Legacy Trail Vacation Rentals

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Vacation Rentals in Legacy Trail

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4948)
"Wonderful resort "
The price is CA $193
CA $249 total
includes taxes & fees
Sep 7 - Sep 8
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2169)
"Friendly staff, room was really clean!"
The price is CA $165
CA $186 total
includes taxes & fees
Sep 7 - Sep 8
Hibiscus Suites - Gateway to Siesta Key

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1128)
"2nd time and excellent as always..close to the beach and great surroundings "
The price is CA $214
CA $265 total
includes taxes & fees
Sep 7 - Sep 8
Captiva Beach Resort

SeaSpray Resort

4.0 star property
9.6 out of 10, Exceptional, (32)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
The price is CA $316
CA $358 total
includes taxes & fees
Sep 9 - Sep 10
SeaSpray Resort

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (321)
"Its a nice little family spot"
The Ringling Beach House

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

9.8 out of 10, Exceptional, (24)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Pelican Post at Anna Maria Island Inn

3.0 star property
9.2 out of 10, Wonderful, (298)
"Place was very clean and perfect location for the beach/surrounding restaurants."
The price is CA $226
CA $287 total
includes taxes & fees
Sep 9 - Sep 10
Pelican Post at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

3.0 star property
9.0 out of 10, Wonderful, (34)
"Awesome place to stay "
The price is CA $304
CA $385 total
includes taxes & fees
Oct 7 - Oct 8
Seabreeze at Anna Maria Island Inn

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (320)
"Super helpful staff."
The price is CA $110
CA $202 total
includes taxes & fees
Sep 8 - Sep 9
Tiny House Siesta

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (229)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
Kon Tiki Inn

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (127)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

Bridgewalk Resort

3.5 star property
9.2 out of 10, Wonderful, (738)
"Very nice rooms and location "
The price is CA $351
CA $397 total
includes taxes & fees
Sep 9 - Sep 10
Bridgewalk Resort

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (43)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (286)
"Great location. Everyone was very friendly and accommodating!"
The price is CA $547
CA $688 total
includes taxes & fees
Sep 29 - Sep 30
The Residences at Siesta Key Beach by Hyatt Vacation Club

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (4)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
Private Home Directly on Siesta Key Beach!

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (47)
"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 CA $145
CA $367 total
includes taxes & fees
Sep 7 - Sep 8
Siesta Key Island Rentals

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (434)
"Clean and welcoming property"
Venice Beach Villas

Tradewinds Beach Resort

2.5 star property
9.2 out of 10, Wonderful, (383)
"Very cute place and easy to walk to beach "
Tradewinds Beach Resort

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The Inn On 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

Find out more about Legacy Trail

Find out more about Legacy Trail

Everything you need to know about Legacy Trail vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Legacy Trail vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Legacy Trail vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Legacy Trail. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Legacy Trail vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail vacation rentals we have selected for you start as low as CA $110 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Legacy Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Legacy Trail vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Legacy Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.