Find hotels in Legacy Trail, FL from $45
Upfront pricingOur total price for your stay includes taxes and fees
Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member Prices
Be pickySearch almost a million properties worldwide
Go beyond your typical stay in Legacy Trail
Pet friendly
Villa
Check prices for these dates
Our top choices for Legacy Trail hotels
1. Tropical Beach Resorts
Tropical Beach ResortsSouth Village
9.4 out of 10, Exceptional, (6,023 reviews)
"Great resort and location!"
Christine
$169 nightly
The price is $191
Nov 29 - Nov 30
Total with taxes and fees
2. Kompose Boutique Hotel
Kompose Boutique HotelSarasota
9.2 out of 10, Wonderful, (6,192 reviews)
"Great room, comfy bed, great location"
Miriam
$87 nightly
The price is $99
Nov 1 - Nov 2
Total with taxes and fees
3. Compass Hotel by Margaritaville Anna Maria Sound
Compass Hotel by Margaritaville Anna Maria SoundBradenton
9.4 out of 10, Exceptional, (2,632 reviews)
"Excellent hotel and amazing staff."
Luddi
$172 nightly
The price is $195
Nov 29 - Nov 30
Total with taxes and fees
4. Siesta Key Palms Resort
Siesta Key Palms ResortSarasota
9.2 out of 10, Wonderful, (1,000 reviews)
"We loved this place, we'll be back."
Melissa
$101 nightly
The price is $114
Nov 29 - Nov 30
Total with taxes and fees
5. Lido Beach Resort
Lido Beach ResortLido Key
9.2 out of 10, Wonderful, (1,000 reviews)
"Awesome place to stay and beach is fabulous"
Bryan
$381 nightly
The price is $431
Nov 30 - Dec 1
Total with taxes and fees
6. Cottages at Siesta Key Inn
Cottages at Siesta Key InnSouth Village
8.8 out of 10, Excellent, (291 reviews)
"Basic no frills place to stay."
Richard
$101 nightly
The price is $114
Nov 29 - Nov 30
Total with taxes and fees
7. Spark by Hilton Sarasota Siesta Key Gateway
Spark by Hilton Sarasota Siesta Key GatewaySarasota
8.2 out of 10, Very good, (2,511 reviews)
"Good location, nice pool and breakfast"
Gaeliel
$109 nightly
The price is $123
Nov 1 - Nov 2
Total with taxes and fees
8. Carlisle Inn
Carlisle InnPinecraft
10.0 out of 10, Exceptional, (2,470 reviews)
"Friendly staff
Great restaurant close by"
Susan
$137 nightly
The price is $155
Nov 30 - Dec 1
Total with taxes and fees
9. Siesta Key Beach Resort and Suites
Siesta Key Beach Resort and SuitesSiesta Key Village
9.2 out of 10, Wonderful, (1,194 reviews)
"Completely enjoyed our stay here. Very clean friendly and helpful staff. Beach is close. Looking forward to coming back."
Nancy
$208 nightly
The price is $235
Nov 1 - Nov 2
Total with taxes and fees
10. Cirque St. Armands Beachside
Cirque St. Armands BeachsideLido Key
9.0 out of 10, Wonderful, (1,003 reviews)
"Great stay"
Christopher
$284 nightly
The price is $321
Nov 1 - Nov 2
Total with taxes and fees
11. Casey Key Resorts - Mainland
Casey Key Resorts - MainlandOsprey
8.6 out of 10, Excellent, (1,252 reviews)
"Clean room, nice staff and great pool area."
Vito
$77 nightly
The price is $87
Nov 29 - Nov 30
Total with taxes and fees
12. Hibiscus Suites - Gateway to Siesta Key
Hibiscus Suites - Gateway to Siesta KeySarasota
8.8 out of 10, Excellent, (2,478 reviews)
"This place was perfect!"
Kat
$138 nightly
The price is $156
Nov 9 - Nov 10
Total with taxes and fees
13. Tropical Breeze Resort
Tropical Breeze ResortSiesta Key Village
8.8 out of 10, Excellent, (1,036 reviews)
"Love the location!"
Samara D.
$128 nightly
The price is $144
Nov 29 - Nov 30
Total with taxes and fees
14. The Residences at Siesta Key Beach by Hyatt Vacation Club
The Residences at Siesta Key Beach by Hyatt Vacation ClubSouth Village
9.6 out of 10, Exceptional, (372 reviews)
"Great location!"
Janell
15. Comfort Suites Sarasota - Siesta Key
Comfort Suites Sarasota - Siesta KeySarasota
9.0 out of 10, Wonderful, (1,802 reviews)
"Nice location nice rooms friendly night staff"
Jymieka
$99 nightly
The price is $112
Nov 1 - Nov 2
Total with taxes and fees
16. The Westin Sarasota
The Westin SarasotaCentral Sarasota
9.2 out of 10, Wonderful, (1,203 reviews)
"Great place"
Mariuxi
$231 nightly
The price is $261
Oct 31 - Nov 1
Total with taxes and fees
17. The Ritz-Carlton, Sarasota
The Ritz-Carlton, SarasotaCentral Sarasota
9.2 out of 10, Wonderful, (1,020 reviews)
"Best hotel I’ve ever stayed at. The staff was amazing. Ready to help at all times! The spa was fantastic, as well as the Beach Club!"
