Legacy Trail Holiday Rentals

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Our top choices for Legacy Trail holiday 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 NZ$227
includes taxes & fees
1 June - 2 June
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
The price is NZ$662
includes taxes & fees
12 May - 13 May
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 NZ$951
includes taxes & fees
14 May - 15 May
Chadwick Cove Resort & Marina

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (65 reviews)
"I would recommend this place to anyone! It was extremely clean and neat, and we had a lovely time here! The host was very responsive and kind too. Overall, this place was above my expectations and a great place to stay."
United States
Lana
The price is NZ$355
includes taxes & fees
16 May - 17 May
The "Grouper"

Path to Paradise.

Path to Paradise.
Olde Englewood Village
The price is NZ$588
includes taxes & fees
12 May - 13 May
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 NZ$368
includes taxes & fees
12 May - 13 May
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)
"Very clean, the host was very good at communication. We were there for an event so we wouldn't have to drive back to Tampa. It was a seamless stay. The host had snacks and small fridge and freezer, coffee maker, air fryer and microwave. It was a older and a little dated, but clean and just what we needed. We would stay again."
United States
Paul Vance R.
The price is NZ$309
includes taxes & fees
12 May - 13 May
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 NZ$484
includes taxes & fees
12 May - 13 May
[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 NZ$251
includes taxes & fees
14 May - 15 May
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, (5,474 reviews)
"Great place to stay, beach 2 minute walk."
United States
Joseph
The price is NZ$348
includes taxes & fees
21 May - 22 May
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 NZ$595
includes taxes & fees
12 May - 13 May
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 NZ$719
includes taxes & fees
12 May - 13 May
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 NZ$544
includes taxes & fees
27 May - 28 May
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 NZ$975
includes taxes & fees
12 May - 13 May
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)
" Clean, easy to get to, well stocked with towels, beach towels, etc. Gorgeous outdoor seating and pool. Would stay again. "
United States
Danielle W.
The price is NZ$601
includes taxes & fees
12 May - 13 May
"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 NZ$699
includes taxes & fees
29 May - 30 May
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 NZ$503
includes taxes & fees
1 June - 2 June
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, (84 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 NZ$681
includes taxes & fees
12 May - 13 May
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, (631 reviews)
"Love this place"
United States
Marialis
The price is NZ$376
includes taxes & fees
18 May - 19 May
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 NZ$576
includes taxes & fees
13 May - 14 May
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

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$227 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.