A wooden pathway surrounded by dense greenery and trees.

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Legacy Trail condo rentals

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

1. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,300 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is €160
includes taxes & fees
10 Sept - 11 Sept
Captiva Beach Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

2. 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
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

3. 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 €267
includes taxes & fees
23 Aug - 24 Aug
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

4. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
8.8 out of 10, Excellent, (80 reviews)
"Beautiful place"
United States
Chad
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

5. Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA

Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
South Village
9.0 out of 10, Wonderful, (76 reviews)
"Great stay. As advertised and very clean!"
United States
Seth S.
The price is €313
includes taxes & fees
22 Aug - 23 Aug
Relax & Unwind – 1BR Beach Club Siesta Key 110D RVA
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.

6. 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
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

7. 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 €408
includes taxes & fees
22 Aug - 23 Aug
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
A beach with a clear sky and calm sea.

8. Siesta Key Condo: Beach, Pool & Village Fun!

Siesta Key Condo: Beach, Pool & Village Fun!
Siesta Key Village
9.2 out of 10, Wonderful, (16 reviews)
"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."
United States
Jeffrey B.
The price is €389
includes taxes & fees
20 Sept - 21 Sept
Siesta Key Condo: Beach, Pool & Village Fun!
A water slide in a pool area with a rocky backdrop and a small waterfall.

9. 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
A beach with tall grasses and a sunset.

10. 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.
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
A beach path leading to the sea with grass on either side.

11. Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (33 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
Jetties Pointe Cottage #5 - 408 “Casey Key”
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

12. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.2 out of 10, Wonderful, (26 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is €502
includes taxes & fees
22 Aug - 23 Aug
Chadwick Cove Resort & Marina
A wooden pathway leading to a beach with lush greenery on either side.

13. Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (108 reviews)
"Great location"
United States
Amy R.
The price is €262
includes taxes & fees
26 Aug - 27 Aug
Oceanfront Bliss–Longboat Key Beach 106 by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

14. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (91 reviews)
"Great location and easy access to the beach."
United States
Erica B.
The price is €312
includes taxes & fees
23 Aug - 24 Aug
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

15. Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (90 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
The price is €307
includes taxes & fees
31 Aug - 1 Sept
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 €309
includes taxes & fees
22 Aug - 23 Aug
Romantic Getaway Beach Club Siesta 202B by RVA
A beach with clear turquoise water and a sandy shore.

17. 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
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

18. 1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach

1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach
South Village
8.8 out of 10, Excellent, (88 reviews)
"Clean and short easy walk to the beach. "
United States
Maureen S.
1BR Pool-View Condo at The Beach Club on Siesta Key | Steps to the beach
A wooden pathway leading to a beach with lush greenery on either side.

19. Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (83 reviews)
"Great beachfront rental in an excellent location, with everything needed for a comfortable stay. The main bed was very comfortable, and the setup works especially well for couples or families with two small children. For us, the second bedroom ended up functioning more as a middle space/changing room, which worked fine, though I do wish there had been a bit more clarity on the layout beforehand, as it’s more of a walk-through area between the living space and main bedroom with a trundle bed...
United States
Patty G.
The price is €300
includes taxes & fees
24 Aug - 25 Aug
Drift & Dune – Longboat Beachfront #101 RVA

20. Stylish Lakefront Retreat By IMG & Anna Maria Island w/ Resort Pools & Hot Tubs

Stylish Lakefront Retreat By IMG & Anna Maria Island w/ Resort Pools & Hot Tubs
Bradenton
10.0 out of 10, Exceptional, (131 reviews)
"It was a perfect location, looked exactly like the pictures and the host did everything to make our stay great!"
United States
Martha B.
Stylish Lakefront Retreat By IMG & Anna Maria Island w/ Resort Pools & Hot Tubs
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

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Legacy Trail Condo Rentals information

Number of reviews
3,004
Accommodation
0 Condo Rentals
Lowest Price
€160
Highest Price
€502

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