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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, (5,856 reviews)
"This place is awesome, super clean close to the beach and the pool small But completely renovated and great"
United States
Diana
$158 nightly
The price is $179
Sep 10 - Sep 11
Total with taxes and fees
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, (2,441 reviews)
"This place was perfect!"
United States
Kat
$106 nightly
The price is $120
Sep 10 - Sep 11
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

3. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (178 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
$214 nightly
The price is $242
Sep 28 - Sep 29
Total with taxes and fees
SeaSpray Resort

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,305 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
$178 nightly
The price is $199
Sep 10 - Sep 11
Total with taxes and fees
Captiva Beach Resort

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (676 reviews)
"Great stay!!"
United States
Genghis
$205 nightly
The price is $231
Sep 10 - Sep 11
Total with taxes and fees
A Beach Retreat

6. Bridgewalk Resort

Bridgewalk Resort
3.5 star property
Bridge Street
9.4 out of 10, Exceptional, (827 reviews)
"The hotel was wonderful. Nice staff, room and location. Free beach chairs, towels and umbrella to use at the beach which is right across the street."
United States
robin
$294 nightly
The price is $332
Sep 13 - Sep 14
Total with taxes and fees
Bridgewalk Resort

7. 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
$408 nightly
The price is $455
Sep 10 - Sep 11
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA

8. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (191 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
$383 nightly
The price is $427
Sep 13 - Sep 14
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9. 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.
$423 nightly
The price is $472
Sep 10 - Sep 11
Total with taxes and fees
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

10. House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
South Village
9.2 out of 10, Wonderful, (144 reviews)
"Accommodations were perfect for our family of 6. Extremely convenient to have private beach access along with chairs and ability to get umbrellas for shade."
United States
James N.
$739 nightly
The price is $824
Sep 21 - Sep 22
Total with taxes and fees
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

11. Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA

Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA
South Village
9.2 out of 10, Wonderful, (103 reviews)
"very close to the beach"
United States
Carleen D.
$405 nightly
The price is $452
Sep 10 - Sep 11
Total with taxes and fees
Beach Days, Home Nights 2BR w/ Kitchen-Beach Club at Siesta Key #103E by RVA

12. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (131 reviews)
"A beautiful location and super comfortable!"
United States
K B.
$426 nightly
The price is $475
Sep 11 - Sep 12
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

13. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
$302 nightly
The price is $308
Sep 16 - Sep 17
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes

14. 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
$258 nightly
The price is $289
Sep 14 - Sep 15
Total with taxes and fees
Studio Retreat Across the Street from Beautiful Siesta Key Beach

15. 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, (455 reviews)
"Great place to stay,"
United States
Wilson
$185 nightly
The price is $209
Sep 20 - Sep 21
Total with taxes and fees
Pelican Post at Anna Maria Island Inn

16. Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!
Siesta Key Village
10.0 out of 10, Exceptional, (38 reviews)
"Excellent location to everything and the hosts were very accommodating! Will book this place again!"
United States
Christopher B.
$570 nightly
The price is $636
Sep 14 - Sep 15
Total with taxes and fees
Sea Foam - Pet Friendly, Located in Siesta Key Village, Steps to Siesta Key Beach!

17. 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.
$368 nightly
The price is $398
Sep 10 - Sep 11
Total with taxes and fees
Siesta Cooler: Only Minutes Walk to Siesta Beach!

18. 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.
$225 nightly
The price is $251
Sep 10 - Sep 11
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

19. Sunset and beach view from your balcony Unit 403

Sunset and beach view from your balcony Unit 403
Longboat Key
9.8 out of 10, Exceptional, (119 reviews)
"TCI is a great place to stay. Close to the beach, grocery store, shopping and walking paths. The condo was very clean and has all the amenities needed. The staff if very approachable and easy to connect with for any questions. This is our 2nd stay and we will return."
United States
Anonymous traveler
$360 nightly
The price is $397
Oct 10 - Oct 11
Total with taxes and fees
Sunset and beach view from your balcony Unit 403

20. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.2 out of 10, Wonderful, (26 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
$563 nightly
The price is $606
Sep 12 - Sep 13
Total with taxes and fees
Chadwick Cove Resort & Marina
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

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 $90 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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