Legacy Trail Holiday Rentals

  • 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
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Legacy Trail

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
The price is AU$331
includes taxes & fees
9 Jan - 10 Jan
Tropical Beach Resorts
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sports facility

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (220)
"Very lovely (and large!) accommodation. Extremely clean. Front desk staff kind of rude/pretentious.Great location right on the beach at Siesta Key. Heated pool with good poolside bar. Also had a hot tub, which was nice as the weather was a bit cool when we were there. Feel like I was misled a bit based on room description--thought we were booking a room with beach view, but instead got "city view"--which essentially looked into a back alley and at a 7-eleven. For the price/my personal budget,...
The price is AU$1,002
includes taxes & fees
22 Jan - 23 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2081)
"Would stay again"
The price is AU$318
includes taxes & fees
6 Jan - 7 Jan
Hibiscus Suites - Gateway to Siesta Key
Luxury home with Pool, Putting Green, Beach Bikes!
A heated pool

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!
Anna Maria Beach Resort
On the beach, white sand, beach towels

Anna Maria Beach Resort

3.5 star property
9.4 out of 10, Exceptional, (179)
"Love the place, near a beautiful beach, staff friendly and accommodating, best beds and linens ever! I did not want to leave! Thank you! "
The price is AU$781
includes taxes & fees
16 Jan - 17 Jan
Anna Maria Beach Resort
Captiva Beach Resort
Florida Family Single | Private kitchen

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1062)
"Amazing!!! What can I say, considering this place got hit hard after the hurricane 2 months ago, the clear up and refurbishment is incredible. With just a 2 min stroll to one of the best beaches and some great restaurants, I would definitely recommend this property. In particular, Jen at reception was fab xx"
The price is AU$433
includes taxes & fees
6 Jan - 7 Jan
Captiva Beach Resort
Tiny House Siesta
Cabin (Tiny House - Yellow Lifeguard Stand) | Living area

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (189)
"Beautiful place to stay with family my kids love very close to the beach Siesta Beach EVERYTHING ESPERTACULARRRRRRR."
The price is AU$324
includes taxes & fees
6 Jan - 7 Jan
Tiny House Siesta
The Ringling Beach House
Aerial view

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (285)
"This was a lovely place. Just loved it. Will be back. "
The Ringling Beach House
Anna Maria Sunsets - studio
Sun-loungers, beach towels

Anna Maria Sunsets - studio

9.4 out of 10, Exceptional, (205)
"Perfect stay for couples. Small but beautiful. It was super easy to talk with owner. Just across from beach. "
The price is AU$382
includes taxes & fees
6 Jan - 7 Jan
Anna Maria Sunsets - studio
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (301)
"I love that this property is right on the beach. We were there over Christmas. The property was not fully booked, so it was fairly quiet. The Gulf was too cold for us, but we enjoyed using the the provided lounge chairs to relax on the beach. Lots of shelling to do. Not a lot of people at this time. Pool was not a bad temperature and was clean. The property looks like an old motor lodge, but they have kept it nice. Our room did not have a lot of updates, but it was sufficient. A roll of paper...
Sea Club I Beach Resort
Haley's at The Anna Maria Island Inn
Beach nearby, white sand, sun-loungers, beach towels

Haley's at The Anna Maria Island Inn

3.0 star property
8.6 out of 10, Excellent, (369)
"The bed in our room was extremely comfortable."
Haley's at The Anna Maria Island Inn
Pelican Post at Anna Maria Island Inn
Garden

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (261)
"Beautiful boutique resort. Clean rooms, great pool and hot tub. Walking distance around Anna Maria Island. Parking included. I highly recommend :)"
Pelican Post at Anna Maria Island Inn
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
On the beach

SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B

8.6 out of 10, Excellent, (33)
"We were there when hurricane Debbie hit. Took down the fence and air conditioners. The owner was there within 30 minutes to have everything fixed. Other than that this is our happy place. We will be bsck"
SIESTA KEY 100 FEET FROM THE BEACH! TROPICAL GREEN UNIT B
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (170)
"Owners we're everything you would want tthem to be."
The price is AU$572
includes taxes & fees
6 Jan - 7 Jan
Kon Tiki Inn
SEPT OCT NOV DISCOUNTS! AMI White Sand Beaches/IMG ACADEMY/Pickle Ball/GOLF/FUN!
Miscellaneous

SEPT OCT NOV DISCOUNTS! AMI White Sand Beaches/IMG ACADEMY/Pickle Ball/GOLF/FUN!

