Legacy Trail Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
9 Aug - 10 Aug
Tomorrow
10 Aug - 11 Aug
Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug

Holiday Rentals in Legacy Trail

Tropical Beach Resorts
Relax by the serene pool surrounded by lush tropical vegetation and lounge under the shade of a blue umbrella.

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4849)
"Very Nice Resort!"
The price is HK$1,094
HK$1,414 total
includes taxes & fees
1 Sept - 2 Sept
Tropical Beach Resorts
SeaSpray Resort
Living area

SeaSpray Resort

4.0 star property
9.2 out of 10, Wonderful, (9)
"Nice place to stay in SK! "
The price is HK$1,641
HK$1,854 total
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort
Hibiscus Suites - Gateway to Siesta Key
Relax by the pool surrounded by palm trees and a soothing waterfall.

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2158)
"Bed comfort , great location, friendly staff. "
Hibiscus Suites - Gateway to Siesta Key
Pelican Post at Anna Maria Island Inn
Stunning building with a distinctive roof and lush tropical surroundings.

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (288)
"This was an amazing property and we can’t wait to come back on our next trip to the island."
The price is HK$1,441
HK$1,823 total
includes taxes & fees
1 Sept - 2 Sept
Pelican Post at Anna Maria Island Inn
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
Relax by the serene pool surrounded by lush greenery and palm trees, set amidst a tranquil atmosphere.

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

10.0 out of 10, Exceptional, (22)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times
The Ringling Beach House
Classic hotel with a symmetrical facade, central entrance, and upper-level balcony.

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (317)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House
Tiny House Siesta
Relax in a cozy seating area with a sofa and flat-screen TV, plus a staircase to an upper level.

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (305)
"It was a good experience. Good location. "
The price is HK$628
HK$1,153 total
includes taxes & fees
10 Aug - 11 Aug
Tiny House Siesta
Captiva Beach Resort
Relax in the Captiva chair, surrounded by lush greenery and a stylish sign.

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
Captiva Beach Resort
Bridgewalk Resort
Outdoor pool, pool umbrellas, pool loungers

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (733)
"We loved the remodeling and location. We only stayed one night but the room was amazing with enough space for a family four. Can't wait to stay again."
The price is HK$2,098
HK$2,371 total
includes taxes & fees
9 Sept - 10 Sept
Bridgewalk Resort
Seabreeze at Anna Maria Island Inn
Enjoy ocean views from this deck with tables and chairs under umbrellas, surrounded by a railing.

Seabreeze at Anna Maria Island Inn

3.0 star property
8.8 out of 10, Excellent, (25)
"Great location"
The price is HK$1,936
HK$2,450 total
includes taxes & fees
1 Sept - 2 Sept
Seabreeze at Anna Maria Island Inn
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (275)
"Fun place to stay for family vacation "
The price is HK$3,703
HK$4,584 total
includes taxes & fees
25 Aug - 26 Aug
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sea Club I Beach Resort
Relax in style with comfortable lounge chairs overlooking the ocean.

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (318)
"Nice place "
Sea Club I Beach Resort
Kon Tiki Inn
Relax in a serene outdoor space surrounded by palm trees and a low wall, featuring a central pathway and decorative door.

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (218)
"One of my fave places ever!"
The price is HK$1,093
HK$1,235 total
includes taxes & fees
11 Aug - 12 Aug
Kon Tiki Inn
Siesta Key Island Rentals
Enjoy cooking in this kitchen with a refrigerator, oven, and dishwasher, and a convenient green tiled backsplash.

Siesta Key Island Rentals

3.0 star property
9.4 out of 10, Exceptional, (43)
"Quiet neighborhood, clean and well maintained property, responsive management."
Siesta Key Island Rentals
Swivel On Anchor
Relax in comfort with a plush sofa and enjoy scenic views through the large sliding glass door.

Swivel On Anchor

2.5 star property
2.0 out of 10, (1)
The price is HK$590
HK$1,256 total
includes taxes & fees
13 Aug - 14 Aug
Swivel On Anchor
Tradewinds Beach Resort
Guests can enjoy a serene beach experience with umbrellas and lush vegetation nearby.

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (382)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort
Venice Beach Villas
Relax in our outdoor patio area, featuring a seating arrangement, barbecue grill, and lush greenery.

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (426)
"Everything was great. Great people to work with."
Venice Beach Villas
Yacht Time
Living area

Yacht Time

2.5 star property
2.0 out of 10, (2)
"Regrettably the proper manager never contacted me regarding the check-in instructions and I was not able to stay. If that’s how they do business and I can consider it deplorable. I have requested a full refund and do not recommend this property."
The price is HK$801
HK$1,493 total
includes taxes & fees
24 Aug - 25 Aug
Yacht Time
The Inn On Siesta Key
Relax by the serene pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas for a comfortable stay.

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (181)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The Inn On Siesta Key
Tropical Villas of Venice Beach
Walk along the weathered boardwalk to the serene beach surrounded by lush greenery.

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (238)
"Great Location !!"
Tropical Villas of Venice Beach
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Legacy Trail Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"Staff was so helpful and friendly. Room was beautiful and the art in the hallways was wonderful. I had underestimated the time we would need to catch our AM flight but I would stay here again in the future. We had wonderful conversations with the staff and learned so much from them. "
Jennifer 1-night trip
Posted 17 hours ago
Carlisle Inn