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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, (5,835 reviews)
"This place is awesome, super clean close to the beach and the pool small But completely renovated and great"
United States
Diana
The price is AU$248
includes taxes & fees
7 Sept - 8 Sept
Tropical Beach Resorts

2. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (175 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is AU$327
includes taxes & fees
23 Sept - 24 Sept
SeaSpray Resort

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,435 reviews)
"This place was perfect!"
United States
Kat
The price is AU$192
includes taxes & fees
7 Sept - 8 Sept
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, (1,303 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is AU$256
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, (672 reviews)
"Lovely place on a family beach."
United States
Robert
The price is AU$289
includes taxes & fees
7 Sept - 8 Sept
A Beach Retreat

6. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is AU$456
includes taxes & fees
7 Sept - 8 Sept
Siesta Key Island Rentals

7. DOLPHIN PRIVATE HOUSE

DOLPHIN PRIVATE HOUSE
3.0 star property
Siesta Key Village
The price is AU$833
includes taxes & fees
7 Sept - 8 Sept
DOLPHIN PRIVATE HOUSE

8. 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 AU$600
includes taxes & fees
5 Sept - 6 Sept
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

9. 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)
"Good"
United States
Gelsy
The price is AU$648
includes taxes & fees
7 Sept - 8 Sept
2BR Beach Style w Pool Beach Club Siesta 204C RVA

10. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (826 reviews)
"The hotel was wonderful. Nice staff, room and location. Free beach chairs, towels and umbrella to use at the beach which is right across the street."
United States
robin
The price is AU$493
includes taxes & fees
8 Sept - 9 Sept
Bridgewalk Resort

11. 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 close to the beach"
United States
Carleen D.
The price is AU$623
includes taxes & fees
7 Sept - 8 Sept
Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA

12. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"We found this property to be delightful. We loved the balcony for enjoying our evenings. I would have liked to see a table on the balcony for eating at, it is FL, and I wanted to sit outside for my meals. It was a very close walk to the beach, the pool and hot tub were in excellent working condition. We enjoyed the property. We had a problem, but they had maintenance there within an hour to fix it, I call that a win for the property. "
United States
Jackie J.
The price is AU$650
includes taxes & fees
8 Sept - 9 Sept
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

13. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (131 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is AU$657
includes taxes & fees
11 Sept - 12 Sept
Casey Key Beachfront Escape: Charming 1BR Cottage

14. 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, (142 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 AU$435
includes taxes & fees
8 Sept - 9 Sept
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

15. 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$428
includes taxes & fees
13 Sept - 14 Sept
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

16. 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
8.8 out of 10, Excellent, (170 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
The price is AU$369
includes taxes & fees
8 Sept - 9 Sept
Beachside Studio Located Across from Main Beach and Half Mile to 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, (37 reviews)
"Excellent location to everything and the hosts were very accommodating! Will book this place again!"
United States
Christopher B.
The price is AU$883
includes taxes & fees
18 Sept - 19 Sept
Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

18. 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
Studio Retreat Across the Street from Beautiful Siesta Key Beach

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, (454 reviews)
"Great place to stay,"
United States
Wilson
The price is AU$281
includes taxes & fees
22 Sept - 23 Sept
Pelican Post at Anna Maria Island Inn

20. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (33 reviews)
"Easy process in and out. Would definitely do business with them again. A"
United States
Derek J.
The price is AU$389
includes taxes & fees
7 Sept - 8 Sept
[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 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$111 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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