A wooden pathway surrounded by dense greenery and trees.

Holiday Homes in Legacy Trail

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Our top choices for Legacy Trail holiday homes

1. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (45 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is NZ$521
includes taxes & fees
13 Sept - 14 Sept
Siesta Heron Suites & Villas

2. 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 NZ$428
includes taxes & fees
14 Sept - 15 Sept
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

3. 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 NZ$640
includes taxes & fees
11 Sept - 12 Sept
Dolphin Villa - Pool - Steps to Siesta Key Village

4. 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, (14 reviews)
"Host is really friendly n helpful!! Loved our stay and would definitely stay again "
United States
Kathryn K.
The price is NZ$565
includes taxes & fees
12 Sept - 13 Sept
Sunny 3BR Oasis • Water View • 2 TVs • Beach Gear • Fenced Yard • Pet Friendly

5. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Easy process in and out. Would definitely do business with them again. A"
United States
Derek J.
The price is NZ$514
includes taxes & fees
13 Sept - 14 Sept
[escape to paradise] siesta key beach getaway

6. 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 NZ$794
includes taxes & fees
17 Sept - 18 Sept
Siesta beach....one and only

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 NZ$397
includes taxes & fees
11 Sept - 12 Sept
Charming 2-bedroom house in lovely Sarasota with yard.

8. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (20 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
The price is NZ$421
includes taxes & fees
12 Sept - 13 Sept
The Dolphin

9. Luxury Family Home Near Downtown & Siesta Key Beach

Luxury Family Home Near Downtown & Siesta Key Beach
Alta Vista
9.8 out of 10, Exceptional, (80 reviews)
"Excellent property at a great value. Very clean and centrally located. "
United States
Joseph C.
The price is NZ$593
includes taxes & fees
14 Sept - 15 Sept
Luxury Family Home Near Downtown & Siesta Key Beach

10. Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals
South Village
9.6 out of 10, Exceptional, (72 reviews)
"It was very clean and close to the beach. Perfect location."
United States
Cortney
The price is NZ$1,019
includes taxes & fees
11 Sept - 12 Sept
Star Fish. 3 Bed 2 Bath. POOL. Daily Rentals

11. 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 NZ$418
includes taxes & fees
15 Sept - 16 Sept
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

12. Gulf Villa - 3 min to #1 Beach - Pool

Gulf Villa - 3 min to #1 Beach - Pool
Siesta Key Village
9.0 out of 10, Wonderful, (17 reviews)
"Nice place to stay."
United States
Ruben C.
The price is NZ$724
includes taxes & fees
14 Sept - 15 Sept
Gulf Villa - 3 min to #1 Beach - Pool

13. 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 NZ$724
includes taxes & fees
14 Sept - 15 Sept
Everglades Villa • Sleeps 8 • Walk to Siesta Beach

14. Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Siesta Key
9.6 out of 10, Exceptional, (68 reviews)
"We enjoyed the space this property offered our party of 6. We also appreciated the beach side location and proximity to restaurants and shops. We would stay here again."
United States
Meredith S.
The price is NZ$1,016
includes taxes & fees
11 Sept - 12 Sept
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND

15. Venice Dove Shell

Venice Dove Shell
Venice East
9.8 out of 10, Exceptional, (10 reviews)
"Great place!!"
United States
Scot
The price is NZ$597
includes taxes & fees
11 Sept - 12 Sept
Venice Dove Shell

16. 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, (50 reviews)
"Perfect spot for beach vacation "
United States
Megan C.
The price is NZ$1,486
includes taxes & fees
11 Sept - 12 Sept
Condo with Private Beach Access, Great Shared Amenities - Private Beach House

17. Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA
Bradenton
10.0 out of 10, Exceptional, (14 reviews)
"Great spot, lovely back yard and pool, so relaxing we loved it."
United States
Cadence
The price is NZ$657
includes taxes & fees
29 Sept - 30 Sept
Waterfront Cottage • Pool • Putting Green • PingPong •Near AMI Beaches • 2BR/2BA

18. 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.
Walk to Beach. Beautifully Renovated 3BR, 2BA Home w/Outdoor Shower & Grille

19. Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Englewood South
10.0 out of 10, Exceptional, (5 reviews)
"Cute, clean, comfortable beds. Perfect for our needs."
United States
Sharon K.
The price is NZ$417
includes taxes & fees
11 Sept - 12 Sept
Charming 2-bedroom house in Englewood with WiFi and AC

20. Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is NZ$379
includes taxes & fees
13 Sept - 14 Sept
Nestled in North Port. Updated 2 Bed / 1 Bath.
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 Holiday Homes information

Number of reviews
745
Accommodation
0 Holiday Homes
Lowest Price
NZ$379
Highest Price
NZ$1,486

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