A wooden pathway surrounded by dense greenery and trees.

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Legacy Trail vacation homes

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

1. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is ￥18,140
￥54,085 total
includes taxes & fees
Sep 7 - Sep 8
Siesta Key Island Rentals
A wooden pathway leading to a beach with clear turquoise water and a wooden railing on one side.

2. Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (268 reviews)
"It was amazing and way beyond what I thought. Easy walk to beach(0.4 mikes) and shops. Private location with small pool. Just what you need."
United States
Christina
The price is ￥15,061
￥17,019 total
includes taxes & fees
Sep 1 - Sep 2
Tropical Villas of Venice Beach
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

3. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (33 reviews)
"We appreciated the excellent location and good service. However, the listing should provide clearer and more accurate information about the layout, especially that the only bathroom is located inside one of the bedrooms. This arrangement significantly reduces privacy and makes the two-bedroom setup less convenient than expected. The additional $40-per-person bicycle fee should also be clearly stated in the listing."
United States
Tatyana
The price is ￥11,542
￥44,410 total
includes taxes & fees
Sep 1 - Sep 2
[escape to paradise] siesta key beach getaway
A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

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

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (84 reviews)
"Her stay was outstanding everything was so professionally ready for us we felt at home comfortable the Privacy was impeccable"
United States
James W.
The price is ￥11,671
￥40,442 total
includes taxes & fees
Sep 7 - Sep 8
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
A modern kitchen with white cabinets, a dining area with a dark wooden table set for four, and a chandelier.

5. Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
Sarasota Springs
10.0 out of 10, Exceptional, (13 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is ￥13,688
￥53,634 total
includes taxes & fees
Sep 1 - Sep 2
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly
A wooden deck with white railings, red chairs, and a view of a residential area with palm trees and a blue house.

6. Island Villa | Cozy Beach Retreat | Walk to Village

Island Villa | Cozy Beach Retreat | Walk to Village
Siesta Key Village
8.4 out of 10, Very Good, (14 reviews)
"Great place to stay and very close to restaurants "
United States
Amber B.
The price is ￥14,728
￥60,655 total
includes taxes & fees
Sep 1 - Sep 2
Island Villa | Cozy Beach Retreat | Walk to Village
A modern kitchen with white cabinets, a stainless steel microwave, an oven, and a coffee maker.

7. Charming 2-bedroom house in lovely Sarasota with yard.

Charming 2-bedroom house in lovely Sarasota with yard.
Kensington Park
9.2 out of 10, Wonderful, (34 reviews)
"My husband and I really enjoyed our stay at this home. It was clean, nicely decorated, and had everything we needed. The host was very responsive and friendly. The neighborhood was quiet and nice. The AC works well."
United States
Julie B.
The price is ￥16,569
￥37,518 total
includes taxes & fees
Sep 1 - Sep 2
Charming 2-bedroom house in lovely Sarasota with yard.
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

8. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (218 reviews)
"The host was very communicative and responsive. The pool was a big hit for our family. Comfy beds and a convenient drive to the beach and other venues. Would definitely stay here again. "
United States
Jennifer M.
The price is ￥19,451
￥74,786 total
includes taxes & fees
Sep 8 - Sep 9
Siesta beach....one and only
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

9. Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
The price is ￥16,569
￥57,792 total
includes taxes & fees
Sep 7 - Sep 8
Dolphin Villa - Pool - Steps to Siesta Key Village
A wooden deck with blue lounge chairs, orange chairs, and a barbecue area.

10. Everglades Villa • Sleeps 8 • Walk to Siesta Beach

Everglades Villa • Sleeps 8 • Walk to Siesta Beach
Siesta Key Village
9.0 out of 10, Wonderful, (15 reviews)
"We loved staying here for my bachelorette!"
United States
Kelsey E.
The price is ￥20,251
￥68,073 total
includes taxes & fees
Sep 9 - Sep 10
Everglades Villa • Sleeps 8 • Walk to Siesta Beach
A modern kitchen with white cabinets, a stainless steel refrigerator, and a large island with bar stools.

11. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
The price is ￥11,378
￥44,204 total
includes taxes & fees
Sep 7 - Sep 8
[lounge like locals] walk to siesta beach +bikes
A modern kitchen with a central island, bar stools, a window, and a dark cabinet.

12. Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (27 reviews)
"The perfect place and the best rental I’ve stayed in!! All the descriptions are perfect. If you’re looking for a private getaway that’s close and cozy, this is it."
United States
Emma
The price is ￥13,403
￥37,557 total
includes taxes & fees
Sep 1 - Sep 2
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
A modern kitchen with white cabinetry, stainless steel appliances, and a tiled backsplash.

13. Condo with Private Beach Access, Great Shared Amenities - Private Beach House

Condo with Private Beach Access, Great Shared Amenities - Private Beach House
Siesta Key
9.2 out of 10, Wonderful, (49 reviews)
"Perfect spot for beach vacation "
United States
Megan C.
The price is ￥35,037
￥141,679 total
includes taxes & fees
Sep 1 - Sep 2
Condo with Private Beach Access, Great Shared Amenities - Private Beach House
A beach with clear turquoise waters, a sandy shore, and scattered umbrellas.

14. Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
Nokomis
10.0 out of 10, Exceptional, (46 reviews)
"Great spot close to many attractions. Very well appointed with all that you need for a great vacation!"
United States
Suzanne G.
The price is ￥29,490
￥70,535 total
includes taxes & fees
Sep 1 - Sep 2
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille
A covered porch with a door, a small table with a potted plant, and a window with blinds.

15. Venice Dove Shell

Venice Dove Shell
Venice East
9.8 out of 10, Exceptional, (9 reviews)
"Great place!!"
United States
Scot
The price is ￥20,812
￥57,056 total
includes taxes & fees
Sep 1 - Sep 2
Venice Dove Shell
A beachside restaurant with a thatched roof, wooden tables, and chairs, overlooking a sandy beach and the ocean.

16. LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access

LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
Sunny Shores
9.6 out of 10, Exceptional, (44 reviews)
"Superb value, quiet area, responsive owner, very nicely appointed; will definitely book again for next visit to Anna Maria Island!"
United States
Bryce W.
The price is ￥14,248
￥78,332 total
includes taxes & fees
Sep 1 - Sep 2
LAST MINUTE DEAL, Charming Elevated Duplex – Relaxing Beach Getaway Near Anna Maria Island- Bay access
A two-story house with a covered porch, a small front yard, and a clear blue sky.

17. The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (177 reviews)
"Great downtown location! We enjoyed our stay!"
United States
Diane M.
The price is ￥17,450
￥48,434 total
includes taxes & fees
Sep 1 - Sep 2
The Hideaways at Point Pleasant (Palm Side)
A beach with clear turquoise water, white sand, and a row of trees and buildings along the shore.

18. IMG Lake & Beach Home Pool White Sand Beaches Aug, Sept, Oct, Nov, Dec SPECIALS!

IMG Lake & Beach Home Pool White Sand Beaches Aug, Sept, Oct, Nov, Dec SPECIALS!
South Bradenton
9.8 out of 10, Exceptional, (140 reviews)
"Beautiful pool, nice kitchen, and close to Anna Marie Island."
United States
Gary B.
The price is ￥18,410
￥84,423 total
includes taxes & fees
Sep 1 - Sep 2
IMG Lake & Beach Home Pool White Sand Beaches Aug, Sept, Oct, Nov, Dec SPECIALS!
A beach with a sunset and ocean.

19. Villa Paradiso - Private Saltwater Pool - 5 Min to Siesta Key

Villa Paradiso - Private Saltwater Pool - 5 Min to Siesta Key
Sarasota
10.0 out of 10, Exceptional, (82 reviews)
"Very nice place and the neighborhood very quiet"
United States
Ieshia M.
The price is ￥43,224
￥105,915 total
includes taxes & fees
Sep 1 - Sep 2
Villa Paradiso - Private Saltwater Pool - 5 Min to Siesta Key
A compact, stainless steel LG ThinQ washer and dryer unit in a small, enclosed laundry room with a white door and light-colored walls.

20. Cozy Studio in Quiet Neighborhood

Cozy Studio in Quiet Neighborhood
Bradenton
9.0 out of 10, Wonderful, (14 reviews)
"Very clean and wonderful area"
United States
Jared B.
The price is ￥9,285
￥26,357 total
includes taxes & fees
Sep 6 - Sep 7
Cozy Studio in Quiet Neighborhood
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

Find out more about Legacy Trail

Legacy Trail Vacation Homes information

Number of reviews
1,032
Accommodation
0 Vacation Homes
Lowest Price
￥17,019
Highest Price
￥141,679

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