Legacy Trail Vacation Rentals

Check prices for these dates

In two weeks
Feb 13 - Feb 15
In two months
Mar 27 - Mar 29
In three months
Apr 24 - Apr 26
In four months
May 22 - May 24

Our top choices for Legacy Trail vacation rentals

Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,272 reviews)
"Wonderful stay!"
United States
Victoria
$206 nightly
The price is $233
Feb 3 - Feb 4
Total with taxes and fees
Tropical Beach Resorts
Beach nearby, white sand, sun loungers, 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, (422 reviews)
"Location was perfect and room did the job nicely for our stay."
United States
Marcellena
$204 nightly
The price is $230
Feb 2 - Feb 3
Total with taxes and fees
Haley's at The Anna Maria Island Inn
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, (349 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
$207 nightly
The price is $233
Feb 2 - Feb 3
Total with taxes and fees
Tiny House Siesta
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
$334 nightly
The price is $378
Feb 2 - Feb 3
Total with taxes and fees
Siesta Heron Suites & Villas
Premium bedding, pillowtop beds, minibar, free cribs/infant beds

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (73 reviews)
"The room was clean, the beds were comfy, and the view was incredible!"
United States
Amy
$250 nightly
The price is $283
Feb 3 - Feb 4
Total with taxes and fees
Seabreeze at Anna Maria Island Inn
Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (253 reviews)
"Great place! "
United States
Michelle
$243 nightly
The price is $275
Mar 2 - Mar 3
Total with taxes and fees
Kon Tiki Inn
Interior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.4 out of 10, Exceptional, (13 reviews)
"Property was perfect for the price."
United States
William M.
$145 nightly
The price is $161
Mar 1 - Mar 2
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,244 reviews)
"Very clean, and staff was extremely nice. "
United States
Maribeth
$212 nightly
The price is $240
Feb 3 - Feb 4
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
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, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
$446 nightly
The price is $505
Feb 10 - Feb 11
Total with taxes and fees
The Inn On Siesta Key
Beach nearby, white sand, beach umbrellas, beach towels

Palm Tree Villas

Palm Tree Villas
3.0 star property
Holmes Beach
9.2 out of 10, Wonderful, (172 reviews)
"We had a great stay! The property was located within a short walk to the beach. We will be back!"
United States
Anonymous traveler
$662 nightly
The price is $729
Feb 8 - Feb 9
Total with taxes and fees
Palm Tree Villas
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,193 reviews)
"Excellent place and location, "
United States
Richard
$259 nightly
The price is $291
Feb 2 - Feb 3
Total with taxes and fees
Captiva Beach Resort
Beach nearby, beach towels

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (60 reviews)
"Very good, great location 👍👍"
United States
James M.
$281 nightly
The price is $313
Feb 2 - Feb 3
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
447 Avenida De Mayo, 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, (58 reviews)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
$402 nightly
The price is $454
Feb 2 - Feb 3
Total with taxes and fees
Siesta Key Island Rentals
Living area

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, (16 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
$209 nightly
The price is $234
Feb 4 - Feb 5
Total with taxes and fees
Nestled in North Port. Updated 2 Bed / 1 Bath.
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, (356 reviews)
"Great place…"
United States
Debra
$272 nightly
The price is $308
Feb 3 - Feb 4
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
Beach nearby, sun loungers, beach towels

Two Miles to Siesta Key

Two Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (44 reviews)
"Terry was a great host. The apartment was very comfortable and had everything we needed for our short stay in Sarasota. Would stay here again."
United States
Robert C.
$139 nightly
The price is $154
Feb 4 - Feb 5
Total with taxes and fees
Two Miles to Siesta Key
Outdoor dining

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Sunny Shores
9.4 out of 10, Exceptional, (35 reviews)
"Excellent for a family trip."
United States
RHEA
$495 nightly
The price is $530
Feb 21 - Feb 22
Total with taxes and fees
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Exterior

The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (169 reviews)
"perfect location and size for what we were looking for"
United States
michael w.
$248 nightly
The price is $255
Feb 8 - Feb 9
Total with taxes and fees
The Hideaways at Point Pleasant (Palm Side)
1 bedroom, desk, iron/ironing board, WiFi

The Sapphire Suite 1Bed/1Bath

The Sapphire Suite 1Bed/1Bath
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (90 reviews)
"We loved our stay here, it was a perfect location with lots to do within even walking distance! "
United States
Austin S.
$152 nightly
The price is $169
Mar 2 - Mar 3
Total with taxes and fees
The Sapphire Suite 1Bed/1Bath
On the beach, sun loungers, beach towels

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (112 reviews)
"Simple old-school beach shack - so hard to find these days, absolutely loved it. Right on the water, best location along Nokomis Beach/Casey Key...short walk to restaurants also....absolutely fantastic."
United States
HAYLEY S.
$363 nightly
The price is $407
Feb 2 - Feb 3
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
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

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"Everyone was wonderful"
Leslie 10-night trip
Posted 1 day ago
Tropical Breeze Resort

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Legacy Trail in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $230 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

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