Legacy Trail Holiday Rentals

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Holiday Rentals in Legacy Trail

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5137)
"Wonderful trip! Great location! Great staff!"
United States
Kevin
The price is AU$264
includes taxes & fees
9 Dec - 10 Dec
Tropical Beach Resorts

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (298)
"Loved our stay! "
United States
Michelle
The price is AU$735
includes taxes & fees
16 Dec - 17 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
Sarasota
8.6 out of 10, Excellent, (2205)
"This place is a gem!! I only stayed one night but wish it was more. The room was very clean and the staff was fantastic. The area is beautiful and at an excellent price. I highly recommend you stay here if you are in Siesta Keys!!"
United States
Ryan
Hibiscus Suites - Gateway to Siesta Key

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (245)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
The price is AU$277
includes taxes & fees
15 Dec - 16 Dec
Kon Tiki Inn

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (342)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House

Pelican Post at Anna Maria Island Inn

3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (326)
"Fabulous stay! Super clean!"
United States
Sarah
The price is AU$632
includes taxes & fees
26 Dec - 27 Dec
Pelican Post at Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (398)
"Super stay! Clean cute room…very short walk to spectacular beach! We’ll be back!"
United States
Imre
The price is AU$789
includes taxes & fees
26 Dec - 27 Dec
Haley's at The Anna Maria Island Inn

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (576)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
A Beach Retreat

Tiny House Siesta

2.0 star property
Sarasota
8.4 out of 10, Very good, (344)
"Enjoyable stay. "
United States
Lori
The price is AU$365
includes taxes & fees
16 Dec - 17 Dec
Tiny House Siesta

Casey Key Resort - Gulf Shores

3.0 star property
Casey Key
8.4 out of 10, Very good, (264)
"Amazing place"
United States
Ricardo
Casey Key Resort - Gulf Shores

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (190)
"Great place to stay! "
United States
Carlos
The price is AU$464
includes taxes & fees
7 Dec - 8 Dec
The Inn On Siesta Key

Bridgewalk Resort

3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (766)
"Great stay!"
United States
Sufyan
The price is AU$437
includes taxes & fees
11 Dec - 12 Dec
Bridgewalk Resort

Relax in Hot Tub, Walk to Springs: North Port Home

3.0 star property
North Port
The price is AU$338
includes taxes & fees
15 Dec - 16 Dec
Relax in Hot Tub, Walk to Springs: North Port Home

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$526
includes taxes & fees
18 Dec - 19 Dec
Siesta Heron Suites & Villas

SeaSpray Resort

4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (72)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
The price is AU$424
includes taxes & fees
9 Dec - 10 Dec
SeaSpray Resort

Seabreeze at Anna Maria Island Inn

3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (55)
"Nice Place "
United States
Rafael
The price is AU$431
includes taxes & fees
7 Dec - 8 Dec
Seabreeze at Anna Maria Island Inn

Palm Tree Villas

3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (172)
"1 block from the beach, the villa had everything we needed."
United States
Jeana
Palm Tree Villas

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (52)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is AU$504
includes taxes & fees
7 Dec - 8 Dec
Siesta Key Island Rentals

Alamanda Villas

3.5 star property
Holmes Beach
10.0 out of 10, Exceptional, (3)
"The location is wonderful for beach access,places to eat and grocery is block away. Small parking area if more than one couple stay. Had a great stay."
United States
Traci
The price is AU$687
includes taxes & fees
7 Dec - 8 Dec
Alamanda Villas
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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Find out more about Legacy Trail

Everything you need to know about Legacy Trail holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Legacy Trail holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Legacy Trail holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Legacy Trail. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Legacy Trail holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail holiday rentals we have selected for you start as low as AU$264 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Legacy Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Legacy Trail holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Legacy Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.