Legacy Trail Holiday Rentals

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Holiday Rentals in Legacy Trail

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5054)
"Clean room, great A/C, close to beach, very quiet, easy parking, close to restaurants, clean beach, very nice staff. "
United States
Marta
The price is AU$254
includes taxes & fees
22 Oct - 23 Oct
Tropical Beach Resorts
Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1144)
"Great place close to the beach"
United States
Yuditza
Captiva Beach Resort
Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (238)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
United States
Carla
The price is AU$262
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2182)
"very nice helpful people at the desk, nice new clean room good parking, walkable to Crescent beach, beautiful beach"
United States
Emanuela
The price is AU$291
includes taxes & fees
21 Nov - 22 Nov
Hibiscus Suites - Gateway to Siesta Key
Pelican Post at Anna Maria Island Inn
3.0 star property
9.2 out of 10, Wonderful, (309)
"Great location, nice rooms, relaxing pool area. Walkable to Bridge Street and the beach."
United States
Angela
Pelican Post at Anna Maria Island Inn
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (292)
"Loved our stay! "
United States
Michelle
The price is AU$822
includes taxes & fees
11 Nov - 12 Nov
The Residences at Siesta Key Beach by Hyatt Vacation Club
Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (333)
"We had a great time at Tiny House, location can not be better and everything was as described."
United States
Elvia
The price is AU$266
includes taxes & fees
22 Oct - 23 Oct
Tiny House Siesta
Haley's at The Anna Maria Island Inn
3.0 star property
8.6 out of 10, Excellent, (379)
"The staff members were so nice and super helpful!! Place was so cute! "
United States
Whitley
Haley's at The Anna Maria Island Inn
Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
United States
Cathy
The price is AU$824
includes taxes & fees
26 Oct - 27 Oct
Chadwick Cove Resort & Marina
Bridgewalk Resort
3.5 star property
9.4 out of 10, Exceptional, (755)
"Great location and staff were knowledgeable about surrounding areas.. "
United States
Denise
The price is AU$443
includes taxes & fees
27 Oct - 28 Oct
Bridgewalk Resort
Siesta Heron Suites & Villas
3.5 star property
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is AU$840
includes taxes & fees
24 Oct - 25 Oct
Siesta Heron Suites & Villas
Seabreeze at Anna Maria Island Inn
3.0 star property
9.0 out of 10, Wonderful, (43)
"Family friendly"
United States
Leslie
Seabreeze at Anna Maria Island Inn
Palm Tree Villas
3.0 star property
9.2 out of 10, Wonderful, (172)
"Lovely property, clean and so close to the beach! Do need a car, for food/dinning. We'll be back."
United States
Nadya
Palm Tree Villas
SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (52)
"Pleasant stay, walk to beach and the Village. Good size mini apartment "
United States
Lisa L
The price is AU$414
includes taxes & fees
26 Oct - 27 Oct
SeaSpray Resort
Casey Key Resort - Gulf Shores
3.0 star property
8.4 out of 10, Very good, (262)
"Amazing place"
United States
Ricardo
Casey Key Resort - Gulf Shores
Alamanda Villas
3.5 star property
10.0 out of 10, Exceptional, (2)
"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$706
includes taxes & fees
22 Oct - 23 Oct
Alamanda Villas
4BR Spacious Paradise
2.0 star property
The price is AU$1,297
includes taxes & fees
22 Oct - 23 Oct
4BR Spacious Paradise
Gulf View Condominiums
3.5 star property
The price is AU$1,540
includes taxes & fees
27 Oct - 28 Oct
Gulf View Condominiums
Bradenton Breeze
4.0 star property
6.0 out of 10, (2)
"It was good! "
United States
Shayna
The price is AU$489
includes taxes & fees
22 Oct - 23 Oct
Bradenton Breeze
Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Lulu's Key House Leatherback 2/2 Downstairs
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

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$254 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.