Legacy Trail Vacation Rentals

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Check prices for these dates

Tonight
Dec 14 - Dec 15
Tomorrow
Dec 15 - Dec 16
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Legacy Trail vacation rentals

Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5149)
"Great place, easy beach access and property was beautiful. "
United States
Maria
$147 nightly
The price is $166
Dec 15 - Dec 16
Total with taxes and fees
Tropical Beach Resorts
Front of property - evening/night
Captiva Beach Resort

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1172)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
$153 nightly
The price is $171
Dec 15 - Dec 16
Total with taxes and fees
Captiva Beach Resort
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

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2212)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
$150 nightly
The price is $170
Dec 15 - Dec 16
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi
SeaSpray Resort

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (77)
"Perfect location, helpful staff, awesome place! "
United States
Mark Gregory
$309 nightly
The price is $349
Dec 15 - Dec 16
Total with taxes and fees
SeaSpray Resort
Property grounds
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (299)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
$441 nightly
The price is $498
Jan 14 - Jan 15, 2026
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
Exterior
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (329)
"Fabulous stay! Super clean!"
United States
Sarah
$209 nightly
The price is $236
Dec 15 - Dec 16
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Front of property
The Ringling Beach House

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (344)
"great location, very clean, quiet"
United States
Joaquin
$340 nightly
The price is $385
Dec 24 - Dec 25
Total with taxes and fees
The Ringling Beach House
Beach nearby, white sand, sun loungers, beach towels
Haley's at The 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, (399)
"Beautiful location. Walking distance to beach. "
United States
Maria
$148 nightly
The price is $167
Dec 18 - Dec 19
Total with taxes and fees
Haley's at The Anna Maria Island Inn
2 restaurants, lunch, dinner served; seafood
Bridgewalk Resort

Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (766)
"Great stay!"
United States
Sufyan
$269 nightly
The price is $304
Jan 10 - Jan 11, 2026
Total with taxes and fees
Bridgewalk Resort
Premium bedding, pillowtop beds, free WiFi, bed sheets
Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (57)
"Everything was great!!!!"
United States
David
$185 nightly
The price is $209
Dec 17 - Dec 18
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (346)
"Enjoyable stay. "
United States
Lori
$212 nightly
The price is $239
Dec 15 - Dec 16
Total with taxes and fees
Tiny House Siesta
Exterior
Alamanda Villas

Alamanda Villas

Alamanda Villas
3.5 star property
Holmes Beach
10.0 out of 10, Exceptional, (3)
"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
$426 nightly
The price is $460
Dec 15 - Dec 16
Total with taxes and fees
Alamanda Villas
Terrace/patio
Kon Tiki Inn

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (246)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
$137 nightly
The price is $155
Dec 22 - Dec 23
Total with taxes and fees
Kon Tiki Inn
Exterior
Siesta Key Island Rentals

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (53)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
$275 nightly
The price is $310
Dec 18 - Dec 19
Total with taxes and fees
Siesta Key Island Rentals
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, individually decorated
A Beach Retreat

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (576)
"Location, very clean and comfortable. Nice efficiency."
United States
Chuck
$184 nightly
The price is $208
Dec 17 - Dec 18
Total with taxes and fees
A Beach Retreat
Comfort Cabin, Bay View | Living area
Swivel On Anchor

Swivel On Anchor

Swivel On Anchor
2.5 star property
Bradenton
2.0 out of 10, (2)
"Was supposed to depart at 6. I showed up at 5:15 and waited until 6 before i started calling their phone number. Had to call 15 times before i got an answer and they said they didnt know i booked it. Said they would have a captain out in 40 minutes. Called me back 20 minutes later to tell me they didnt have a captain. This was 2 weeks ago and i still haven't received a refund. There's either super unprofessional or scam artists."
United States
Chris
$155 nightly
The price is $175
Dec 15 - Dec 16
Total with taxes and fees
Swivel On Anchor
Beach nearby, white sand, beach umbrellas, beach towels
The Inn On Siesta Key

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
$227 nightly
The price is $257
Dec 15 - Dec 16
Total with taxes and fees
The Inn On Siesta Key
Beach nearby, white sand, sun loungers, beach umbrellas
Siesta Palms By the Beach

Siesta Palms By the Beach

Siesta Palms By the Beach
3.5 star property
South Village
9.4 out of 10, Exceptional, (137)
"Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!"
United States
Lynn
Siesta Palms By the Beach
Fridge, microwave, oven, stovetop
3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.

3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.

3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.
Siesta Key
8.4 out of 10, Very Good, (5)
$289 nightly
The price is $322
Dec 15 - Dec 16
Total with taxes and fees
3-bedroom 2-bathroom Siesta Key townhome close to beaches, city and airport.
Beach nearby, beach umbrellas, beach towels
Tropical Villas of Venice Beach

Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (241)
"Clean, but very outdated. "
United States
Tim
Tropical Villas of Venice Beach
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

SeaSpray Resort

SeaSpray Resort

10/10 Excellent
"Room was wonderful, so much space. Great distance to beach (with beach amenities included) and walking distance to bars and restaurants. "
Leah Ferris 3-night trip
Posted 2 days ago
SeaSpray Resort

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 $155 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.

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