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
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (5,970 reviews)
"Amazing resort,"
United States
kurt
$150 nightly
The price is $170
Oct 18 - Oct 19
Total with taxes and fees
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,468 reviews)
"This place was perfect!"
United States
Kat
$123 nightly
The price is $139
Oct 19 - Oct 20
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

3. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (197 reviews)
"Best short vacation"
United States
Rommel
$209 nightly
The price is $236
Nov 4 - Nov 5
Total with taxes and fees
SeaSpray Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

4. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (692 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 large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,321 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
$188 nightly
The price is $210
Oct 28 - Oct 29
Total with taxes and fees
Captiva Beach Resort
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

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.
$299 nightly
The price is $333
Oct 16 - Oct 17
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A multi-story building with a light blue facade, featuring a restaurant named 'Bridge Street Bistro' and a sign for 'Island Time.'

7. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (839 reviews)
"I loved this hotel"
United States
Raisare
$314 nightly
The price is $355
Oct 15 - Oct 16
Total with taxes and fees
Bridgewalk Resort
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

8. 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, (477 reviews)
"Great location and walking distance to the beach"
United States
Francesca
$200 nightly
The price is $226
Nov 2 - Nov 3
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

9. Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (90 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
$324 nightly
The price is $361
Oct 15 - Oct 16
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
A wide sandy beach with clear turquoise water and a clear blue sky.

10. THE BEACH CONDO #107 BEACHFRONT FULL VIEW

THE BEACH CONDO #107 BEACHFRONT FULL VIEW
Longboat Key
10.0 out of 10, Exceptional, (101 reviews)
"Beautiful property. Will definitely stay again."
United States
Tami T.
$403 nightly
The price is $451
Oct 17 - Oct 18
Total with taxes and fees
THE BEACH CONDO #107 BEACHFRONT FULL VIEW
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.

11. 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)
"Great location"
United States
Daphane
$349 nightly
The price is $389
Oct 15 - Oct 16
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

12. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (221 reviews)
"Nice stay perfect location"
United States
tom f.
$423 nightly
The price is $471
Oct 21 - Oct 22
Total with taxes and fees
Siesta beach....one and only
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

13. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"Great beach! "
United States
Annie B.
$425 nightly
The price is $474
Oct 15 - Oct 16
Total with taxes and fees
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

14. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (84 reviews)
"The place was super cute, clean, quiet, cozy, and in a great location. The host was very communicative and sweet. Definitely a great stay, 10/10 recommend!"
United States
Sierra B.
$318 nightly
The price is $355
Nov 8 - Nov 9
Total with taxes and fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

15. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
$328 nightly
The price is $335
Oct 18 - Oct 19
Total with taxes and fees
[escape to paradise] siesta key beach getaway
A wooden pathway leading to a beach with lush greenery on either side.

16. 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 18 - Oct 19
Total with taxes and fees
Oceanfront Oasis – Longboat Key 226 by RVA
A beach with a wooden picnic table, palm trees, and a clear blue sea.

17. 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.
$299 nightly
The price is $334
Oct 25 - Oct 26
Total with taxes and fees
Studio Retreat Across the Street from Beautiful Siesta Key Beach
A beachfront property with a house, palm trees, and a view of the ocean.

18. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"Beautiful gulf view."
United States
Audrey B.
$652 nightly
The price is $727
Nov 3 - Nov 4
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A balcony with a view of a beach, a pool, and palm trees.

19. Direct Oceanview: Open October 26th - 29th!

Direct Oceanview: Open October 26th - 29th!
Longboat Key
10.0 out of 10, Exceptional, (137 reviews)
"Great view of the beach and could watch sunset right from balcony, host was awesome, she gave all.kinds of suggestions and was very quick to respond to any questions we had. Would recommend this unit to anyone. They have beach supplies so you dont have to buy any of that. Longboat was very beautiful area."
United States
Gina
$378 nightly
The price is $422
Nov 9 - Nov 10
Total with taxes and fees
Direct Oceanview: Open October 26th - 29th!
A beach with tall grasses and a sunset.

20. 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.
$325 nightly
The price is $362
Nov 9 - Nov 10
Total with taxes and fees
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
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 $93 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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