Search Holiday Rentals in Legacy Trail

Start date: Check-in selected.
End date: Check-out
    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

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Top Holiday Rentals in Legacy Trail

Our top choices for Legacy Trail holiday rentals

Tropical Beach Resorts
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4949)
"Wonderful resort "
The price is ₹12,304
₹15,898 total
includes taxes & fees
8 Sept - 9 Sept
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2169)
"Friendly staff, room was really clean!"
Hibiscus Suites - Gateway to Siesta Key
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1128)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort
SeaSpray Resort
Deluxe Suite, 2 Bedrooms | Living area

SeaSpray Resort

4.0 star property
9.6 out of 10, Exceptional, (32)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
The price is ₹20,212
₹22,840 total
includes taxes & fees
8 Sept - 9 Sept
SeaSpray Resort
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (321)
"Its a nice little family spot"
The Ringling Beach House
Pelican Post at Anna Maria Island Inn
Exterior

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (298)
"Place was very clean and perfect location for the beach/surrounding restaurants."
Pelican Post at Anna Maria Island Inn
Seabreeze at Anna Maria Island Inn
Exterior

Seabreeze at Anna Maria Island Inn

3.0 star property
9.0 out of 10, Wonderful, (34)
"Awesome place to stay "
Seabreeze at Anna Maria Island Inn
Tiny House Siesta
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (321)
"Place was great close to all locations Was a fun tiny experience I recommend. Sarasota was excellent "
The price is ₹6,990
₹12,886 total
includes taxes & fees
8 Sept - 9 Sept
Tiny House Siesta
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (229)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
Kon Tiki Inn
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (128)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach
Bridgewalk Resort
Outdoor pool, pool umbrellas, pool loungers

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (738)
"Very nice rooms and location "
The price is ₹22,885
₹25,860 total
includes taxes & fees
9 Sept - 10 Sept
Bridgewalk Resort
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (43)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing
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, (286)
"Great location. Everyone was very friendly and accommodating!"
The price is ₹34,886
₹43,910 total
includes taxes & fees
29 Sept - 30 Sept
The Residences at Siesta Key Beach by Hyatt Vacation Club
Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (47)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is ₹10,040
₹24,380 total
includes taxes & fees
8 Sept - 9 Sept
Siesta Key Island Rentals
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (434)
"Clean and welcoming property"
Venice Beach Villas
Tradewinds Beach Resort
Private beach nearby, sun-loungers, beach towels

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (383)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On Siesta Key
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach
Yacht Time
Cabin, Balcony, Bay View | 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 ₹10,592
₹18,588 total
includes taxes & fees
8 Sept - 9 Sept
Yacht Time
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
"Very good hotel."
MAURICE 3-night trip
Posted 5 days ago
Carlisle Inn

Find out more about Legacy Trail

Find out more about Legacy Trail

Holiday Rentals in Legacy Trail

Search for holiday rentals in Legacy Trail on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Legacy Trail using one of the methods below:

  • View our selection of featured holiday rentals in Legacy Trail
  • Use the map to find apartments and other holiday homes in the Legacy Trail neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Legacy Trail while they last

Look no further and take a look at our great range of rental properties in Legacy Trail!