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Holiday Rentals in Legacy Trail

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Our top choices for Legacy Trail holiday rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,775 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is €145
includes taxes & fees
24 Aug - 25 Aug
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, (2,414 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 €117
includes taxes & fees
8 Sept - 9 Sept
Hibiscus Suites - Gateway to Siesta Key

3. 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 €201
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort

4. 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 €160
includes taxes & fees
8 Sept - 9 Sept
Captiva Beach 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 €178
includes taxes & fees
27 Aug - 28 Aug
A Beach Retreat

6. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (384 reviews)
"Great place"
United States
Mario
The price is €192
includes taxes & fees
22 Aug - 23 Aug
Tiny House Siesta

7. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (821 reviews)
"loved it here"
United States
Hannah
The price is €280
includes taxes & fees
8 Sept - 9 Sept
Bridgewalk Resort

8. Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout
South Village
9.8 out of 10, Exceptional, (96 reviews)
"It was all great, really enjoyed our stay."
United States
Roger K.
The price is €768
includes taxes & fees
4 Sept - 5 Sept
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

9. 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 €381
includes taxes & fees
24 Aug - 25 Aug
Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA

10. 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
The price is €333
includes taxes & fees
24 Aug - 25 Aug
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

11. 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 €269
includes taxes & fees
23 Aug - 24 Aug
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

12. 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 €280
includes taxes & fees
23 Aug - 24 Aug
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

13. 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 €257
includes taxes & fees
24 Aug - 25 Aug
Studio Retreat Across the Street from Beautiful Siesta Key Beach

14. 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, (475 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
The price is €149
includes taxes & fees
26 Aug - 27 Aug
Haley's at The Anna Maria Island Inn

15. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is €283
includes taxes & fees
23 Aug - 24 Aug
[lounge like locals] walk to siesta beach +bikes

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 €370
includes taxes & fees
2 Sept - 3 Sept
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

17. Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Dream - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (25 reviews)
"Everything was close and way to get to and from beach,,, great place and Matt was very helpful!"
United States
Warren C.
Sea Dream - 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 €339
includes taxes & fees
23 Aug - 24 Aug
Best views of the beach from your balcony Unit 301

19. 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 €177
includes taxes & fees
8 Sept - 9 Sept
Pelican Post at Anna Maria Island Inn

20. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.4 out of 10, Exceptional, (8 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is €378
includes taxes & fees
24 Aug - 25 Aug
Cedar Run Resort - Roam Hospitality
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 €68 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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