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
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (5,805 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
$134 nightly
The price is $152
Aug 31 - Sep 1
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
8.6 out of 10, Excellent, (2,433 reviews)
"This place was perfect!"
United States
Kat
$123 nightly
The price is $139
Aug 30 - Aug 31
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, (175 reviews)
$202 nightly
The price is $228
Sep 2 - Sep 3
Total with taxes and fees
SeaSpray Resort
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, (1,302 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
$167 nightly
The price is $187
Sep 1 - Sep 2
Total with taxes and fees
Captiva Beach Resort
A beach with a clear sky and calm sea.

5. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (205 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
$245 nightly
The price is $277
Aug 31 - Sep 1
Total with taxes and fees
The Inn On Siesta Key
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

6. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (671 reviews)
"Lovely place on a family beach."
United States
Robert
$205 nightly
The price is $231
Aug 31 - Sep 1
Total with taxes and fees
A Beach Retreat
A wooden pathway leading to a beach with clear turquoise water and a wooden railing on one side.

7. Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (268 reviews)
"It was amazing and way beyond what I thought. Easy walk to beach(0.4 mikes) and shops. Private location with small pool. Just what you need."
United States
Christina
$118 nightly
The price is $133
Aug 30 - Aug 31
Total with taxes and fees
Tropical Villas of Venice Beach
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

8. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
$283 nightly
The price is $320
Aug 31 - Sep 1
Total with taxes and fees
Siesta Key Island Rentals

9. DOLPHIN PRIVATE HOUSE

DOLPHIN PRIVATE HOUSE
3.0 star property
Siesta Key Village
$531 nightly
The price is $600
Aug 30 - Aug 31
Total with taxes and fees
DOLPHIN PRIVATE HOUSE
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

10. 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)
"We found this property to be delightful. We loved the balcony for enjoying our evenings. I would have liked to see a table on the balcony for eating at, it is FL, and I wanted to sit outside for my meals. It was a very close walk to the beach, the pool and hot tub were in excellent working condition. We enjoyed the property. We had a problem, but they had maintenance there within an hour to fix it, I call that a win for the property. "
United States
Jackie J.
$429 nightly
The price is $478
Aug 30 - Aug 31
Total with taxes and fees
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

11. Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA

Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA
South Village
9.2 out of 10, Wonderful, (103 reviews)
"Very clean, tons of beach towels, and very easy to check in. Would recommend."
United States
Michele G.
$410 nightly
The price is $457
Aug 30 - Aug 31
Total with taxes and fees
Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA
A two-story building with a balcony, palm trees, and outdoor seating.

12. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (825 reviews)
"The hotel was wonderful. Nice staff, room and location. Free beach chairs, towels and umbrella to use at the beach which is right across the street."
United States
robin
$286 nightly
The price is $323
Aug 30 - Aug 31
Total with taxes and fees
Bridgewalk Resort
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.

13. 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, (99 reviews)
"Great location"
United States
Daphane
$343 nightly
The price is $382
Aug 31 - Sep 1
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

14. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (130 reviews)
"A beautiful location and super comfortable!"
United States
K B.
$409 nightly
The price is $456
Aug 30 - Aug 31
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
An aerial view of a beach with clear turquoise waters, a sandy shore, and a coastal town with buildings and greenery.

15. Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
10.0 out of 10, Exceptional, (37 reviews)
"Excellent location to everything and the hosts were very accommodating! Will book this place again!"
United States
Christopher B.
$577 nightly
The price is $643
Aug 30 - Aug 31
Total with taxes and fees
Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
A beach with a wooden picnic table, palm trees, and a clear blue sea.

16. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (190 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$386 nightly
The price is $430
Sep 2 - Sep 3
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A beach with clear turquoise water and a sandy shore.

17. Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (75 reviews)
"great location- clean "
United States
Jon W.
$373 nightly
The price is $403
Aug 30 - Aug 31
Total with taxes and fees
Siesta Cooler: Only Minutes Walk to Siesta Beach!
A beach with a wooden picnic table, palm trees, and a clear blue sea.

18. 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, (167 reviews)
"It was a great place. And just about a 5 min walk to the beach. "
United States
DESIREE
$258 nightly
The price is $287
Sep 1 - Sep 2
Total with taxes and fees
Studio Retreat Across the Street from Beautiful Siesta Key Beach
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

19. 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.
$229 nightly
The price is $255
Aug 31 - Sep 1
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.

20. 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, (452 reviews)
"Great place to stay,"
United States
Wilson
$163 nightly
The price is $185
Sep 22 - Sep 23
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
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 $90 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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