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Legacy Trail Holiday Rentals

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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, (5,991 reviews)
"This Resort is wonderful"
United States
Liliana
The price is AU$264
includes taxes & fees
21 Oct - 22 Oct
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (199 reviews)
"Best short vacation"
United States
Rommel
The price is AU$327
includes taxes & fees
8 Nov - 9 Nov
SeaSpray Resort

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,471 reviews)
"This place was perfect!"
United States
Kat
The price is AU$205
includes taxes & fees
2 Nov - 3 Nov
Hibiscus Suites - Gateway to Siesta Key

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,324 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is AU$277
includes taxes & fees
21 Oct - 22 Oct
Captiva Beach Resort

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (693 reviews)
"Enjoyed our stay"
United States
Robin
The price is AU$298
includes taxes & fees
4 Nov - 5 Nov
A Beach Retreat

6. 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 AU$380
includes taxes & fees
21 Oct - 22 Oct
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

7. 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, (480 reviews)
"Great location and walking distance to the beach"
United States
Francesca
The price is AU$262
includes taxes & fees
18 Nov - 19 Nov
Pelican Post at Anna Maria Island Inn

8. 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 AU$380
includes taxes & fees
21 Oct - 22 Oct
Siesta Key, Sea Horse Villa, Pool. Daily rentals

9. 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, (168 reviews)
"Perfect location, cozy couples get away."
United States
Hetty B.
The price is AU$392
includes taxes & fees
21 Oct - 22 Oct
Studio Retreat Across the Street from Beautiful Siesta Key Beach

10. 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, (171 reviews)
"Great place to stay right by the beach!"
United States
Justin S.
The price is AU$373
includes taxes & fees
21 Oct - 22 Oct
Beachside Studio Located Across from Main Beach and Half Mile to Village

11. [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)
"Beautiful stay , I walked each day to the beach and really is 13 min walk to get to the beach - pickle ball courts available to play in the morning -the beach is excellent - the place have everything we need beds and shower was really nice -Really excellent we will come back."
United States
Moreixa C.
The price is AU$431
includes taxes & fees
21 Oct - 22 Oct
[lounge like locals] walk to siesta beach +bikes

12. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (841 reviews)
"I loved this hotel"
United States
Raisare
The price is AU$459
includes taxes & fees
25 Oct - 26 Oct
Bridgewalk Resort

13. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
The price is AU$466
includes taxes & fees
21 Oct - 22 Oct
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

14. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
The price is AU$478
includes taxes & fees
21 Oct - 22 Oct
Bright & Beachy–Beach Club Siesta Key 100A by RVA

15. 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 AU$518
includes taxes & fees
9 Nov - 10 Nov
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

16. 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
The price is AU$499
includes taxes & fees
21 Oct - 22 Oct
Romantic Getaway Beach Club Siesta 202B by RVA

17. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (77 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is AU$308
includes taxes & fees
19 Nov - 20 Nov
The "Grouper"

18. Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (140 reviews)
"We loved it and recommend it and definitely plan another. Locals only lol."
United States
Kenneth
The price is AU$473
includes taxes & fees
28 Oct - 29 Oct
Oceanfront Oasis – Longboat Key 226 by RVA

19. Lakeview Resort Condo with Heated Pools & Hot Tubs Near IMG & Anna Maria Island

Lakeview Resort Condo with Heated Pools & Hot Tubs Near IMG & Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (126 reviews)
"Overall great stay!"
United States
Jane H.
The price is AU$434
includes taxes & fees
24 Oct - 25 Oct
Lakeview Resort Condo with Heated Pools & Hot Tubs Near IMG & Anna Maria Island

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 AU$545
includes taxes & fees
21 Oct - 22 Oct
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, 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 favourite 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 depend 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 AU$116 per night. Entering your travel dates in the search wizard might find you 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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