A wooden pathway surrounded by dense greenery and trees.

Legacy Trail Holiday Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Legacy Trail holiday rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,937 reviews)
"Amazing resort,"
United States
kurt
The price is HK$1,061
HK$1,402 total
includes taxes & fees
5 Oct - 6 Oct
Tropical Beach Resorts
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (188 reviews)
"Great place with a bunch of little touches that put it above and beyond"
United States
Rafe
The price is HK$1,759
HK$1,987 total
includes taxes & fees
2 Nov - 3 Nov
SeaSpray Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,458 reviews)
"This place was perfect!"
United States
Kat
The price is HK$1,068
HK$1,207 total
includes taxes & fees
5 Oct - 6 Oct
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,314 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is HK$1,224
HK$1,516 total
includes taxes & fees
6 Oct - 7 Oct
Captiva Beach Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (686 reviews)
"Great stay!!"
United States
Genghis
The price is HK$1,446
HK$1,634 total
includes taxes & fees
4 Nov - 5 Nov
A Beach Retreat
A wooden structure with a thatched roof overlooking a beach.

6. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is HK$1,465
HK$1,801 total
includes taxes & fees
18 Oct - 19 Oct
Casey Key Resort
A compact living space with a kitchen, a dining area, and a sofa with cushions.

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is HK$484
HK$1,606 total
includes taxes & fees
8 Oct - 9 Oct
Tiny House Siesta
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

8. House of The Sun Siesta Key Crescent Beach

House of The Sun Siesta Key Crescent Beach
4.0 star property
South Village
8.0 out of 10, Very good, (2 reviews)
"The area is beautiful. The condo was very nice. Has everything in it. You can cook if you prefer. The Gulf of Mexico was right behind the condo walk out on to the beach. It also has a pool. I have no complains I would def go back again . "
United States
Margaret Theresa
The price is HK$2,413
HK$6,181 total
includes taxes & fees
22 Oct - 23 Oct
House of The Sun Siesta Key Crescent Beach
A spacious living room with a leather sofa, a glass coffee table, and a wooden dining table. Large windows provide ample natural light and a view of the outdoors.

9. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is HK$657
HK$2,321 total
includes taxes & fees
5 Oct - 6 Oct
Siesta Heron Suites & Villas
A multi-story building with a light blue facade, featuring a restaurant named 'Bridge Street Bistro' and a sign for 'Island Time.'

10. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (835 reviews)
"I loved this hotel"
United States
Raisare
The price is HK$2,268
HK$2,784 total
includes taxes & fees
6 Oct - 7 Oct
Bridgewalk Resort
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

11. Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (474 reviews)
"Great location and walking distance to the beach"
United States
Francesca
The price is HK$1,347
HK$1,705 total
includes taxes & fees
6 Oct - 7 Oct
Pelican Post at Anna Maria Island Inn
A wooden-paneled room with a round table and four chairs, a flat-screen TV mounted on the wall, and a refrigerator in the background.

12. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is HK$3,531
HK$3,990 total
includes taxes & fees
5 Oct - 6 Oct
Sun Outdoors Sarasota
A modern bedroom with a large bed, a TV mounted on the wall, a wooden headboard, and a view of the sea through the balcony.

13. Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (139 reviews)
"Right on beach, in a good area. Comfy beds, would stay here again"
United States
Katelyn
The price is HK$1,799
HK$2,277 total
includes taxes & fees
5 Oct - 6 Oct
Seabreeze at Anna Maria Island Inn
A modern kitchen with stainless steel appliances, granite countertops, and wooden cabinets.

14. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
The price is HK$596
HK$2,084 total
includes taxes & fees
6 Oct - 7 Oct
Explore Sarasota: Condo w/ Pool Access, Near Dtwn
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

15. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
8.8 out of 10, Excellent, (30 reviews)
"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"
United States
Niovys
The price is HK$1,261
HK$4,944 total
includes taxes & fees
5 Oct - 6 Oct
Chadwick Cove Resort & Marina
A beach with tall grasses and a sunset sky.

16. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is HK$3,076
HK$5,547 total
includes taxes & fees
6 Oct - 7 Oct
Siesta Heron 6 / Sunset
A covered outdoor area with a wooden table and chairs, a white door, and a yellow wall.

17. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
Yellow Palm Cottage, Heart of Siesta Key
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

18. Beach Club at Siesta Key Poolside D

Beach Club at Siesta Key Poolside D
4.0 star property
South Village
9.6 out of 10, Exceptional, (4 reviews)
"Nice getaway. "
United States
Jeff
The price is HK$1,495
HK$4,127 total
includes taxes & fees
8 Oct - 9 Oct
Beach Club at Siesta Key Poolside D
A pair of stacked front-loading washing machines in a commercial setting.

19. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
Beach View 100ft To Beach and SPA
A modern living room with a sofa, coffee table, and artwork on the walls.

20. Pineapple Paradise 1 13 min to Beach Fire Pit

Pineapple Paradise 1 13 min to Beach Fire Pit
2.0 star property
Central Sarasota
The price is HK$900
HK$2,901 total
includes taxes & fees
5 Oct - 6 Oct
Pineapple Paradise 1 13 min to Beach Fire Pit
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.
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Top Legacy Trail Hotel Reviews

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