Search Vacation Homes in Legacy Trail

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov
Siesta Key Island Rentals
Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
Siesta Key Island Rentals
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
On the beach, sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (52)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
The price is HK$3,096
HK$7,087 total
includes taxes & fees
29 Sept - 30 Sept
Luxury Siesta Key Beachfront Oasis-STEPS TO WORLD FAMOUS SIESTA KEY SAND
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Beach nearby, sun-loungers, beach towels

Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach

9.8 out of 10, Exceptional, (111)
"Great location and close to beach"
Entire Standalone Lido Beach Villa, 1.2k sf, 1 block to the beach
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT
Outdoor pool, a heated pool

Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT

10.0 out of 10, Exceptional, (1)
"The house is beautiful!! Plenty of room for a family, and plenty to do!The owner was readily available through messages and the phone if we had any questions. It was an easy process, and an excellent experience!!!I highly recommend this house if you just feel like hanging out, or exploring Anna Maria, it’s a beautiful location!!And don’t forget to go down the slide!! "
The price is HK$4,318
HK$11,680 total
includes taxes & fees
15 Oct - 16 Oct
Tortuga Bay~Canal & Waterslide Putt Putt! KAYAKS & TIKI HUT
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Beach nearby, sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (137)
"The home was cozy. Best feature- so close to the beach! "
Siesta Key- 2 Bed 1Bath Villa,1500 ft from Beach, Barefoot Bungalows -"GULL"
Charming 2-bedroom house in lovely Sarasota with yard.
Microwave, oven, stovetop

Charming 2-bedroom house in lovely Sarasota with yard.

10.0 out of 10, Exceptional, (1)
"Easy to check in, clean and comfortable "
The price is HK$665
HK$1,530 total
includes taxes & fees
29 Sept - 30 Sept
Charming 2-bedroom house in lovely Sarasota with yard.
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen
On the beach, sun-loungers, beach towels

Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen

10.0 out of 10, Exceptional, (122)
"I booked this property for a girl’s trip and did was WONDERFUL! It was nice, clean, and very convenient to the beach. The host was very friendly and she responded quickly to my messages. I will definitely stay here again when we return to the area. "
Siesta Key Townhome across from Pristine Sand & Blue Waters 2b/2b king queen
Private Home Directly on Siesta Key Beach!
On the beach

Private Home Directly on Siesta Key Beach!

9.8 out of 10, Exceptional, (6)
Private Home Directly on Siesta Key Beach!
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
On the beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (23)
"Everything is super clean and super good. The beach is super nice. The atmosphere is incredible."
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool
SUGAR REEF "B" One Minute Walk to the Beach!
Beach nearby, sun-loungers, beach towels

SUGAR REEF "B" One Minute Walk to the Beach!

10.0 out of 10, Exceptional, (134)
"The beach is just a block away and it is one of the best sections of this island!"
SUGAR REEF "B" One Minute Walk to the Beach!
NEW Luxury Getaway Near IMG! Pool, Game Room, Beaches – Limited-Time Offers!
Sun-loungers, beach towels

NEW Luxury Getaway Near IMG! Pool, Game Room, Beaches – Limited-Time Offers!

9.8 out of 10, Exceptional, (30)
"Place was very cleanWell equippedClose to several beaches"
NEW Luxury Getaway Near IMG! Pool, Game Room, Beaches – Limited-Time Offers!
Casa Azul 2Bed/1Bath
Terrace/patio

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (66)
"Very comfortable and perfect location to the airport! "
The price is HK$700
HK$1,526 total
includes taxes & fees
29 Sept - 30 Sept
Casa Azul 2Bed/1Bath
Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
Outdoor pool, a heated pool

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village

Siesta Key Oasis-Spectacular with heated pool/spa and steps to beach and Village
Dogs and cats friendly renovated duplex 5 min drive from the beach
Sun-loungers, beach towels

Dogs and cats friendly renovated duplex 5 min drive from the beach

10.0 out of 10, Exceptional, (66)
"Nice clean place to stay"
Dogs and cats friendly renovated duplex 5 min drive from the beach
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Exterior

SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog

9.6 out of 10, Exceptional, (186)
"Bay view was nice "
The price is HK$2,276
HK$5,800 total
includes taxes & fees
2 Oct - 3 Oct
SEPT,-OCT. SPECIALS, BEACHFRONT, PRIVATE BEACH ON THE WATERFRONT, Bring your dog
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
Outdoor pool, a heated pool

Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!

9.6 out of 10, Exceptional, (5)
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
Siesta Heron Suites & Villas
Private kitchen

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas
2 BR 2 Full BA on Anna Maria Island just steps to Beach!
Beach nearby, sun-loungers, beach towels

2 BR 2 Full BA on Anna Maria Island just steps to Beach!

10.0 out of 10, Exceptional, (170)
"Just steps away from the beach, the property has everything you need for the beach, chairs, umbrellas, etc "
2 BR 2 Full BA on Anna Maria Island just steps to Beach!
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
Terrace/patio

Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches

7.8 out of 10, Good, (21)
"Great spit in Venice to bring the dogs and enjoy some early summer vacations "
Updated Large Pool Home w/Game Room W/Pool Table & Darts Only 1/2 Mile Beaches
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Legacy Trail Hotel Reviews

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Clean, comfortable bed and breakfast was excellent "
Michael 1-night trip
Posted 3 days ago
Kompose Boutique Hotel

Find out more about Legacy Trail

Find out more about Legacy Trail

Legacy Trail Vacation Homes information

Number of reviews
1,400
Accommodation
1154 Vacation Homes
Lowest Price
HK$1,526
Highest Price
HK$11,680

Explore a world of travel with Expedia

Explore a world of travel with Expedia