A wooden pathway surrounded by dense greenery and trees.

Legacy Trail Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Legacy Trail vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,007 reviews)
"This Resort is wonderful"
United States
Liliana
$158 nightly
The price is $179
Nov 24 - Nov 25
Total with taxes and fees
Tropical Beach Resorts
A bedroom with a view of a swimming pool and outdoor seating.

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (201 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
$206 nightly
The price is $233
Nov 2 - Nov 3
Total with taxes and fees
SeaSpray Resort
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,472 reviews)
"This place was perfect!"
United States
Kat
$117 nightly
The price is $132
Nov 8 - Nov 9
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,325 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
$173 nightly
The price is $194
Oct 28 - Oct 29
Total with taxes and fees
Captiva Beach Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (694 reviews)
"Enjoyed our stay"
United States
Robin
$205 nightly
The price is $231
Nov 4 - Nov 5
Total with taxes and fees
A Beach Retreat
A house with a gravel driveway, two blue chairs facing the front, and a porch with a green chair and a red umbrella.

6. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
$238 nightly
The price is $265
Oct 25 - Oct 26
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

7. 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, (481 reviews)
"Great location and walking distance to the beach"
United States
Francesca
$203 nightly
The price is $229
Nov 2 - Nov 3
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Two blue chairs facing a house with a porch, surrounded by palm trees and a gravel driveway.

8. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
$238 nightly
The price is $265
Oct 25 - Oct 26
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A compact living space with a kitchenette, a dining area, and a bedroom.

9. Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
9.0 out of 10, Wonderful, (168 reviews)
"Perfect location, cozy couples get away."
United States
Hetty B.
$262 nightly
The price is $293
Oct 25 - Oct 26
Total with taxes and fees
Studio Retreat Across the Street from Beautiful Siesta Key Beach
A modern kitchen with white cabinetry, a black countertop, and a built-in microwave.

10. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
9.0 out of 10, Wonderful, (172 reviews)
"Great place to stay right by the beach!"
United States
Justin S.
$230 nightly
The price is $257
Oct 26 - Oct 27
Total with taxes and fees
Beachside Studio Located Across from Main Beach and Half Mile to Village
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

11. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
$287 nightly
The price is $292
Oct 26 - Oct 27
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes
A balcony with a table and chairs, overlooking a beach with palm trees and a blue building with an American flag.

12. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (842 reviews)
"I loved this hotel"
United States
Raisare
$314 nightly
The price is $355
Oct 26 - Oct 27
Total with taxes and fees
Bridgewalk Resort
A pool area with palm trees, a small pool, and a wooden fence.

13. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
$297 nightly
The price is $331
Oct 25 - Oct 26
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A pool area with palm trees, a small pool, and a wooden fence.

14. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
$309 nightly
The price is $344
Oct 27 - Oct 28
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA
A modern hotel room with a bed, a TV displaying a beach scene, a dining area, and a small table with a decorative item.

15. Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Siesta Key
9.2 out of 10, Wonderful, (145 reviews)
"We loved it!"
United States
John S.
$277 nightly
The price is $309
Oct 28 - Oct 29
Total with taxes and fees
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
A pool area with palm trees, a small pool, and a wooden fence.

16. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA
South Village
8.8 out of 10, Excellent, (57 reviews)
"Peaceful getaway. Throughly enjoyed the stay. "
United States
Anonymous traveler
$318 nightly
The price is $355
Oct 25 - Oct 26
Total with taxes and fees
Romantic Getaway Beach Club Siesta 202B by RVA
A covered patio area with wicker furniture, a metal table, and a view of a grassy yard.

17. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (78 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
$191 nightly
The price is $213
Oct 25 - Oct 26
Total with taxes and fees
The "Grouper"
A pool area with a view of the beach, surrounded by palm trees and greenery.

18. Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (140 reviews)
"We loved it and recommend it and definitely plan another. Locals only lol."
United States
Kenneth
$301 nightly
The price is $336
Oct 28 - Oct 29
Total with taxes and fees
Oceanfront Oasis – Longboat Key 226 by RVA
A golf course with multiple water hazards, surrounded by buildings and a beach.

19. Lakeview Corner Condo Near IMG & Anna Maria Island with Heated Pools & Hot Tubs

Lakeview Corner Condo Near IMG & Anna Maria Island with Heated Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (127 reviews)
"Overall great stay!"
United States
Jane H.
$268 nightly
The price is $299
Oct 25 - Oct 26
Total with taxes and fees
Lakeview Corner Condo Near IMG & Anna Maria Island with Heated Pools & Hot Tubs
A room with a sliding glass door leading to an outdoor area with a pool and chairs. There is a brown leather sofa with patterned cushions and a framed picture on the wall.

20. Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (100 reviews)
"The place was excellent!!! Very beautiful and close to the beach. Super cozy. It was perfect and just what I had in mind."
United States
Amy P.
$337 nightly
The price is $376
Nov 9 - Nov 10
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
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 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 $88 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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