Search Legacy Trail Guest Houses
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Our top choices for Legacy Trail guest houses
Close to Siesta Key beach with a hot tub and a large garden
Close to Siesta Key beach with a hot tub and a large gardenSarasota
9.8 out of 10, Exceptional, (113)
"This place is a must stay we could not fault the place they have thought of everything. Highly recommend this place."
Danny P.
The price is AU$369
includes taxes & fees
27 Dec - 28 Dec
Magical Guesthouse 1 mi from SRQ airport
Magical Guesthouse 1 mi from SRQ airportWhitfield Estates
10.0 out of 10, Exceptional, (3)
"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."
Alyssa D.
The price is AU$396
includes taxes & fees
14 Jan - 15 Jan 2026
Quick and Easy Walk Downtown - Tons of Amenities
Quick and Easy Walk Downtown - Tons of AmenitiesCentral Sarasota
9.8 out of 10, Exceptional, (122)
"Great stay! Convenient location, clean, comfortable, and well stocked. Would stay again!"
Kristin
The price is AU$424
includes taxes & fees
6 Jan - 7 Jan 2026
Siesta key Guest House 5 star on the water Private
Siesta key Guest House 5 star on the water PrivateSouth Sarasota
9.0 out of 10, Wonderful, (18)
"House was really comfortable, everything worked fine and was cozy. About 15 mins away from Siesta Key Beach..Would def come back. Highly recommend."
Giancarlo
The price is AU$703
includes taxes & fees
6 Jan - 7 Jan 2026
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.
Top Legacy Trail Hotel Reviews
Spark by Hilton Sarasota Siesta Key Gateway
10/10 Excellent
Find out more about Legacy Trail
Legacy Trail Guest Houses information
Number of reviews | 246 |
|---|---|
Accommodation | 2 Guest Houses |
Lowest Price | AU$369 |
Highest Price | AU$703 |
Explore a world of travel with Expedia
- Adults Only Hotels in Aloha Kai
- Lgbt Welcoming Hotels in Aloha Kai
- Aloha Kai Hotels
- Bayview Hotels
- Bee Ridge Hotels
- Caravan Parks in Bradenton
- B&B in Casey Key
- Holiday Homes in Casey Key
- Family Hotels in Casey Key
- Ski Hotels in Casey Key
- Casey Key Hotels
- Lodges in Casey Key
- Motels in Casey Key
- Resort in Casey Key
- Fruitville Hotels
- Luxury Hotels in Granada
- Gulf Gate Estates Hotels
- Resort in Island of Venice
- Hotels near Jim Neville Marine Preserve
- Farmstay in Laurel
- Holiday Homes in Laurel
- Holiday Homes in Longboat Key
- Motels in Nokomis
- Holiday Homes in Osprey
- Beach Hotels in Osprey
- Spa Hotels in Osprey
- Osprey Hotels
- Resort in Osprey
- Oyster Bay Hotels
- Palmer Ranch Hotels
- Pinecraft Hotels
- Rivendell Hotels
- Cheap Hotels in San Remo
- Caravan Parks in Sarasota
- Holiday Homes in Sarasota
- Sarasota Hotels
- Luxury Hotels in Sarasota Springs
- Hotels near Siesta Key Beach
- Condo Rentals in Siesta Key
- Cottages in Siesta Key
- Guest Houses in Siesta Key
- Holiday Homes in Siesta Key
- Adults Only Hotels in Siesta Key
- Beach Hotels in Siesta Key
- Casino Hotels in Siesta Key
- Cheap Hotels in Siesta Key
- Family Hotels in Siesta Key
- Luxury Hotels in Siesta Key
- Romantic Hotels in Siesta Key
- Siesta Key Hotels
- Motels in Siesta Key
- Resort in Siesta Key
- Lgbt Welcoming Hotels in Siesta Key Village
- Siesta Key Village Hotels
- Villas in Siesta Key
- South Sarasota Hotels
- Southgate Hotels
- Hotels near Turtle Beach
- Vamo Hotels
- B&B in Venice
- Caravan Parks in Venice
- Guest Houses in Venice
- Holiday Homes in Venice
- Hostels in Venice
- Inns in Venice
- Palaces in Venice
- Pensions in Venice
- Flights to Osprey
- Flights to Sarasota
- Flights to Siesta Key
- Flights from Houston to Siesta Key
- Flights from New York to Siesta Key
- Flights from Orlando to Siesta Key
- Flights from Sydney to Siesta Key
- Flights from Toronto to Siesta Key
- Flights from London to Siesta Key
- Flights from Fort Lauderdale to Siesta Key
- Car hire near Oscar Scherer State Park
- Car hire Sarasota
- Car hire Siesta Key
- Car hire near Southgate
- Car hire near Turtle Beach
- Car hire near Vamo
- Dollar Rent A Car Rental Cars in Siesta Key
- Enterprise Rental Cars in Siesta Key
- Fox Rental Cars Rental Cars in Siesta Key
- Hertz Rental Cars in Siesta Key
- Thrifty Car Rental Rental Cars in Siesta Key