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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 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, (288 reviews)
"Great place to stay!!!"
United States
Tara
The price is 3.298.023 ₫
3.726.767 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Kon Tiki Inn
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is 2.917.130 ₫
15.115.235 ₫ total
includes taxes & fees
14 Jul - 15 Jul
Chadwick Cove Resort & Marina
5365 Calle Florida, Siesta Key, FL W/Pool | 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 3.662.364 ₫
9.700.713 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Siesta Key Island Rentals
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, (458 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 4.826.000 ₫
6.107.785 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Haley's at The Anna Maria Island Inn
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,269 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is 4.341.126 ₫
5.351.749 ₫ total
includes taxes & fees
7 Jul - 8 Jul
Captiva Beach Resort
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,599 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is 4.005.957 ₫
5.211.022 ₫ total
includes taxes & fees
28 Jun - 29 Jun
Tropical Beach Resorts
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

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 1.825.916 ₫
5.262.114 ₫ total
includes taxes & fees
1 Jul - 2 Jul
Tiny House Siesta
Beachside One Bedroom Suite | 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, (643 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is 5.349.263 ₫
6.044.612 ₫ total
includes taxes & fees
29 Jun - 30 Jun
A Beach Retreat
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 10.707.741 ₫
13.736.095 ₫ total
includes taxes & fees
6 Jul - 7 Jul
The Inn On Siesta Key
Superior Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (142 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is 7.083.519 ₫
8.004.561 ₫ total
includes taxes & fees
20 Jul - 21 Jul
SeaSpray Resort
Outdoor pool, pool umbrellas, pool loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
8.8 out of 10, Excellent, (5 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is 3.975.679 ₫
16.864.250 ₫ total
includes taxes & fees
30 Jun - 1 Jul
Cedar Run Resort - Roam Hospitality
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, (415 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 5.363.996 ₫
6.788.673 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Pelican Post at Anna Maria Island Inn
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, (2,348 reviews)
"great place to stay for a couple of nights. "
United States
Diana
The price is 3.922.533 ₫
4.432.463 ₫ total
includes taxes & fees
29 Jun - 30 Jun
Hibiscus Suites - Gateway to Siesta Key
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