Cape-Coral-Cottages.d6521-aaCottages.Travel-Guide-Accommodation) - [Country Houses in Cape Coral ](https://www.expedia.ca/Cape-Coral-Country-House.d6521-aaCountryHouse.Travel-Guide-Accommodation) - 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