Michael
$652 nightly
The price is $736
Nov 29 - Nov 30
Total with taxes and fees
18. Turtle Beach Resort
Turtle Beach ResortSiesta Key
8.8 out of 10, Excellent, (368 reviews)
"This is a really charming property right on the bay with a small pool and really nice staff. We had a lovely stay. We enjoyed the pool and kayaks with baby dolphins jumping right off the dock 🐬"
Noelle
$274 nightly
The price is $306
Nov 23 - Nov 24
Total with taxes and fees
19. The Capri at Siesta
The Capri at SiestaSouth Village
9.6 out of 10, Exceptional, (847 reviews)
"Lovely location to visit"
Elijah
20. Inn at the Beach
Inn at the BeachVenice Island
9.8 out of 10, Exceptional, (1,109 reviews)
"Everything was amazing very clean great location. Would definitely stay here again."
Jennifer
$175 nightly
The price is $198
Nov 22 - Nov 23
Total with taxes and fees
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.
Learn more about Legacy Trail
Cycle, walk or run the entire length or part of this popular trail. Exit onto junctions to experience a number of environments.
Top Legacy Trail Hotel Reviews
More cheap stays in Legacy Trail
Scottish Inn Jacksonville Downtown
2300 Phillips Hwy Jacksonville FL
$40 nightly
The price is $45 total per night from Nov 1 to Nov 2
$45 total
Nov 1 - Nov 2
Total with taxes and fees
Explore a world of travel with Expedia
- Hotels in North Port
- Lazy River in Siesta Key
- Hotels in Venice
- Hotels in Bradenton
- 2 Star Hotels in Sarasota
- Condos in Siesta Key
- Cottages in Siesta Key
- Hotels in Siesta Key
- 4 Star Hotels in Siesta Key Village
- Best Western Hotels in Sarasota
- Hotels in Sarasota
- Hyatt Hotels in Osprey
- Hotels near Siesta Key Beach
- 2 Star Hotels in Pinecraft
- Red Roof Inn Hotels in Sarasota
- Wyndham Hotels in Siesta Key
- 3 Star Hotels in Osprey
- Spa in Siesta Key
- Pet Friendly Hotels in Palmer Ranch
- Hotels in Osprey
- Hotels in Longboat Key
- Family Friendly in Siesta Key
- Budget in Siesta Key
- Hilton Hotels in Siesta Key Village
- Pool in Osprey
- Romantic in Siesta Key
- Extended Stay America Hotels in Sarasota
- Hotels in Nokomis
- Palmer Ranch Hotels
- 4 Star Hotels in Siesta Key
- Beach in Siesta Key
- 5 Star Hotels in Siesta Key Village
- 5 Star Hotels in Sarasota
- Cabins in Osprey
- All-Inclusive in Siesta Key
- Independent Hotels in Legacy Trail
- Motel 6 Hotels in Sarasota
- Siesta Key Village Hotels
- Ocean View in Siesta Key
- Bee Ridge Hotels
- Hotels near Turtle Beach
- Four Seasons Hotels in Sarasota
- 4 Star Hotels in Sarasota
- Houseboats in Osprey
- Fairmont Hotels in Sarasota
- Hotels near Crescent Beach
- 3 Star Hotels in Siesta Key
- Adults Only in Siesta Key
- Hotels in Osprey Village
- 3 Star Hotels in Venice
- Luxury in Siesta Key
- 2 Star Hotels in Siesta Key
- Marriott Hotels & Resorts Hotels in Siesta Key
- Hotels in Lakewood Ranch
- 5 Star Hotels in Fruitville
- Golf in Siesta Key
- La Quinta Inn & Suites Hotels in Siesta Key Village
- Flights to Siesta Key
- Flights to Osprey
- Delta Air Lines Atlanta (ATL) to Sarasota (SRQ) flights
- JetBlue Airways Boston (BOS) to Sarasota (SRQ) flights
- Flights to Sarasota
- Flights to Nokomis
- Flights from Boston (BOS) to Sarasota (SRQ)
- Flights from Chicago (ORD) to Sarasota (SRQ)
- Flights to Sarasota-Bradenton Intl.
- Flights to Venice
- Enterprise Rental Cars in Osprey
- Van Car Rentals in Sarasota
- Alamo Rent A Car Rental Cars in Legacy Trail
- Luxury Car Rentals in Sarasota
- Car rentals near Gulf Gate Estates
- Car rentals in Sarasota
- Car rentals near Siesta Key Village
- Car rentals near Bee Ridge
- Car rentals in Siesta Key
- ADA Rental Cars in Legacy Trail
- Car rentals in Osprey
