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Holiday Rentals in Legacy Trail

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Our top choices for Legacy Trail holiday rentals

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (147 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is €266
includes taxes & fees
19 Jul - 20 Jul
SeaSpray Resort

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (809 reviews)
"Centrally located, all the staff was excellent. Great place to stay! Will stay here again!"
United States
Keri
The price is €317
includes taxes & fees
12 Jul - 13 Jul
Bridgewalk Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,633 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is €190
includes taxes & fees
2 Aug - 3 Aug
Tropical Beach Resorts

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,277 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is €178
includes taxes & fees
2 Aug - 3 Aug
Captiva Beach Resort

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is €316
includes taxes & fees
8 Jul - 9 Jul
The Inn On Siesta Key

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, (462 reviews)
"The property served it's purpose of comfort for relaxation. We enjoyed it thoroughly and will make this an annual trip."
United States
Sydney
The price is €206
includes taxes & fees
4 Aug - 5 Aug
Haley's at The Anna Maria Island Inn

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (646 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is €163
includes taxes & fees
5 Aug - 6 Aug
A Beach Retreat

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, (423 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
The price is €226
includes taxes & fees
9 Jul - 10 Jul
Pelican Post at Anna Maria Island Inn

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,360 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is €134
includes taxes & fees
9 Jul - 10 Jul
Hibiscus Suites - Gateway to Siesta Key

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (72 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is €547
includes taxes & fees
7 Jul - 8 Jul
Cedar Run Resort - Roam Hospitality

Paradise Retreat with HEATED POOL-- Need We Say More

Paradise Retreat with HEATED POOL-- Need We Say More
South Bradenton
10.0 out of 10, Exceptional, (190 reviews)
"Very comfortable will definitely be back!"
United States
Laylah H.
The price is €365
includes taxes & fees
7 Jul - 8 Jul
Paradise Retreat with HEATED POOL-- Need We Say More

THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (93 reviews)
"Host was wondeful!Location and condo fabulous!"
United States
Linda D.
The price is €389
includes taxes & fees
28 Jul - 29 Jul
THE BEACH CONDO #107 BEACHFRONT FULL VIEW

Beach Condo with Pool Near Holmes Beach!

Beach Condo with Pool Near Holmes Beach!
Holmes Beach
9.0 out of 10, Wonderful, (41 reviews)
"Location to the beach"
United States
Joanne C.
Beach Condo with Pool Near Holmes Beach!

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (372 reviews)
"Loved the tiny house will stay there again!"
United States
Nydia
The price is €183
includes taxes & fees
8 Jul - 9 Jul
Tiny House Siesta

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (93 reviews)
"Beautiful condo, great views and fabulous beach access. "
United States
Pamela V.
The price is €662
includes taxes & fees
6 Aug - 7 Aug
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

Mello on the Beach - Sea Duced

Mello on the Beach - Sea Duced
Holmes Beach
9.8 out of 10, Exceptional, (26 reviews)
"Such a great spot! We loved the location, right next to the beach and across the street from the best burger place. The bed was comfy, everything was clean and the kitchen had all we needed. We really loved the beach chairs and towels provided. John, who was on site at the property during our stay, was so friendly and helpful with anything we needed. We will be back!"
Canada
Kristie P.
Mello on the Beach - Sea Duced

Island Time: Open Sun, July 19th, $250/nt + Fees!

Island Time: Open Sun, July 19th, $250/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (130 reviews)
"Gorgeous view! Steps to the beach! The host was so accommodating & had great communication. We would highly recommend!"
United States
Angie T.
The price is €402
includes taxes & fees
19 Jul - 20 Jul
Island Time: Open Sun, July 19th, $250/nt + Fees!

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (82 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
Drift & Dune – Longboat Beachfront #101 RVA

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is €199
includes taxes & fees
7 Jul - 8 Jul
Nestled in North Port. Updated 2 Bed / 1 Bath.
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, apart-hotels, 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 €56 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. 

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