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Legacy Trail Vacation Rentals

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Our top choices for Legacy Trail vacation rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,774 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is CA $182
CA $241 total
includes taxes & fees
Sep 10 - Sep 11
Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,413 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
The price is CA $158
CA $178 total
includes taxes & fees
Aug 25 - Aug 26
Hibiscus Suites - Gateway to Siesta Key

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,299 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is CA $209
CA $259 total
includes taxes & fees
Sep 7 - Sep 8
Captiva Beach Resort

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (173 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is CA $269
CA $304 total
includes taxes & fees
Sep 1 - Sep 2
SeaSpray Resort

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (668 reviews)
"Lovely place on a family beach."
United States
Robert
The price is CA $256
CA $289 total
includes taxes & fees
Aug 27 - Aug 28
A Beach Retreat

6. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (383 reviews)
"Great place"
United States
Mario
The price is CA $107
CA $309 total
includes taxes & fees
Aug 22 - Aug 23
Tiny House Siesta

7. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (78 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is CA $167
CA $511 total
includes taxes & fees
Aug 23 - Aug 24
Siesta Key Island Rentals

8. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (820 reviews)
"loved it here"
United States
Hannah
The price is CA $401
CA $453 total
includes taxes & fees
Sep 8 - Sep 9
Bridgewalk Resort

9. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Brad S.
The price is CA $197
CA $524 total
includes taxes & fees
Aug 23 - Aug 24
Siesta Key Village-Suite #1: A block to the Beach!

10. 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.
The price is CA $257
CA $631 total
includes taxes & fees
Aug 24 - Aug 25
Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA

11. Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
South Village
9.4 out of 10, Exceptional, (38 reviews)
"It was a great location with easy access to the pool, beach and entertainment! The place was clean and nice, perfect for our family!"
United States
Emily
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

12. 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, (447 reviews)
"Great place to stay,"
United States
Wilson
The price is CA $214
CA $270 total
includes taxes & fees
Sep 8 - Sep 9
Pelican Post at Anna Maria Island Inn

13. Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (474 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
The price is CA $189
CA $239 total
includes taxes & fees
Aug 26 - Aug 27
Haley's at The Anna Maria Island Inn

14. 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
The price is CA $265
CA $448 total
includes taxes & fees
Sep 14 - Sep 15
Studio Retreat Across the Street from Beautiful Siesta Key Beach

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

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Siesta Key
9.4 out of 10, Exceptional, (141 reviews)
"Excellent location right across street from beach. Parking spaces are tight, and there is some loud music in surrounding units or businesses."
United States
Michael D.
The price is CA $269
CA $456 total
includes taxes & fees
Aug 23 - Aug 24
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

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
The price is CA $297
CA $586 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

17. 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, (36 reviews)
"Excellent location to everything and the hosts were very accommodating! Will book this place again!"
United States
Christopher B.
The price is CA $461
CA $892 total
includes taxes & fees
Aug 26 - Aug 27
Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

18. Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (93 reviews)
"Everything was great "
United States
kirt v.
The price is CA $228
CA $543 total
includes taxes & fees
Aug 23 - Aug 24
Best views of the beach from your balcony Unit 301

19. Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (117 reviews)
"TCI is a great place to stay. Close to the beach, grocery store, shopping and walking paths. The condo was very clean and has all the amenities needed. The staff if very approachable and easy to connect with for any questions. This is our 2nd stay and we will return."
United States
Anonymous traveller
Sunset and beach view from your balcony Unit 403

20. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (31 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is CA $129
CA $425 total
includes taxes & fees
Aug 23 - Aug 24
[escape to paradise] siesta key beach 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, 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 $111 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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