Search Vacation Homes in Legacy Trail

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Compare 922 Vacation Homes in Legacy Trail with updated reviews, rates, and availability.

LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

9.6 out of 10, Exceptional, (85)
"Over all great, just never got a response on if the pool was heated or not"
LUXURY HOUSE BY THE CANAL , Pets welcome 😀🐕.

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (223)
"Perfect location to walk to beach and town. The Villas and grounds were well maintained. I wouldnt hesitate staying hefe again."
Tropical Villas of Venice Beach

New home 3/2 renovation 3 miles to Siesta Key

9.2 out of 10, Wonderful, (7)
"This was a really great find. Comfortable beds, close to beach and easy access back to the airport. Only issue was a lot of animal hair was left behind, but easy fix with the vacuum. If we return for vacation we’ll stay again! "
The price is AED 533
AED 1,214 total
includes taxes & fees
18 Mar - 19 Mar
New home 3/2 renovation 3 miles to Siesta Key

Casa Azul 2bed/1bath

9.4 out of 10, Exceptional, (54)
"nice place close to the things we wanted to do..ringling museum,beach,yoders restaurant etc.while the house is located in not the best part of town..it was quiet..and clean..and a very good price"
The price is AED 415
AED 761 total
includes taxes & fees
11 Mar - 12 Mar
Casa Azul 2bed/1bath

Anna Maria Beach Condo 1/1

9.8 out of 10, Exceptional, (164)
"The Condo was in a perfect location. Steps to the beach, steps to the free Trolley which was amazing to use to get around and see all of the Island. Was a perfect location!"
The price is AED 771
AED 1,596 total
includes taxes & fees
18 Mar - 19 Mar
Anna Maria Beach Condo 1/1

Bohemian Sunrise

10.0 out of 10, Exceptional, (77)
"From the beginning of finding/ choosing this place the whole process was so smooth. Laura was always accessible when we had questions. The place and location are both awesome. The house was super clean and nicely decorated. We loved Manasota key and the area. Due to recent hurricanes the beach is under construction, but some restaurants were open. We traveled a bit to ride bikes and at the end of each day/ night, this place was great to go “home “ to. We will most definitely stay again!!!"
Bohemian Sunrise

Private Heated Pool House 6 miles from the Beach

9.8 out of 10, Exceptional, (219)
"Every step for rental went flawlessly. From check-in to condition of property to eminities. Everything was top notch and I would highly recommend this rental. "
Private Heated Pool House 6 miles from the Beach

Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

8.8 out of 10, Excellent, (5)
"We stayed 2 nights and everything was good. I was Leary booking a vacation from a hotel name for a small condo/ hotel room. This room had 2 queen beds, bathroom and all amenities as a hotel for half the price. Thank you … would recommend this for others that don’t need a high end place. Thanks again"
The price is AED 312
AED 634 total
includes taxes & fees
23 Mar - 24 Mar
Ramada Sarasota Waterfront and Marina Community with Tikki Bar and Grill

Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

9.6 out of 10, Exceptional, (114)
"Everything was as expected with the property - however, there was no communication about the cleanup and construction going on all around - I know it was out of your control with the hurricane damage, but I would say that we overpayed for the condition of the area.Lisa did a very good job with communication and the checkin process - Thanks "
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"

Cozy Cottage - Steps to Riverwalk/Close to Beaches

10.0 out of 10, Exceptional, (160)
"We stayed for a quick weekend, in town for a wedding. The property is BETTER and more spacious than pictures make it seem. Very clean and well stocked for our stay! Great location. Thanks again!"
Cozy Cottage - Steps to Riverwalk/Close to Beaches

BRAND NEW EVERYTHING!!!!! 4 bedrooms and sleeps 10 easily.

10.0 out of 10, Exceptional, (14)
"We loved this home. Newly renovated and spacious. We especially liked that half of the house can be closed off for our visiting guest. We would definitely stay here again. "
BRAND NEW EVERYTHING!!!!! 4 bedrooms and sleeps 10 easily.

Private pool House with Fountains & Beach Walkable

9.6 out of 10, Exceptional, (167)
"I have stayed at several VRBO's and this house was the cleanest we've ever stayed at! Immaculate was the word I used to my family who live near this property. Everything is updated and had every amenity you could want. I will be staying at this property for all my future visits. Thank you Amy and team!!!"
Private pool House with Fountains & Beach Walkable

Updated home with enclosed pool, open layout, grill, W/D, streaming, and AC

10.0 out of 10, Exceptional, (11)
"Excellent home in great neighborhood! Perfect for our weekend escape from New England’s winter weather. Enjoyed coffee in the sunroom overlooking the pool and palm trees. Comfy, cozy and cant wait to return."
Updated home with enclosed pool, open layout, grill, W/D, streaming, and AC

Walk-up suite with on-site pool, private deck, full kitchen - walk to beach

9.0 out of 10, Wonderful, (8)
"Perfect spot within walking distance to Bridge Street. Definitely will stay here again!"
Walk-up suite with on-site pool, private deck, full kitchen - walk to 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

Little Charm-Close to AMI, IMG and GT Bray Park.

9.8 out of 10, Exceptional, (7)
"Quick visit to see family. Location was close to campus and was great for our needs. Thank you for having a great venue in a good location."
The price is AED 514
AED 1,171 total
includes taxes & fees
3 Mar - 4 Mar
Little Charm-Close to AMI, IMG and GT Bray Park.

Beachside Retreat with Pool and Beach Access

9.0 out of 10, Wonderful, (33)
"See above "
The price is AED 2,836
AED 5,109 total
includes taxes & fees
22 Feb - 23 Feb
Beachside Retreat with Pool and Beach Access

The Pink House Unit A: A Cozy Retreat Steps from the Beach

9.4 out of 10, Exceptional, (64)
"We had a great time in AMI staying at this charming little pink house just across a bit from beach access. We had plenty of room."
The Pink House Unit A: A Cozy Retreat Steps from the Beach

Cozy house near Siesta Key Beach

10.0 out of 10, Exceptional, (9)
"Clean, updated. Great fenced in yard for the dog. Convenient location right off Tamiami."
Cozy house near Siesta Key Beach

Charming Private Garden Cottage hide away in the heart of Sarasota

10.0 out of 10, Exceptional, (149)
"We enjoyed our stay here and hopefully we will be back. It is just like the pictures. The owners were great! Thank you for letting us stay at your property!"
Charming Private Garden Cottage hide away in the heart of Sarasota
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.
Don't see what you're looking for?
See all available properties in Legacy Trail
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Legacy Trail

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4560)
"Perfect location! "
The price is AED 940
AED 1,145 total
includes taxes & fees
24 Feb - 25 Feb
Tropical Beach Resorts

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (188)
"All stay was friendly, very clean. Rooms cleaned daily. Would rate 5 "
The price is AED 2,596
AED 3,286 total
includes taxes & fees
22 Feb - 23 Feb
Anna Maria Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (217)
"Nice little spot close to Siesta Key Beach.Even has an outdoor stage.I like entertaining and it looks like a perfect place to practice.i really did not mind being in the Tiny House it kind of felt like a Hollywood prop.Anyway this is Hollywood and you are in my world.Love is everything."
The price is AED 470
AED 739 total
includes taxes & fees
10 Mar - 11 Mar
Tiny House Siesta
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.