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Compare 43 Villas in Legacy Trail with updated reviews, rates, and availability.

Beach, Sand, Sunsets. . . Rocking chair in front of the porch!

10.0 out of 10, Exceptional, (102)
"So it was immediately after Hurricane Helene. Pat kept us updated as we were on the road to the property. The day before we were to arrive Pat called and said option A was out and option B would have too much water. So she refunded all our money including the VRBO fee. Excellent and honest host."
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!

180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow

9.6 out of 10, Exceptional, (89)
"The property is just as described! It was incredible. The beach and stores were all walking distance. Definitely would stay there again."
The price is SAR 1,540
SAR 3,624 total
includes taxes & fees
2 Dec - 3 Dec
180-degree water views! Shared pool and laundry - Bay Vista at Bayside Bungalow

Venice Island / Venice Beach Luxury Villa

9.4 out of 10, Exceptional, (106)
"Everything was excellent, but the windows and patio doors need need to be cleaned."
Venice Island / Venice Beach Luxury Villa

Ground Floor Luxury Villa Steps From Venice Beach

9.2 out of 10, Wonderful, (95)
"One block away from the beach!!!! Had a minor issue with the property, called the property Manager , very friendly , and she took care of the situation immediately. Walking distance to restaurants, shopping, and fun events. Excellent visit!!!"
Ground Floor Luxury Villa Steps From Venice Beach

Renovated 1 Bed / 1 Bath Condo on Siesta Beach!

10.0 out of 10, Exceptional, (6)
"This place exceeded our expectations! Everything was clean and the furniture was comfortable. The kitchen is perfect with the appliances and the washer dryer a huge plus! The location to the beach and other fun things to do! Communication was great, check in and check out was super easy! Hopefully we will be back again!!"
Renovated 1 Bed / 1 Bath Condo on Siesta Beach!

Vacay in luxury! So close to the beach!

9.6 out of 10, Exceptional, (54)
"An absolutely beautiful stay. The room was cute and quiet. I would recommend by far. "
Vacay in luxury! So close to the beach!

Shared Pool, Bay Views! - Barefoot by the Bay at Bayside Bungalow

9.8 out of 10, Exceptional, (35)
"Location was great, right off Pine and very near great restaurants, ice cream, shops, pier and small Bay beach. Direct shot down to the bigger beach and easy to find street parking. Very clean, great space, unique layout but kids had no problem sleeping on the trendle and sleeper couch."
Shared Pool, Bay Views! - Barefoot by the Bay at Bayside Bungalow

Waterfront Villa Seaglass

10.0 out of 10, Exceptional, (73)
"Villa is very nice. Great location with beautiful view of Lemon Bay. Very quiet and relaxing. We will be back. "
Waterfront Villa Seaglass

Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.

9.8 out of 10, Exceptional, (84)
"Lisa is great to rent from "
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.

Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level

10.0 out of 10, Exceptional, (90)
"We love this house especially the pool. My kids enjoy most of the time before and after the a day at the beach. It’s very warm and also refreshing. Perfect size for big kids who like to swim and dive deep and sallow part for a baby to enjoy the water as well. The house had fully load kitchen equipment and fully stocked, very clean and functional, plenty of beach towel, extras bed sheet’s ,pillows. perfect for a family of five, less then 2 block from the beach, well maintain pool and ground...
Palm Oasis East Villa, Shared Heated Salt Pool, Steps to the Beach, Ground Level

Direct Beachfront Gulf with Amazing Views

9.8 out of 10, Exceptional, (89)
"What a fantastic spot. The beach was terrific… the condo had every amenity we needed…. The pool was lovely. Dolphins and manatees in the water… close to restaurants and shopping. Beautiful sunsets and storm watching. We are so sad to be leaving because we had such an amazing vacation. I can’t think of a single thing we would have done differently. Thank you!!!"
Direct Beachfront Gulf with Amazing Views

Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill

9.8 out of 10, Exceptional, (124)
"Property was so handy to the beach. We had a few quirks when we first arrived which were immediately remedied. We appreciate the great service! "
Steps to the Beach with Shared Heated Salt Pool and Private Backyard & Grill

Gorgeous Villa at Islands West Resort! Shared pool, close to beach!

9.8 out of 10, Exceptional, (57)
"The unit we stayed at was perfect for our little family of 3. The walk to the beach was only about 2-3 mins. The only thing that would have been better was if the unit had extra chairs or even offered an umbrella. The pool would have been better if it was cleaned daily rather than just 2 days a week. We did someone come by but they only tested the water, they did not clean it. My spouse cleaned it everyday when we used it. There was plenty of room outside and enough lounge chairs. Overall we...
Gorgeous Villa at Islands West Resort! Shared pool, close to beach!

Paradise with a pool, pier and private beach area

9.0 out of 10, Wonderful, (18)
"The location of this house is spectacular! Beautiful view of the Intercostal ! I was so excited to share this house with friends and family. There were several things that were not what I would have expected to encounter in a home of this stature. There were at least 3 chairs and a sofa that were badly soiled. Drawers in the kitchen were dirty with someone else’s crumbs. I have a dog and I know how important it is to pick up after her but upon my arrival, I was checking things out and noticed...
Paradise with a pool, pier and private beach area

Embrace Island Living at Villa #8 AMI Lemon Fish – Steps from the Gulf Beach!

9.4 out of 10, Exceptional, (31)
"Enjoyed our stay in the cottage. Met some friendly people and definitely will return."
Embrace Island Living at Villa #8 AMI Lemon Fish – Steps from the Gulf Beach!

Bayside Cutie at Bayside Bungalow: Anna Maria Island Getaway Near Pine Avenue!

9.2 out of 10, Wonderful, (59)
"This place is very small. I would not stay here again with more than one other person. Bathroom is the smallest I have ever seen. No where to put your wet towels or swimsuits. Pool was almost never at the correct temperature. They came to fix it but I had to tell them every day. Overall a lot of money for not a lot of amenities."
Bayside Cutie at Bayside Bungalow: Anna Maria Island Getaway Near Pine Avenue!

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (52)
"All was great. Only want to point out that the door leading into bathroom was stuck and appears to be water damaged or rotted in the bottom. Also could not turn on the main light by living room/kitchen area. Not complaining, just thought you should know. "
Waterfront Mermaid's Retreat Delights!

⚓Sea Site Retreat Unit B! Great attractions nearby! Short walk to the beach!⚓

9.2 out of 10, Wonderful, (27)
"House was so cute! Very clean and easy instructions. Would rent this house again!"
⚓Sea Site Retreat Unit B! Great attractions nearby! Short walk to the beach!⚓

Starfish East- Beautiful Villa private pool and a few steps to the beach

10.0 out of 10, Exceptional, (68)
"This property and pool were beautiful and clean. It was 1 min from the beach and down the road from Bridge St pier, which made it great for teens. We really appreciated the beach chairs, umbrella, beach cart and beach tent. The only change I would recommend would be to have a garbage disposal installed. "
Starfish East- Beautiful Villa private pool and a few steps to the beach

Casa Blanca Villa D08

9.4 out of 10, Exceptional, (16)
"Everything were perfect"
Casa Blanca Villa D08
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.