A wooden pathway surrounded by dense greenery and trees.

Legacy Trail Holiday Rentals

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Legacy Trail holiday rentals

Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (289 reviews)
"Great place to stay!!!"
United States
Tara
Kon Tiki Inn
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,274 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is HK$1,293
HK$1,594 total
includes taxes & fees
6 Jul - 7 Jul
Captiva Beach Resort
Beach nearby, white sand, beach towels

Haley's at The Anna Maria Island Inn

Haley's at The Anna Maria Island Inn
3.0 star property
Holmes Beach
8.6 out of 10, Excellent, (461 reviews)
"The property served it's purpose of comfort for relaxation. We enjoyed it thoroughly and will make this an annual trip."
United States
Sydney
The price is HK$1,549
HK$1,960 total
includes taxes & fees
5 Jul - 6 Jul
Haley's at The Anna Maria Island Inn
Beach nearby

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (71 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is HK$776
HK$1,670 total
includes taxes & fees
15 Jul - 16 Jul
The "Grouper"
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,620 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is HK$1,327
HK$1,703 total
includes taxes & fees
2 Aug - 3 Aug
Tropical Beach Resorts
Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (69 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is HK$910
HK$2,676 total
includes taxes & fees
6 Jul - 7 Jul
Siesta Key Island Rentals
Living area

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (370 reviews)
"Loved the tiny house will stay there again!"
United States
Nydia
The price is HK$599
HK$1,630 total
includes taxes & fees
15 Jul - 16 Jul
Tiny House Siesta
Premium bedding, pillow-top beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (644 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is HK$1,520
HK$1,717 total
includes taxes & fees
2 Aug - 3 Aug
A Beach Retreat
Property grounds

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
10.0 out of 10, Exceptional, (68 reviews)
"Excellent stay at Pura Vida——-clean, cool rooms, very relaxing experience on the property. It’s obvious Pura Vida put thought into the arrangement of outside amenities, including couches, dining tables, the spa, and numerous fruit trees planted around the property. Would 100% stay here again."
United States
Alex
The price is HK$699
HK$2,352 total
includes taxes & fees
11 Jul - 12 Jul
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Beach nearby, white sand, beach umbrellas, beach towels

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is HK$3,509
HK$4,400 total
includes taxes & fees
10 Jul - 11 Jul
The Inn On Siesta Key
In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (146 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is HK$2,111
HK$2,385 total
includes taxes & fees
19 Jul - 20 Jul
SeaSpray Resort
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,355 reviews)
"great place to stay for a couple of nights. "
United States
Diana
The price is HK$1,095
HK$1,237 total
includes taxes & fees
2 Aug - 3 Aug
Hibiscus Suites - Gateway to Siesta Key
Beach nearby, sun-loungers, beach towels

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Brad S.
Siesta Key Village-Suite #1: A block to the Beach!
Fridge, microwave, oven, stovetop

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (35 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is HK$1,075
HK$2,898 total
includes taxes & fees
5 Jul - 6 Jul
[lounge like locals] walk to siesta beach +bikes
Outdoor pool, pool umbrellas, pool loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is HK$1,082
HK$4,908 total
includes taxes & fees
7 Jul - 8 Jul
Cedar Run Resort - Roam Hospitality
Terrace/patio

The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (178 reviews)
"We had a wonderful two day stay and we would select it again when we go to Bradenton. The sounding neighbor is quiet and attractive. The unit was very clean - great kitchen, living room, bedroom and bathroom. "
United States
Edward M.
The price is HK$940
HK$2,448 total
includes taxes & fees
5 Jul - 6 Jul
The Hideaways at Point Pleasant (Pine Side)
Exterior

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn
3.5 star property
Bradenton Beach
9.2 out of 10, Wonderful, (422 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
The price is HK$1,598
HK$2,023 total
includes taxes & fees
5 Jul - 6 Jul
Pelican Post at Anna Maria Island Inn
Beach

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Bradenton Beach
9.6 out of 10, Exceptional, (29 reviews)
"Great location perfect room for 2 people. "
United States
Macey
The price is HK$1,130
HK$2,489 total
includes taxes & fees
13 Jul - 14 Jul
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
On the beach, beach umbrellas

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (80 reviews)
"Very happy with my stay. Room was very clean, beautifully decorated and very comfortable. Perfect efficiency! Highly recommend"
United States
Gloria
The price is HK$1,530
HK$3,048 total
includes taxes & fees
26 Jul - 27 Jul
Relax at Gulf – Silver Sands Resort #232, Longboat
Marina

Very tropical, private and peaceful, short walk to everything happening downtown

Very tropical, private and peaceful, short walk to everything happening downtown
Central Sarasota
9.6 out of 10, Exceptional, (74 reviews)
"Great neighborhood, easy and safe to walk with the dog.. Size was perfect for what we needed, shaded backyard great to relax. "
United States
Holly A.
The price is HK$777
HK$2,711 total
includes taxes & fees
10 Jul - 11 Jul
Very tropical, private and peaceful, short walk to everything happening downtown
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

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