Legacy Trail Vacation Rentals

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Our top choices for Legacy Trail vacation rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (276 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is CA $160
CA $181 total
includes taxes & fees
Jun 4 - Jun 5
Kon Tiki Inn

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals

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 CA $145
CA $778 total
includes taxes & fees
May 14 - May 15
Chadwick Cove Resort & Marina

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (65 reviews)
"Short stay to see a friend that was in the area it was a great olace"
United States
deborah f.
The price is CA $135
CA $293 total
includes taxes & fees
May 16 - May 17
The "Grouper"

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is CA $130
CA $400 total
includes taxes & fees
May 15 - May 16
Path to Paradise.

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,250 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is CA $245
CA $300 total
includes taxes & fees
May 14 - May 15
Captiva Beach Resort

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 CA $151
CA $253 total
includes taxes & fees
May 15 - May 16
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (30 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is CA $194
CA $499 total
includes taxes & fees
May 17 - May 18
[escape to paradise] siesta key beach getaway

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)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is CA $68
CA $198 total
includes taxes & fees
May 14 - May 15
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, (5,479 reviews)
"Loved our stay, room was beautiful and bed was so comfy! So close to the beach, perfect location. Would definitely stay again!"
United States
Amberly
The price is CA $220
CA $284 total
includes taxes & fees
May 20 - May 21
Tropical Beach Resorts

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, (16 reviews)
"Beautiful property, well stocked with all the essentials plus some and extremely clean. The host was kind and helpful. We really enjoyed our stay! "
United States
Hannah H.
The price is CA $197
CA $492 total
includes taxes & fees
May 14 - May 15
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, (73 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 CA $254
CA $598 total
includes taxes & fees
May 25 - May 26
Siesta Key Village-Suite #3: A Block to the Beach!

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (123 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
The price is CA $393
CA $444 total
includes taxes & fees
Jun 10 - Jun 11
SeaSpray Resort

Beach Condo with Pool Near Holmes Beach!

Beach Condo with Pool Near Holmes Beach!
Holmes Beach
9.0 out of 10, Wonderful, (40 reviews)
"Everything was as expected and the location is great."
United States
Thomas T.
The price is CA $402
CA $1,003 total
includes taxes & fees
May 25 - May 26
Beach Condo with Pool Near Holmes 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 CA $260
CA $504 total
includes taxes & fees
Jun 1 - Jun 2
"Stingray" 3 miles to Anna Marie

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Everything was great "
United States
kirt v.
The price is CA $251
CA $574 total
includes taxes & fees
May 29 - May 30
Best views of the beach from your balcony Unit 301

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (120 reviews)
"Perfect spot and host "
United States
Dee B.
The price is CA $162
CA $425 total
includes taxes & fees
Jun 1 - Jun 2
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (85 reviews)
"Beautiful condo!! The owner was very responsive and attentive. We will definitely recommend this place to anyone!"
United States
Kay C.
The price is CA $243
CA $564 total
includes taxes & fees
May 15 - May 16
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (633 reviews)
"Love this place"
United States
Marialis
The price is CA $278
CA $314 total
includes taxes & fees
May 14 - May 15
A Beach Retreat

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (80 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
The price is CA $342
CA $679 total
includes taxes & fees
Jun 3 - Jun 4
Drift & Dune – Longboat Beachfront #101 RVA
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Legacy Trail. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.