10.0 out of 10, Exceptional, (13)
"Great long weekend stay while my daughter had a lacrosse tournament at IMG! Super convenient, extremely comfortable and a great option for families! Wish we were there for a longer stay :-)"
The price is AU$1,067
includes taxes & fees
12 Jan - 13 Jan
SEPT OCT NOV DISCOUNTS! AMI White Sand Beaches/IMG ACADEMY/Pickle Ball/GOLF/FUN!
The Sailor Park
Exterior

The Sailor Park

3.0 star property
3.0 out of 10, (20)
"This was a very welcome get away. Absolutely beautiful views. The owner is great. I definitely will come back. "
The Sailor Park
The Pink House Unit B: A Cozy Retreat Steps from the Beach
Iron/ironing board, WiFi, bed sheets

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

9.8 out of 10, Exceptional, (79)
"This is a great property for one person or a couple. It is such a cute apartment in a great location."
The Pink House Unit B: A Cozy Retreat Steps from the Beach
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Beach nearby, sun-loungers, beach towels

Vacation delight! Cozy condo just steps from the beach and St. Armands circle.

10.0 out of 10, Exceptional, (127)
"Sue worked very hard on restoring this property after the hurricanes. It was beautiful on the inside. It was very spacous with all new furnishings. The location is within walking distance to the beach, food, drinks, and shopping. The only downside was having to leave. We cannot recommend this place enough."
Vacation delight! Cozy condo just steps from the beach and St. Armands circle.
Palm Tree Villas
Outdoor pool, pool umbrellas, pool loungers

Palm Tree Villas

3.0 star property
9.2 out of 10, Wonderful, (159)
"Our studio villa was perfect for our stay. Very clean, loved the outdoor patio! Pool is heated, nice and relaxing. Having a beach wagon with umbrella and chairs was an added bonus. The villas location is excellent. short walk to the beach, restaurants and stores very close by."
The price is AU$558
includes taxes & fees
9 Jan - 10 Jan
Palm Tree Villas
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
Outdoor pool, a heated pool

Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!

9.2 out of 10, Wonderful, (41)
"We arrived early and weren't able to check in early but the Ramada Inn staff were very accommodating. Offered us access to the pool and restaurant while we waited until the 4pm check in time. The food was great and and the staff were awesome! The only thing I wish I'd known was you can't fish from their docks."
The price is AU$409
includes taxes & fees
10 Jan - 11 Jan
Waterfront Unit, Heated Pool, 70" TV, Tiki Bar & Grill, On The Marina!
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
Sign in
Sign up, it's free

Other types of properties in Legacy Trail you may be interested in

Hyatt Regency Sarasota
Outdoor pool, pool loungers

Hyatt Regency Sarasota

4.0 star property
8.2 out of 10, Very good, (1008)
"Great"
The price is AU$393
includes taxes & fees
2 Feb - 3 Feb
Hyatt Regency Sarasota
Golden Host Resort - Sarasota
Bar (on property)

Golden Host Resort - Sarasota

3.0 star property
8.4 out of 10, Very good, (1629)
"I was traveling with my son for a sporting event. The room was clean and comfortable. The property was nice and felt safe. The pool area was very pleasant to sit in. The staff were friendly and helpful. I would stay there again with the family."
The price is AU$181
includes taxes & fees
6 Jan - 7 Jan
Golden Host Resort - Sarasota
Kompose Boutique Hotel
Lobby sitting area

Kompose Boutique Hotel

3.0 star property
9.0 out of 10, Wonderful, (3613)
"Nice hotel. I left a review on Google"
The price is AU$256
includes taxes & fees
7 Jan - 8 Jan
Kompose Boutique Hotel
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.