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, (5090)
"Clean, comfortable, and friendly staff."
United States
John
The price is NZ$328
includes taxes & fees
13 Nov - 14 Nov
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, (294)
"Fun place to stay for family vacation "
United States
Todd
The price is NZ$796
includes taxes & fees
11 Dec - 12 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Tiny House Siesta

2.0 star property
Sarasota
8.4 out of 10, Very good, (340)
"The place is very nice and well maintained near the beach"
United States
Laura
The price is NZ$364
includes taxes & fees
7 Dec - 8 Dec
Tiny House Siesta

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
Sarasota
8.6 out of 10, Excellent, (2191)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (241)
"Great place to stay"
United States
Brad
The price is NZ$302
includes taxes & fees
18 Nov - 19 Nov
Kon Tiki Inn

Captiva Beach Resort

3.0 star property
South Village
9.0 out of 10, Wonderful, (1156)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
Captiva Beach Resort

Pelican Post at Anna Maria Island Inn

3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (316)
"Great location"
United States
Michael
The price is NZ$485
includes taxes & fees
30 Nov - 1 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, (388)
"Shampoos conditioners and lotions, beach towels, cleanliness freshness, thank you it was a good day"
United States
Karen
Haley's at The Anna Maria Island Inn

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (335)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
The price is NZ$507
includes taxes & fees
19 Nov - 20 Nov
The Inn On Siesta Key

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (571)
"Perfect location beachfront room"
United States
Suzette
A Beach Retreat

Bridgewalk Resort

3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (759)
"Great stay!"
United States
Sufyan
The price is NZ$569
includes taxes & fees
12 Nov - 13 Nov
Bridgewalk Resort

Island Life! King Bed Studio-Steps to beach

Manasota Key
9.6 out of 10, Exceptional, (168)
"My husband and I stayed at the Bay Breeze Bungalow for 4 days and cannot wait to come back. Perfect location, 2 minute walk to the beach. Quiet neighborhood. We were right next to the pool, and even with kids swimming, it was quiet. We had a question regarding parking, (our confusion) we received a call back within a 1/2 hour. The Bungalow was very clean and had the essentials we needed. Being May, it was extremely warm, the air conditioner always kept the place cool. I cannot say enough...
United States
Karen L.
The price is NZ$382
includes taxes & fees
30 Nov - 1 Dec
Island Life! King Bed Studio-Steps to beach

Riverside Oasis 1Bed/1Bath

Bayou Oaks
9.4 out of 10, Exceptional, (37)
"Perfect little place for a couple days. Clean and conveniently located just a short drive away from everything you need. Host was responsive and accommodating. We would definitely stay here again. "
United States
Adrianne J.
The price is NZ$206
includes taxes & fees
18 Nov - 19 Nov
Riverside Oasis 1Bed/1Bath

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite

Bradenton
9.4 out of 10, Exceptional, (67)
"Everything was great! Check in instructions were very easy."
United States
SARA
The price is NZ$266
includes taxes & fees
12 Nov - 13 Nov
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite

Old Floridian cottage in Historic Gulf Village

Olde Englewood Village
9.8 out of 10, Exceptional, (60)
"Had a nice stay. Clean and well equipped."
United States
Debi D.
The price is NZ$441
includes taxes & fees
14 Nov - 15 Nov
Old Floridian cottage in Historic Gulf Village

Oceanfront Oasis – Longboat Key 226 by RVA

Longboat Key
9.2 out of 10, Wonderful, (119)
"Couldn't have been a better spot for our family"
United States
Sandee R.
The price is NZ$562
includes taxes & fees
7 Dec - 8 Dec
Oceanfront Oasis – Longboat Key 226 by RVA

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Casey Key
9.2 out of 10, Wonderful, (69)
"We so enjoy this little property loved the beach and it’s coziness would definitely refer ones to it and would stay again found lots of shells and sharks teeth"
United States
Bobbie H.
The price is NZ$987
includes taxes & fees
22 Nov - 23 Nov
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Bradenton
10.0 out of 10, Exceptional, (117)
"The condo was beautiful and very spacious. Nice area and very close to the places we wanted to go."
United States
Brenda S.
The price is NZ$524
includes taxes & fees
12 Nov - 13 Nov
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Siesta Key Village
9.8 out of 10, Exceptional, (6)
"We enjoyed the location and beach and had a wonderful relaxing stay. It was nice to be able to bring chairs to the beach and walk a short distance. "
United States
Lillian C.
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
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 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$302 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.