A wooden pathway surrounded by dense greenery and trees.

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Legacy Trail holiday 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, (6,035 reviews)
"Great resort and location!"
United States
Christine
The price is £151
includes taxes & fees
29 Nov - 30 Nov
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, (2,479 reviews)
"This place was perfect!"
United States
Kat
The price is £113
includes taxes & fees
8 Nov - 9 Nov
Hibiscus Suites - Gateway to Siesta Key
A pathway with wooden posts and ropes, leading to a building with a sign indicating a nautical room.

3. Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (318 reviews)
"Debbie and Sean are excellent hosts. Very clean, very comfortable, very quiet. Pet friendly, which is awesome also. Great location also just a couple miles from downtown or the beach.."
United States
Joseph
The price is £137
includes taxes & fees
8 Nov - 9 Nov
Kon Tiki Inn
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.

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (206 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is £175
includes taxes & fees
17 Nov - 18 Nov
SeaSpray 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, (697 reviews)
"Enjoyed our stay"
United States
Robin
The price is £155
includes taxes & fees
6 Dec - 7 Dec
A Beach Retreat
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

6. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,332 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
United States
Andriy
The price is £142
includes taxes & fees
8 Nov - 9 Nov
Captiva Beach Resort
A compact living space with a kitchen, a dining area, and a sofa with cushions.

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (391 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is £152
includes taxes & fees
18 Nov - 19 Nov
Tiny House Siesta
A beach with a clear sky and calm sea.

8. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (213 reviews)
"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...
United States
Karen Jean
The price is £267
includes taxes & fees
8 Nov - 9 Nov
The Inn On Siesta Key
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

9. 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.
The price is £222
includes taxes & fees
8 Nov - 9 Nov
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.'

10. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (845 reviews)
"I loved this hotel"
United States
Raisare
The price is £256
includes taxes & fees
5 Dec - 6 Dec
Bridgewalk Resort
A beach with a wooden picnic table, palm trees, and a clear blue sea.

11. 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, (169 reviews)
"No oven, but it was an excellent place to stay!"
United States
Brittany K.
The price is £234
includes taxes & fees
16 Nov - 17 Nov
Studio Retreat Across the Street from Beautiful Siesta Key Beach
A beach with clear turquoise water and gentle waves.

12. 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.
The price is £232
includes taxes & fees
7 Nov - 8 Nov
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A beach with a wooden picnic table, palm trees, and a clear blue sea.

13. 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, (192 reviews)
"The property was perfect for our time in Siesta Key. Being right across the road from beach access and having the free trolly pick up/drop off right at the corner of the street was great! Only a quick few minute trolly ride to Siesta Key Village. We would definately stay here again!"
United States
Jacci W.
The price is £280
includes taxes & fees
6 Nov - 7 Nov
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A modern building with a white exterior, a brick gable, and a palm tree in the foreground.

14. 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, (486 reviews)
"Location was perfect"
United States
Amylynn
The price is £136
includes taxes & fees
29 Nov - 30 Nov
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.

15. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Beautiful place"
United States
Chad
The price is £300
includes taxes & fees
6 Nov - 7 Nov
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A beach with tall grasses and a sunset.

16. 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.
The price is £220
includes taxes & fees
4 Dec - 5 Dec
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

17. 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 traveller
Romantic Getaway Beach Club Siesta 202B by RVA
A beach with clear turquoise water and a sandy shore.

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

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (77 reviews)
"great location- clean "
United States
Jon W.
The price is £322
includes taxes & fees
8 Nov - 9 Nov
Siesta Cooler: Only Minutes Walk to Siesta Beach!
A beach with tall grasses and a sunset.

19. 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.
The price is £212
includes taxes & fees
8 Nov - 9 Nov
Beachside Studio Located Across from Main Beach and Half Mile to Village
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.
The price is £270
includes taxes & fees
30 Nov - 1 Dec
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 holiday rentals

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

Legacy Trail holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Legacy Trail holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail holiday rentals we have selected for you start as low as £55 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Legacy Trail rentals

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

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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