A wooden pathway surrounded by dense greenery and trees.

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, (5,743 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is CA $188
CA $249 total
includes taxes & fees
Sep 7 - Sep 8
Tropical Beach Resorts

2. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,295 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is CA $217
CA $269 total
includes taxes & fees
Aug 12 - Aug 13
Captiva Beach Resort

3. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (383 reviews)
"Great place"
United States
Mario
The price is CA $115
CA $319 total
includes taxes & fees
Aug 12 - Aug 13
Tiny House Siesta

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,400 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
The price is CA $153
CA $173 total
includes taxes & fees
Aug 19 - Aug 20
Hibiscus Suites - Gateway to Siesta Key

5. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (165 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is CA $287
CA $325 total
includes taxes & fees
Sep 1 - Sep 2
SeaSpray Resort

6. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (662 reviews)
"Perfect beach property. Very clean and affordable for the location!"
United States
Bob
The price is CA $257
CA $290 total
includes taxes & fees
Aug 27 - Aug 28
A Beach Retreat

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

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (36 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is CA $201
CA $536 total
includes taxes & fees
Aug 19 - Aug 20
[lounge like locals] walk to siesta beach +bikes

8. 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 $149
CA $370 total
includes taxes & fees
Aug 11 - Aug 12
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

9. 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, (26 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
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.

10. 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, (471 reviews)
"Very clean room and just a short walk to the beach!"
United States
Ivet
The price is CA $190
CA $240 total
includes taxes & fees
Aug 26 - Aug 27
Haley's at The Anna Maria Island Inn

11. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (203 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is CA $324
CA $444 total
includes taxes & fees
Aug 13 - Aug 14
The Inn On Siesta Key

12. Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (89 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
The price is CA $241
CA $506 total
includes taxes & fees
Aug 13 - Aug 14
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

13. Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
South Village
9.4 out of 10, Exceptional, (38 reviews)
"It was a great location with easy access to the pool, beach and entertainment! The place was clean and nice, perfect for our family!"
United States
Emily
The price is CA $242
CA $849 total
includes taxes & fees
Aug 19 - Aug 20
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

14. 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 for the area, super close to all restaurants and just a 5 minute walk to the beach. Good space for a beach vacation and all the amenities were great"
United States
amy b.
The price is CA $213
CA $549 total
includes taxes & fees
Aug 11 - Aug 12
Siesta Cooler: Only Minutes Walk to Siesta Beach!

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

Studio Retreat Across the Street from Beautiful Siesta Key Beach
Siesta Key
8.8 out of 10, Excellent, (166 reviews)
"It was a great place. And just about a 5 min walk to the beach. "
United States
DESIREE
The price is CA $254
CA $434 total
includes taxes & fees
Aug 11 - Aug 12
Studio Retreat Across the Street from Beautiful Siesta Key Beach

16. 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, (443 reviews)
"Great place to stay,"
United States
Wilson
The price is CA $216
CA $274 total
includes taxes & fees
Sep 8 - Sep 9
Pelican Post at Anna Maria Island Inn

17. Lakeview Bradenton Rental Near Beaches & IMG

Lakeview Bradenton Rental Near Beaches & IMG
South Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very clean and comfortable. "
United States
Dee F.
The price is CA $124
CA $316 total
includes taxes & fees
Sep 1 - Sep 2
Lakeview Bradenton Rental Near Beaches & IMG

18. 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, (117 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 traveller
Sunset and beach view from your balcony Unit 403

19. 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, (189 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is CA $302
CA $597 total
includes taxes & fees
Sep 2 - Sep 3
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

20. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (73 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is CA $138
CA $298 total
includes taxes & fees
Aug 12 - Aug 13
The "Grouper"
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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