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Compare 850 Vacation Homes in Legacy Trail with updated reviews, rates, and availability.

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (217)
"Good location clean easy check in"
Tropical Villas of Venice Beach

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (29)
"I love this property and people that run it are awesome. Paige you never left me hanging on anything you always answered my questions or problems immediately. Thank You"
Siesta Key Island Rentals

2-Bedroom Pool Home Convenient To Beaches

9.8 out of 10, Exceptional, (117)
"Super easy to rent - host very responsive. Basic accommodation with bonus swimming pool. Nice privacy factor. Convenient for our weekend trip to view area properties. "
2-Bedroom Pool Home Convenient To Beaches

Amazing heated pool & spa just minutes from Anna Maria Island

9.6 out of 10, Exceptional, (26)
"My wife and I have stayed in several VRBOs in Bradenton. This property was perfect relative to space and amenities. The pool and spa was amazing and my 89 year old mom loved it. There is a cost to heat the water but well worth the nominal cost. The hosts responded quickly to text and messaging. We loved this place."
The price is SAR 1,127
SAR 2,479 total
includes taxes & fees
28 Dec - 29 Dec
Amazing heated pool & spa just minutes from Anna Maria Island

Cute Bungalow close to downtown and Anna Maria Island.

10.0 out of 10, Exceptional, (13)
"This house was awesome! We were in town for our granddaughter’s Lacrosse tournament and this house was a life saver. We were able to do laundry and it was so convenient to both fields. I would come stay again for vacay. It was so nice and cozy!"
Cute Bungalow close to downtown and Anna Maria Island.

Backyard Oasis & Resort Style Pool

10.0 out of 10, Exceptional, (10)
"A time was had at this beautiful home! There is a smell like someone had a dog the past stay, but overall the vibes of this home is immaculate and you will definitely see me again soon. The host Brandon is someone who won’t disappoint if you’re looking for a chill spot, it’s definitely going to be this one. Love the salt water pool it’s not too deep for those with kids. Loved everything about this spot and hope you all get to experience it!"
Backyard Oasis & Resort Style Pool

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.8 out of 10, Exceptional, (77)
"We stayed for 5 nights and wished we could have stayed longer! The home was perfect for our needs with spacious rooms, clean and well taken care of, and all the amenities we could use. The pool and canal view were added bonuses. The location was especially great for us. We walked daily to the Village to enjoy the variety of restaurants and also the gorgeous public beach. The host was so responsive to questions and also helped us with a forgotten item. Above and beyond! Recommend so...
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

9.2 out of 10, Wonderful, (35)
"This was a great home to stay in! My friend and I were in town for a birthday. The neighborhood is very safe and close to so many local spots. The owners were very responsive and helpful. "
The price is SAR 526
SAR 1,481 total
includes taxes & fees
1 Dec - 2 Dec
Gorgeous Pool house 5 min from the beach, shopping and restaurants I

Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach

10.0 out of 10, Exceptional, (129)
"Enjoyed our stay very much. Only downside the pool was a Littel cold."
Comfy private home In Venice, Florida -Solar Heated Pool, Minutes From the Beach

A Piece of Heaven, Waterfront Home, Heated Screened Pool & in Port Charlotte

9.2 out of 10, Wonderful, (58)
"Great property. Owner was attentive and accessible. "
The price is SAR 515
SAR 1,018 total
includes taxes & fees
2 Dec - 3 Dec
A Piece of Heaven, Waterfront Home, Heated Screened Pool & in Port Charlotte

Private Home | Dog Allowed | Outdoor Seating | W/D, Close to Beach & Village Shops

9.6 out of 10, Exceptional, (38)
"Trip was to help w family medical emergency- close to hospital but also to downtown, beaches etc. Perfect oasis from a stressful situation"
Private Home | Dog Allowed | Outdoor Seating | W/D, Close to Beach & Village Shops

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

10.0 out of 10, Exceptional, (50)
"We loved our stay at Kayla's place! Everything was super clean when we walked in, and she clearly put a lot of thought into stocking up on all the little things you need but might forget to pack. The neighborhood was perfect - easy to get everywhere we wanted to go. Definitely worth booking if you're heading to the area."
The price is SAR 545
SAR 1,285 total
includes taxes & fees
1 Dec - 2 Dec
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Brand-new bay-front home with a private pool and dock

9.2 out of 10, Wonderful, (87)
"The location of the property was fantastic. The house had some issues. The door handle to the balcony was laying on the deck when we arrived. One of the bed frames was broken. The upstairs shower would not shut off completely. Everything was communicated to the property manager by 8 pm the night we arrived. It took several days to get these things resolved. The shower took the longest. It was Wednesday before it was fixed. The house also lacked pots to cook in and a toaster."
Brand-new bay-front home with a private pool and dock

New home 3/2 renovation 3 miles to Siesta Key

8.6 out of 10, Excellent, (4)
"The house was very clean with helpful amenities. However, the only complaint we have would be about the water pressure in the showers. Overall, it was a great experience in a great location, very close to the beach!"
The price is SAR 545
SAR 1,264 total
includes taxes & fees
1 Dec - 2 Dec
New home 3/2 renovation 3 miles to Siesta Key

Oceanfront home w/sunset views of Sarasota Bay

9.8 out of 10, Exceptional, (106)
"This house was perfect to visit our family.it was nice to have all the accommodations of home while being away from home. No problems at all with the home. Kids loved the pool more than the beach. The bay view with a full moon is breathtaking!"
Oceanfront home w/sunset views of Sarasota Bay

2nd-floor duplex near beach with heated pool, grill, balcony, & W/D

9.2 out of 10, Wonderful, (19)
"very nice rental, had a great weekend"
2nd-floor duplex near beach with heated pool, grill, balcony, & W/D

Sarasota-Indian Beach Zen Home (private-pet friendly)

9.8 out of 10, Exceptional, (24)
"We love everything about this property Even our 10 yo said that it’s her fav home "
Sarasota-Indian Beach Zen Home (private-pet friendly)

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

9.8 out of 10, Exceptional, (87)
"We loved our stay! Perfect location to walk to the beach, St. Armand’s circle, and the free trolley that takes you down town. We would stay again! Thank you"
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

Rare! Adorable Cottage on Snead Island, Fish Dock,Tiki & Bch 250 ft. away. Pets

9.8 out of 10, Exceptional, (71)
"Awesome , relaxing quiet getaway "
Rare! Adorable Cottage on Snead Island, Fish Dock,Tiki & Bch 250 ft. away. Pets

2 Bedroom Single Family Home with Pool

9.8 out of 10, Exceptional, (180)
"Loved the pool, great location for what we needed. Excellent communication, great tv channel package. "
2 Bedroom Single Family Home with 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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Other property types in Legacy Trail

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2074)
"Our suite was very clean and the hospitality was wonderful. Would definitely recommend to anyone. If we ever visit the area again we would definitely stay there."
The price is SAR 601
SAR 658 total
includes taxes & fees
1 Dec - 2 Dec
Hibiscus Suites - Gateway to Siesta Key

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (211)
"Facility was great … would certainly stay here again in the future "
The price is SAR 1,391
SAR 1,735 total
includes taxes & fees
3 Dec - 4 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club

Luxury home with Pool, Putting Green, Beach Bikes!

9.6 out of 10, Exceptional, (28)
"Absolutely stunning house! Decor is beautiful, beds are comfortable, porch is amazing, location is great and pool/spa is perfect!! Best house we have ever stayed in! Would recommend to all my family and friends. "
Luxury home with Pool, Putting Green, Beach Bikes!
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.