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Check prices for these dates

Next weekend
26 Sep - 28 Sep
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Vacation Homes in Legacy Trail

Our top choices for Legacy Trail vacation homes

Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | 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. "
The price is SAR 465
SAR 1,081 total
includes taxes & fees
22 Sep - 23 Sep
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, (51)
"House was very nice. Was clean when we arrived. Plenty of space and beautiful view "
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 SAR 2,082
SAR 5,561 total
includes taxes & fees
13 Oct - 14 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, (136)
"Overall stay was good. Location was great. Quick walk to the beach and village. The host, Lisa, did a great job accommodating our stay. "
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 SAR 321
SAR 734 total
includes taxes & fees
19 Sep - 20 Sep
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)
"Directly across from public beach, nice clean pool and the pond was perfect! We really enjoyed our stay! The pond has turtles and crabs that are so much fun to watch right from your porch/balcony! We hope to do this trip yearly!"
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!

10.0 out of 10, Exceptional, (5)
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, (22)
"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, (27)
"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

9.6 out of 10, Exceptional, (65)
"Very comfortable and perfect location to the airport! "
The price is SAR 454
SAR 863 total
includes taxes & fees
19 Oct - 20 Oct
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, (65)
"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 SAR 1,435
SAR 3,219 total
includes taxes & fees
21 Sep - 22 Sep
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!

10.0 out of 10, Exceptional, (1)
"We loved this house. We celebrated a cousins 50th birthday and had so much fun. The location is close to all restaurants and beach. The golf cart was so fun to use. The house is nicely stocked with necessary items, pool noodles and toys. There was everything needed for the beach.The most important part was the owners were very responsive to all questions. We look forward to coming and staying here again."
Sweet "Rae" of Sunshine-Coastal Oasis, Prime location & GOLF CART INCLUDED!
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop

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.
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Top Legacy Trail Hotel Reviews

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Had a wonderful stay I will definitely recommend to others "
Lori 2-night trip
Posted 2 days ago
The Westin Sarasota