Legacy Trail Vacation Rentals

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Check prices for these dates

In two weeks
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Legacy Trail vacation rentals

Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (285 reviews)
"Great place to stay!!!"
United States
Tara
$114 nightly
The price is $129
Jun 11 - Jun 12
Total with taxes and fees
Kon Tiki Inn
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,554 reviews)
"Beachy style room - was comfortable - we wished we could stay longer"
Canada
Shelley
$226 nightly
The price is $256
Jun 15 - Jun 16
Total with taxes and fees
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,334 reviews)
"great place to stay for a couple of nights. "
United States
Diana
$141 nightly
The price is $159
Jun 11 - Jun 12
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (640 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
$226 nightly
The price is $255
Jun 14 - Jun 15
Total with taxes and fees
A Beach Retreat
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,262 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
$211 nightly
The price is $236
Jul 6 - Jul 7
Total with taxes and fees
Captiva Beach Resort
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (134 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
$245 nightly
The price is $277
Jun 15 - Jun 16
Total with taxes and fees
SeaSpray Resort
Beach nearby, white sand, beach towels

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, (453 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
$208 nightly
The price is $235
Jun 29 - Jun 30
Total with taxes and fees
Haley's at The Anna Maria Island Inn
2 restaurants; lunch and dinner served

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (807 reviews)
"Centrally located, all the staff was excellent. Great place to stay! Will stay here again!"
United States
Keri
$318 nightly
The price is $359
Jun 30 - Jul 1
Total with taxes and fees
Bridgewalk Resort
Premium bedding, pillowtop beds, minibar, free cribs/infant beds

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (101 reviews)
"Great location!"
United States
Kevin
$291 nightly
The price is $329
Jun 11 - Jun 12
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
Outdoor wedding area

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (275 reviews)
"Great place"
United States
tony
$215 nightly
The price is $242
Jun 12 - Jun 13
Total with taxes and fees
Casey Key Resort - Gulf Shores
Cabin, Balcony, Bay View | Living area

Yacht Time

Yacht Time
2.5 star property
Bradenton
2.0 out of 10, (3 reviews)
"Was never able to check in as the property could not be reached. The number was disconnected."
United States
Gene
$174 nightly
The price is $197
Jun 13 - Jun 14
Total with taxes and fees
Yacht Time
Exterior

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, (408 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
$233 nightly
The price is $263
Jun 11 - Jun 12
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (20 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
$509 nightly
The price is $546
Jun 16 - Jun 17
Total with taxes and fees
Chadwick Cove Resort & Marina
House (2 Bedrooms) | Front of property

2 Mi to Englewood Beach! Home w/ Private Dock

2 Mi to Englewood Beach! Home w/ Private Dock
3.0 star property
Englewood
2 Mi to Englewood Beach! Home w/ Private Dock
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (369 reviews)
"Loved the tiny house will stay there again!"
United States
Nydia
$181 nightly
The price is $205
Jun 14 - Jun 15
Total with taxes and fees
Tiny House Siesta
Interior

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
$2,636 nightly
The price is $2,979
Jun 18 - Jun 19
Total with taxes and fees
3716 7th Ave W
House, Accessible | 4 bedrooms

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
Sarasota Family Home Private Heated Pool Relax
Outdoor pool, pool umbrellas, sun loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
8.0 out of 10, Very Good, (3 reviews)
"I was extremely disappointed with this property. There was mold visible on the outside of the door, and the inside floors were absolutely filthy and appeared not to have been properly cleaned. The bathtub had pubic hair in it, and the shower was also dirty and unsanitary. I called to report the issues and requested to be moved to a different property. The representative who answered said she would call me back, but I didn't receive a return call until six hours later. By that time, I had no...
United States
Suzette
$571 nightly
The price is $645
Jun 15 - Jun 16
Total with taxes and fees
Cedar Run Resort - Roam Hospitality
Exterior

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
9.2 out of 10, Wonderful, (9 reviews)
"The condo was great! Couldn’t have asked for a better place to start our first time in AMI!"
United States
Josephine
$481 nightly
The price is $521
Jun 13 - Jun 14
Total with taxes and fees
Alamanda Villas
Luxury Condo, Beach View | Balcony

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$896 nightly
The price is $973
Jun 27 - Jun 28
Total with taxes and fees
Gulf View Condominiums
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Perfect place to stay . I love this place"
Carlos 2-night trip
Posted 5 hours ago
Kompose Boutique Hotel

Find out more about Legacy Trail

Everything you need to know about Legacy Trail vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Legacy Trail vacation 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 low season months. For more hustle and bustle, you may prefer to visit Legacy Trail in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $129 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail vacation 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 vacation.

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.