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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Condo Rentals in Legacy Trail

Captiva Beach Resort
Relax in the Captiva chair, surrounded by lush greenery and a stylish sign.

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1122)
"Everything was perfect with our stay. We will be back soon."
Captiva Beach Resort
Venice Beach Villas
Relax in our outdoor patio area, featuring a seating arrangement, barbecue grill, and lush greenery.

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (426)
"Everything was great. Great people to work with."
Venice Beach Villas
Tradewinds Beach Resort
Guests can enjoy a serene beach experience with umbrellas and lush vegetation nearby.

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (382)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort
Anna Maria Sunsets - studio
Enjoy a serene beach experience with access to water activities and a wide, sandy beach perfect for walking or sunbathing.

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (231)
"Perfect retreat from the beach. Wonderful shower, all you need for a beach day staycation."
The price is NZ$390
includes taxes & fees
17 Aug - 18 Aug
Anna Maria Sunsets - studio
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Enjoy a tranquil beach experience with a wide, sandy beach and calm ocean views.

Beach front 2 bed-2 bath private balcony, modern with Gulf front views

8.8 out of 10, Excellent, (21)
"Great view and nice place for a short stay. "
The price is NZ$783
includes taxes & fees
18 Aug - 19 Aug
Beach front 2 bed-2 bath private balcony, modern with Gulf front views
Anna Maria Beach Condo 1/1
Enjoy a serene beach experience with clear waters and a wide, sandy shore, perfect for relaxation and water activities.

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (223)
"This is a great condo. Super clean, super spacious. Host was very responsive. It’s right across the street from the beach. I highly recommend and would stay again."
The price is NZ$552
includes taxes & fees
15 Aug - 16 Aug
Anna Maria Beach Condo 1/1
Take a Peek at a fabulous unit.
Enjoy breathtaking ocean views from your balcony amidst lush palm trees and a serene beachfront setting.

Take a Peek at a fabulous unit.

10.0 out of 10, Exceptional, (122)
"You can not get any closer to the beach than this. The view, the room and our property manager were all amazing. ZERO complaints. Can't wait to go back. "
Take a Peek at a fabulous unit.
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
Enjoy a tranquil seaside escape with a beachfront view of the ocean and lush greenery.

DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.

10.0 out of 10, Exceptional, (90)
"A beautiful view with amazing comfort in the condo! I can’t wait to come back!❤️😎"
DIRECTLY ON PRIVATE BEACH! AMAZING PANORAMIC GULF VIEWS! MODERN, COZY CONDO.
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
Enjoy access to the ocean from this beachfront property.

DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!

9.8 out of 10, Exceptional, (58)
"Really nice property. So glad it survived the hurricane. Can’t wait to stay there again. "
DIRECTLY ON PRIVATE BEACH! GULF VIEW CONDO! Amazing panoramic sunset views!
Anna Maria Sunsets - studio
Relax on a wooden deck overlooking the beach and ocean.

Anna Maria Sunsets - studio

9.2 out of 10, Wonderful, (213)
" Very clean great location and property owner very nice and understanding thank you for everything "
The price is NZ$422
includes taxes & fees
19 Aug - 20 Aug
Anna Maria Sunsets - studio
Anna Maria Island - 2/1
Situated on the beach, this pavilion offers a tranquil retreat with a checkered roof and wooden floor.

Anna Maria Island - 2/1

9.6 out of 10, Exceptional, (167)
"Property worked great for our family "
The price is NZ$571
includes taxes & fees
10 Aug - 11 Aug
Anna Maria Island - 2/1
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
Relax on the balcony overlooking the beach, where a pool and lounge chairs await.

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

9.0 out of 10, Wonderful, (17)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
The price is NZ$704
includes taxes & fees
10 Aug - 11 Aug
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Relax on the wide, open beach with comfortable beach tents and umbrellas.

1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets

9.6 out of 10, Exceptional, (157)
"We could not have been happier with this location and its proximity to the beach and the pools. It was also close to great restaurants by locals who proudly serve great food!! "
1 BR/1 BA Condo on Siesta Key .Sleeps 4.Heated pools.Tennis courts.WIFI. No pets
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
Guests can enjoy a serene beach experience with clear blue waters and soft sandy shores.

Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building

9.8 out of 10, Exceptional, (259)
"Great location! Beautiful beach! "
Oceanfront/Beachfront -Sarasota Surf Racquet - Y Building
Beachfront Directly on Bradenton Beach
Enjoy ocean views from this elevated deck featuring a table and chairs.

Beachfront Directly on Bradenton Beach

9.6 out of 10, Exceptional, (23)
"Very nice location to stay. Only issue we had was parking was very tight so prepare for that if you have a large suv or truck. "
The price is NZ$1,122
includes taxes & fees
24 Aug - 25 Aug
Beachfront Directly on Bradenton Beach
Prime Beachfront with Views, Views, Views!
Enjoy breathtaking views of the ocean from your balcony overlooking the white sandy beach and lush green lawn.

Prime Beachfront with Views, Views, Views!

9.6 out of 10, Exceptional, (82)
"The condo was clean, nicely decorated, spacious and very comfortable! It was steps from the beach and pool! The beach is absolutely beautiful! The pool was very nice! We would definitely stay here again! The beds are very comfortable and having two full bathrooms was so nice! We had a great week! "
Prime Beachfront with Views, Views, Views!
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Relax by the pool surrounded by palm trees and enjoy a refreshing swim.

Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club

9.8 out of 10, Exceptional, (28)
"It was a magical trip and we’ve already booked for next year!!!"
Island Time 504 Siesta Key Beach located Sarasota Surf & Racquet Club
Sand in Your Toes . . . Right Out Your Front Door!
Relax in a serene outdoor seating area with a table and benches, shaded by a palm tree and offering a view of the ocean.

Sand in Your Toes . . . Right Out Your Front Door!

9.4 out of 10, Exceptional, (113)
"Clean & comfortable with the beach just steps away!"
Sand in Your Toes . . . Right Out Your Front Door!
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
Enjoy the serene beach experience with gentle waves lapping at the shore.

Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC

6.6 out of 10, (7)
"Great location and beach access- pool is awesome! Unit doesn’t face the ocean, but it’s right there! Very low key- place is very clean. WiFi is spotty and would not be good if you are planning to work while staying- that is an island wide issue I believe- No stove, but has everything else a kitchen needs and a grill- we would come back! "
The price is NZ$781
includes taxes & fees
11 Aug - 12 Aug
Charming 1-bedroom, beachfront condo in serene Longboat Key with WiFi, AC
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
Cozy living area with sofa, dining table for four, and a large flat-screen TV.

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (93)
"Lovely unit and the perfect location. Short walk to the beach and easy to get to the shopping/eating areas. "
The price is NZ$742
includes taxes & fees
1 Sept - 2 Sept
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"El desayuno. Huevos revueltos. Seria una mejor option."
Alfredo 3-night trip
Posted 1 day ago
Spark by Hilton Sarasota Siesta Key Gateway