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Legacy Trail Vacation Rentals

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Our top choices for Legacy Trail vacation rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,916 reviews)
"Amazing resort,"
United States
kurt
The price is CA $190
CA $251 total
includes taxes & fees
Sep 29 - Sep 30
Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,452 reviews)
"This place was perfect!"
United States
Kat
The price is CA $155
CA $176 total
includes taxes & fees
Sep 29 - Sep 30
Hibiscus Suites - Gateway to Siesta Key

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,309 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $208
CA $259 total
includes taxes & fees
Sep 29 - Sep 30
Captiva Beach Resort

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (181 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is CA $291
CA $329 total
includes taxes & fees
Oct 25 - Oct 26
SeaSpray Resort

5. The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
8.8 out of 10, Excellent, (391 reviews)
"Very clean and nice areas."
United States
DANTE
The Ringling Beach House

6. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (682 reviews)
"Great stay!!"
United States
Genghis
The price is CA $260
CA $294 total
includes taxes & fees
Sep 27 - Sep 28
A Beach Retreat

7. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is CA $150
CA $377 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

8. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 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 $123
CA $423 total
includes taxes & fees
Sep 28 - Sep 29
[escape to paradise] siesta key beach getaway

9. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (170 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
The price is CA $209
CA $376 total
includes taxes & fees
Sep 25 - Sep 26
Beachside Studio Located Across from Main Beach and Half Mile to Village

10. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA
South Village
8.8 out of 10, Excellent, (57 reviews)
"Peaceful getaway. Throughly enjoyed the stay. "
United States
Anonymous traveller
The price is CA $239
CA $506 total
includes taxes & fees
Sep 29 - Sep 30
Romantic Getaway Beach Club Siesta 202B by RVA

11. Studio Retreat Across the Street from Beautiful Siesta Key Beach

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
9.0 out of 10, Wonderful, (167 reviews)
"It was a great place. And just about a 5 min walk to the beach. "
United States
DESIREE
The price is CA $231
CA $411 total
includes taxes & fees
Sep 28 - Sep 29
Studio Retreat Across the Street from Beautiful Siesta Key Beach

12. Siesta Cooler: Only Minutes Walk to Siesta Beach!

Siesta Cooler: Only Minutes Walk to Siesta Beach!
Siesta Key Village
9.6 out of 10, Exceptional, (75 reviews)
"great location- clean "
United States
Jon W.
The price is CA $225
CA $567 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Cooler: Only Minutes Walk to Siesta Beach!

13. Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
Siesta Key
9.4 out of 10, Exceptional, (144 reviews)
"We loved it!"
United States
John S.
The price is CA $249
CA $434 total
includes taxes & fees
Sep 28 - Sep 29
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

14. Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (100 reviews)
"Great location"
United States
Daphane
The price is CA $300
CA $526 total
includes taxes & fees
Sep 28 - Sep 29
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

15. Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
The Meadows
10.0 out of 10, Exceptional, (27 reviews)
"The perfect place and the best rental I’ve stayed in!! All the descriptions are perfect. If you’re looking for a private getaway that’s close and cozy, this is it."
United States
Emma
The price is CA $121
CA $309 total
includes taxes & fees
Oct 20 - Oct 21
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

16. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Good"
United States
Gelsy
The price is CA $280
CA $667 total
includes taxes & fees
Sep 28 - Sep 29
2BR Beach Style w Pool Beach Club Siesta 204C RVA

17. Oceanfront Oasis – Longboat Key 226 by RVA

Oceanfront Oasis – Longboat Key 226 by RVA
Longboat Key
9.2 out of 10, Wonderful, (140 reviews)
"We loved it and recommend it and definitely plan another. Locals only lol."
United States
Kenneth
The price is CA $200
CA $452 total
includes taxes & fees
Oct 7 - Oct 8
Oceanfront Oasis – Longboat Key 226 by RVA

18. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"We found this property to be delightful. We loved the balcony for enjoying our evenings. I would have liked to see a table on the balcony for eating at, it is FL, and I wanted to sit outside for my meals. It was a very close walk to the beach, the pool and hot tub were in excellent working condition. We enjoyed the property. We had a problem, but they had maintenance there within an hour to fix it, I call that a win for the property. "
United States
Jackie J.
The price is CA $281
CA $632 total
includes taxes & fees
Sep 26 - Sep 27
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

19. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is CA $139
CA $298 total
includes taxes & fees
Sep 29 - Sep 30
The "Grouper"

20. 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, (25 reviews)
"Every part of this stay was perfect! "
United States
Stephen P.
The price is CA $115
CA $302 total
includes taxes & fees
Sep 27 - Sep 28
Nestled in North Port. Updated 2 Bed / 1 Bath.
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.

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