Legacy Trail Holiday Rentals

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Our top choices for Legacy Trail holiday rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (264 reviews)
"Very nice rooms and close to everything. Owner is very welcoming."
United States
Jennifer
The price is NZ$254
includes taxes & fees
27 Apr - 28 Apr
Kon Tiki Inn

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (103 reviews)
"VERY ENJOYABLE /STAFF WAS EXCELLENT"
United States
KARL
The price is NZ$738
includes taxes & fees
21 Apr - 22 Apr
SeaSpray Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,217 reviews)
"Room was clean and well stocked. Staff were easy to access and helpful. Location was great!"
United States
Daniel
The price is NZ$523
includes taxes & fees
12 Apr - 13 Apr
Captiva Beach Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,379 reviews)
"Love the location, excellent service and place clean and quite "
United States
Dayami
The price is NZ$477
includes taxes & fees
23 Apr - 24 Apr
Tropical Beach Resorts

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (478 reviews)
"Exceptional location both to the beach and restaurants. The facility has everything you need to augment your stay: bikes, beach chairs and umbrellas, coolers and pool floats. The room is immaculate too."
United States
Kathy
The price is NZ$268
includes taxes & fees
27 Apr - 28 Apr
Venice Beach Villas

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (612 reviews)
"Great location, phenomenal folks, right on the beach. Walk across the bridge to the restaurants on the water and for some live music. Recommend highly!"
United States
RJ
The price is NZ$371
includes taxes & fees
27 Apr - 28 Apr
A Beach Retreat

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (89 reviews)
"The view was beautiful! "
United States
Jennifer
The price is NZ$707
includes taxes & fees
20 Apr - 21 Apr
Seabreeze at Anna Maria Island Inn

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (441 reviews)
"Incredible location, great room! Loved everything! Would def come back!"
United States
Laís Fernanda
The price is NZ$585
includes taxes & fees
21 Apr - 22 Apr
Haley's at The Anna Maria Island Inn

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (788 reviews)
"So nice to walk to restaurants and shops. Very walkable. Clean. Updated and relaxing atmosphere. Parking was really convenient and accessible. Would stay again."
United States
Deborah
The price is NZ$506
includes taxes & fees
22 Apr - 23 Apr
Bridgewalk Resort

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (245 reviews)
"Staff very accommodating."
United States
Genevieve
The price is NZ$361
includes taxes & fees
22 Apr - 23 Apr
Tropical Villas of Venice Beach

Christian Retreat Conference Center

Christian Retreat Conference Center
3.0 star property
Bradenton
8.8 out of 10, Excellent, (8 reviews)
"A bargain given the cost of other hotels. Nice being hosted by Christians!"
United States
Patrick
The price is NZ$200
includes taxes & fees
19 Apr - 20 Apr
Christian Retreat Conference Center

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,272 reviews)
"Clean room, quiet and in a location convenient to Siesta Key. The pool is very nice, although located at the front of the property alongside a busy road. Would definitely recommend this hotel, especially if a kitchenette is desired."
United States
CAROLYN
The price is NZ$393
includes taxes & fees
12 Apr - 13 Apr
Hibiscus Suites - Gateway to Siesta Key

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (356 reviews)
"Nice beach house center to town and the Main Beach. Beach access across street as well. "
United States
Timothy
The Ringling Beach House

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, (381 reviews)
"Love this place "
United States
Leeanne
The price is NZ$517
includes taxes & fees
12 Apr - 13 Apr
Pelican Post at Anna Maria Island Inn

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (64 reviews)
"We had a wonderful time-perfect location to beach and village. Was nice to come back to a very comfortable and relaxing home. Definitely recommend-5 stars! "
United States
Laura
Siesta Key Island Rentals

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (195 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
The Inn On Siesta Key

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is NZ$1,698
includes taxes & fees
15 Apr - 16 Apr
Gulf View Condominiums

Minorga on the Gulf

Minorga on the Gulf
3.0 star property
Siesta Key Village
Minorga on the Gulf

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (269 reviews)
"Very helpful and nice staff. Lovely room, great location. Adorable cottage"
United States
Hilary
The price is NZ$442
includes taxes & fees
31 Mar - 1 Apr
Casey Key Resort - Gulf Shores

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (41 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is NZ$723
includes taxes & fees
21 Apr - 22 Apr
Siesta Heron Suites & 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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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 favorite 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 depends 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 NZ$254 per night. Entering your travel dates in the search wizard you might find 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.