Legacy Trail Vacation Rentals

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Check prices for these dates

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

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, (6,045 reviews)
"Great resort and location!"
United States
Christine
The price is CA $204
CA $267 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $189
CA $214 total
includes taxes & fees
Nov 9 - Nov 10
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, (319 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 CA $230
CA $260 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $301
CA $340 total
includes taxes & fees
Nov 9 - Nov 10
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, (700 reviews)
"Enjoyed our stay"
United States
Robin
The price is CA $260
CA $294 total
includes taxes & fees
Dec 6 - Dec 7
A Beach Retreat
A beach with white sand, wooden beach chairs, and a clear blue sky.

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 CA $218
CA $270 total
includes taxes & fees
Nov 9 - Nov 10
Captiva Beach Resort
A compact living space with a sofa, a television, a ceiling fan, and a door.

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 CA $86
CA $287 total
includes taxes & fees
Nov 22 - Nov 23
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 CA $334
CA $465 total
includes taxes & fees
Nov 10 - Nov 11
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 CA $182
CA $384 total
includes taxes & fees
Nov 9 - Nov 10
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, (847 reviews)
"I loved this hotel"
United States
Raisare
The price is CA $388
CA $478 total
includes taxes & fees
Dec 9 - Dec 10
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 CA $247
CA $430 total
includes taxes & fees
Nov 16 - Nov 17
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 CA $182
CA $384 total
includes taxes & fees
Nov 9 - Nov 10
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)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
The price is CA $267
CA $555 total
includes taxes & fees
Nov 13 - Nov 14
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, (487 reviews)
"Location was perfect"
United States
Amylynn
The price is CA $164
CA $208 total
includes taxes & fees
Dec 9 - Dec 10
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, (82 reviews)
"Beautiful place"
United States
Chad
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 CA $246
CA $410 total
includes taxes & fees
Nov 9 - Nov 10
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 CA $263
CA $565 total
includes taxes & fees
Nov 9 - Nov 10
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.
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 CA $288
CA $511 total
includes taxes & fees
Nov 30 - Dec 1
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

An outdoor seating area with a circular fire pit, wooden chairs, and a pergola structure.
Homewood Suites by Hilton Sarasota Lakewood Ranch

Homewood Suites by Hilton Sarasota Lakewood Ranch

Homewood Suites by Hilton Sarasota Lakewood Ranch
Sarasota

10/10 Excellent

Excellent happy hours five days week and great selection for breakfast
Canada
Ty
Reviewed November 23, 2017
Homewood Suites by Hilton Sarasota Lakewood Ranch

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, cottages, 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 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 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail vacation rentals we have selected for you start as low as CA $85 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 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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