Holiday Rentals in Legacy Trail

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Legacy Trail holiday rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (277 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is €122
includes taxes & fees
21 May - 22 May
Kon Tiki Inn

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is €463
includes taxes & fees
28 May - 29 May
Chadwick Cove Resort & Marina

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (67 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is €225
includes taxes & fees
21 May - 22 May
Path to Paradise.

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (480 reviews)
"Clean room, staff was excellent. Close to downtown area and beach, all within walking distance. "
Canada
John
The price is €114
includes taxes & fees
29 May - 30 May
Venice Beach Villas

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (66 reviews)
"Short stay to see a friend that was in the area it was a great olace"
United States
deborah f.
The price is €187
includes taxes & fees
25 May - 26 May
The "Grouper"

Nestled in North Port. Updated 2 Bed / 1 Bath.

Nestled in North Port. Updated 2 Bed / 1 Bath.
North Port
10.0 out of 10, Exceptional, (24 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is €194
includes taxes & fees
24 May - 25 May
Nestled in North Port. Updated 2 Bed / 1 Bath.

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, (450 reviews)
"Great location, clean and quiet. "
United States
Sara
The price is €236
includes taxes & fees
26 May - 27 May
Haley's at The Anna Maria Island Inn

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (127 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
The price is €291
includes taxes & fees
27 May - 28 May
SeaSpray Resort

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (24 reviews)
"Great little place! Wish we could have spent more time"
United States
Tricia W.
The price is €128
includes taxes & fees
21 May - 22 May
Charming cottage for 2 across warm mineral springs park

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,499 reviews)
"This was such a great place to stay. The pool was GREAT and the beach access was fantastic"
United States
Laurie A
The price is €204
includes taxes & fees
31 May - 1 Jun
Tropical Beach Resorts

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,256 reviews)
"Nice place for a relaxing time"
United States
Andres Eduardo
The price is €245
includes taxes & fees
25 May - 26 May
Captiva Beach Resort

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!
Englewood
10.0 out of 10, Exceptional, (57 reviews)
"Great stay at Pura Vida! The host is amazing very attentive to your needs. The place was perfect! Beautifully decorated and super clean! "
United States
Lisa D.
The price is €259
includes taxes & fees
21 May - 22 May
Tiki Life. Tropical Gateway to Boca Grande Beaches! Relax without the costs!!!

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, (65 reviews)
"A fabulous place that was super easy to check in and all communication with the host was prompt. Very relaxing atmosphere"
United States
Tara
The price is €259
includes taxes & fees
2 Jun - 3 Jun
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Bradenton Beach
10.0 out of 10, Exceptional, (21 reviews)
"Great location perfect room for 2 people. "
United States
Macey
The price is €265
includes taxes & fees
21 May - 22 May
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.2 out of 10, Wonderful, (77 reviews)
"Great place to stay!"
United States
Wendi B.
The price is €163
includes taxes & fees
26 May - 27 May
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (634 reviews)
"Love this place"
United States
Marialis
The price is €193
includes taxes & fees
27 May - 28 May
A Beach Retreat

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!
Ridge Wood Heights
10.0 out of 10, Exceptional, (17 reviews)
"Great place. Clean with everything you need"
United States
Thomas Lee
The price is €292
includes taxes & fees
25 May - 26 May
BAREFOOT BUNGALOW- 1O MINUTES TO SIESTA BEACH AND AMENITIES! PET FRIENDLY!

Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (75 reviews)
"Great location in Siesta Key Village, can walk to all the shops and restaurants as well as the beach "
United States
Erica S.
The price is €352
includes taxes & fees
25 May - 26 May
Siesta Key Village-Suite #3: A Block to the Beach!

"Stingray" 3 miles to Anna Marie

"Stingray" 3 miles to Anna Marie
Bradenton
9.6 out of 10, Exceptional, (32 reviews)
"Property was great and location was ideal for our weekend getaway"
United States
Agnieszka
The price is €313
includes taxes & fees
21 May - 22 May
"Stingray" 3 miles to Anna Marie
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Legacy Trail Hotel Reviews

Find out more about Legacy Trail

Everything you need to know about Legacy Trail holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Legacy Trail holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail holiday rentals we have selected for you start as low as €122 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 holiday 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 holiday.

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.