A wooden pathway surrounded by dense greenery and trees.

Legacy Trail Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Legacy Trail holiday rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

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 NZ$312
includes taxes & fees
29 Sept - 30 Sept
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

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 NZ$237
includes taxes & fees
27 Sept - 28 Sept
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

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 NZ$321
includes taxes & fees
29 Sept - 30 Sept
Captiva Beach Resort
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

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 NZ$416
includes taxes & fees
4 Oct - 5 Oct
SeaSpray Resort
A hotel with a balcony and palm trees.

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
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

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 NZ$364
includes taxes & fees
27 Sept - 28 Sept
A Beach Retreat
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

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 NZ$457
includes taxes & fees
27 Sept - 28 Sept
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A modern bedroom with a bed, a bedside table, a round dining table with chairs, and a large window with curtains.

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 NZ$504
includes taxes & fees
27 Sept - 28 Sept
[escape to paradise] siesta key beach getaway
A beach with tall grasses and a sunset.

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 NZ$469
includes taxes & fees
25 Sept - 26 Sept
Beachside Studio Located Across from Main Beach and Half Mile to Village
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 NZ$608
includes taxes & fees
25 Sept - 26 Sept
Romantic Getaway Beach Club Siesta 202B by RVA
A beach with a wooden picnic table, palm trees, and a clear blue sea.

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 NZ$508
includes taxes & fees
28 Sept - 29 Sept
Studio Retreat Across the Street from Beautiful Siesta Key Beach
A beach with clear turquoise water and a sandy shore.

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 NZ$678
includes taxes & fees
27 Sept - 28 Sept
Siesta Cooler: Only Minutes Walk to Siesta Beach!
A beach with tall grasses and a sunset.

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.
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway
A room with a sliding glass door leading to an outdoor area with a pool and chairs. There is a brown leather sofa with patterned cushions and a framed picture on the wall.

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
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
A modern kitchen with a central island, bar stools, a window, and a dark cabinet.

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 NZ$403
includes taxes & fees
27 Sept - 28 Sept
Secluded Cottage with Hot Tub, Walking Distance to Benderson and UTC.
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 NZ$820
includes taxes & fees
25 Sept - 26 Sept
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A wooden pathway leading to a beach with lush greenery on either side.

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 NZ$549
includes taxes & fees
7 Oct - 8 Oct
Oceanfront Oasis – Longboat Key 226 by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 NZ$822
includes taxes & fees
25 Sept - 26 Sept
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
A beach with clear turquoise water and a sandy shore.

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 NZ$370
includes taxes & fees
29 Sept - 30 Sept
The "Grouper"
A modern living room with a large window, a flat-screen TV, and a potted plant.

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 NZ$374
includes taxes & fees
27 Sept - 28 Sept
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

Everything you need to know about Legacy Trail holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Legacy Trail holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Legacy Trail holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Legacy Trail holiday rentals we have selected for you start as low as NZ$140 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail holiday 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 holiday.

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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