Legacy Trail Vacation Rentals

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Vacation Rentals in Legacy Trail

Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Tropical Beach Resorts

3.5 star property
South Village
9.4 out of 10, Exceptional, (5088)
"Clean, comfortable, and friendly staff."
United States
John
$164 nightly
The price is $185
Nov 11 - Nov 12
Total with taxes and fees
Tropical Beach Resorts
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
South Village
9.6 out of 10, Exceptional, (294)
"We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need. "
United States
Tammy
$396 nightly
The price is $448
Dec 11 - Dec 12
Total with taxes and fees
The Residences at Siesta Key Beach by Hyatt Vacation Club
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, (340)
"Excelente"
Mexico
Carlis
$181 nightly
The price is $205
Dec 7 - Dec 8
Total with taxes and fees
Tiny House Siesta
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, (2191)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
$129 nightly
The price is $146
Nov 11 - Nov 12
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Exterior
Kon Tiki Inn

Kon Tiki Inn

2.5 star property
Venice Island
10.0 out of 10, Exceptional, (241)
"Great place to stay"
United States
Brad
$131 nightly
The price is $149
Nov 11 - Nov 12
Total with taxes and fees
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, (1155)
"Very good stay, clean, safe, and steps from the beach"
United States
Brandon
$167 nightly
The price is $187
Nov 11 - Nov 12
Total with taxes and fees
Captiva Beach Resort
Exterior
Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

3.0 star property
Bradenton Beach
9.2 out of 10, Wonderful, (316)
"Great location"
United States
Michael
$242 nightly
The price is $274
Nov 12 - Nov 13
Total with taxes and fees
Pelican Post at Anna Maria Island Inn
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, (387)
"Shampoos conditioners and lotions, beach towels, cleanliness freshness, thank you it was a good day"
United States
Karen
$158 nightly
The price is $178
Nov 17 - Nov 18
Total with taxes and fees
Haley's at The Anna Maria Island Inn
Front of property
The Ringling Beach House

The Ringling Beach House

3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (335)
"Clean, friendly and beach!"
United States
Mary
The Ringling Beach House
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

The Inn On Siesta Key

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"This property was great and it is a quick walk to the beach and village. The Cabana suited our family of four. We had enough space to spread out and relax. If we return to Siesta Key, we would stay here again."
United States
Brooke
$238 nightly
The price is $269
Nov 11 - Nov 12
Total with taxes and fees
The Inn On Siesta Key
On the beach, white sand
A Beach Retreat

A Beach Retreat

2.5 star property
Casey Key
9.2 out of 10, Wonderful, (569)
"Perfect location beachfront room"
United States
Suzette
$184 nightly
The price is $208
Nov 13 - Nov 14
Total with taxes and fees
A Beach Retreat
Outdoor pool, pool umbrellas, sun loungers
Bridgewalk Resort

Bridgewalk Resort

3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (759)
"Great stay!"
United States
Sufyan
$284 nightly
The price is $321
Nov 11 - Nov 12
Total with taxes and fees
Bridgewalk Resort
Beach nearby
Island Life! King Bed Studio-Steps to beach

Island Life! King Bed Studio-Steps to beach

Manasota Key
9.6 out of 10, Exceptional, (168)
"My husband and I stayed at the Bay Breeze Bungalow for 4 days and cannot wait to come back. Perfect location, 2 minute walk to the beach. Quiet neighborhood. We were right next to the pool, and even with kids swimming, it was quiet. We had a question regarding parking, (our confusion) we received a call back within a 1/2 hour. The Bungalow was very clean and had the essentials we needed. Being May, it was extremely warm, the air conditioner always kept the place cool. I cannot say enough...
United States
Karen L.
$195 nightly
The price is $216
Nov 30 - Dec 1
Total with taxes and fees
Island Life! King Bed Studio-Steps to beach
Exterior detail
Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath

Bayou Oaks
9.4 out of 10, Exceptional, (37)
"Perfect little place for a couple days. Clean and conveniently located just a short drive away from everything you need. Host was responsive and accommodating. We would definitely stay here again. "
United States
Adrianne J.
$105 nightly
The price is $116
Nov 18 - Nov 19
Total with taxes and fees
Riverside Oasis 1Bed/1Bath
Terrace/patio
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite

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

Bradenton
9.4 out of 10, Exceptional, (67)
"Our stay here was just perfect - great location, everything we needed, Bryce left very good instructions for anything that we might have needed (we didn’t 😊), and very comfortable! We were close to everything but felt like we had our own little private place too. Will definitely come back here. "
United States
Maureen
$135 nightly
The price is $150
Nov 11 - Nov 12
Total with taxes and fees
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quite
Property grounds
Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village

Olde Englewood Village
9.8 out of 10, Exceptional, (60)
"Had a nice stay. Clean and well equipped."
United States
Debi D.
$225 nightly
The price is $251
Nov 11 - Nov 12
Total with taxes and fees
Old Floridian cottage in Historic Gulf Village
A heated pool
Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA

Longboat Key
9.2 out of 10, Wonderful, (119)
"Couldn't have been a better spot for our family"
United States
Sandee R.
$286 nightly
The price is $318
Dec 3 - Dec 4
Total with taxes and fees
Oceanfront Oasis – Longboat Key 226 by RVA
On the beach, sun loungers, beach towels
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

Casey Key
9.2 out of 10, Wonderful, (68)
"We so enjoy this little property loved the beach and it’s coziness would definitely refer ones to it and would stay again found lots of shells and sharks teeth"
United States
Bobbie H.
$518 nightly
The price is $577
Nov 15 - Nov 16
Total with taxes and fees
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Beach
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Bradenton
10.0 out of 10, Exceptional, (117)
"The condo was beautiful and very spacious. Nice area and very close to the places we wanted to go."
United States
Brenda S.
$264 nightly
The price is $295
Nov 11 - Nov 12
Total with taxes and fees
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants
Beach nearby, sun loungers, beach towels
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio

Siesta Key Village
9.8 out of 10, Exceptional, (6)
"We enjoyed the location and beach and had a wonderful relaxing stay. It was nice to be able to bring chairs to the beach and walk a short distance. "
United States
Lillian C.
$521 nightly
The price is $581
Nov 22 - Nov 23
Total with taxes and fees
Beach Rd, 300ft to Beach Access & 500ft to Siesta Key Village, Studio
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

Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

10/10 Excellent
"Great place …. Great people … very clean !!! And the breakfast was great !!! "
Camila 1-night trip
Posted 1 day ago
Compass Hotel by Margaritaville Anna Maria Sound

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 $146 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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