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, (288 reviews)
"Great place to stay!!!"
United States
Tara
The price is NZ$222
includes taxes & fees
29 June - 30 June
Kon Tiki Inn

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
The price is NZ$1,011
includes taxes & fees
19 July - 20 July
Chadwick Cove Resort & Marina

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (69 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is NZ$627
includes taxes & fees
30 June - 1 July
Siesta Key Island Rentals

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, (458 reviews)
"The property served it's purpose of comfort for relaxation. We enjoyed it thoroughly and will make this an annual trip."
United States
Sydney
The price is NZ$411
includes taxes & fees
1 July - 2 July
Haley's at The Anna Maria Island Inn

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,269 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is NZ$360
includes taxes & fees
7 July - 8 July
Captiva Beach Resort

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,599 reviews)
"perfect stay and location for a family!"
United States
Jessica
The price is NZ$351
includes taxes & fees
28 June - 29 June
Tropical Beach Resorts

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (370 reviews)
"Loved the tiny house will stay there again!"
United States
Nydia
The price is NZ$354
includes taxes & fees
1 July - 2 July
Tiny House Siesta

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (643 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
The price is NZ$407
includes taxes & fees
28 June - 29 June
A Beach Retreat

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (71 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is NZ$374
includes taxes & fees
29 June - 30 June
The "Grouper"

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is NZ$877
includes taxes & fees
12 July - 13 July
The Inn On Siesta Key

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts
Englewood
10.0 out of 10, Exceptional, (68 reviews)
"Excellent stay at Pura Vida——-clean, cool rooms, very relaxing experience on the property. It’s obvious Pura Vida put thought into the arrangement of outside amenities, including couches, dining tables, the spa, and numerous fruit trees planted around the property. Would 100% stay here again."
United States
Alex
The price is NZ$527
includes taxes & fees
28 June - 29 June
Tropical Gateway to the Beaches. Caribbean Tiki Hut feeling - w/m discounts

Mimosa Memories

Mimosa Memories
South Venice
9.6 out of 10, Exceptional, (38 reviews)
"We had a very comfortable stay and had all the amenities that we needed."
United States
Susan H.
The price is NZ$582
includes taxes & fees
1 July - 2 July
Mimosa Memories

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (142 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is NZ$536
includes taxes & fees
20 July - 21 July
SeaSpray Resort

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
8.8 out of 10, Excellent, (5 reviews)
"I would stay again, very accommodating"
United States
Deliondra
The price is NZ$1,136
includes taxes & fees
30 June - 1 July
Cedar Run Resort - Roam Hospitality

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, (415 reviews)
"Great location - quiet, private, but just a few blocks from the beach, every eatery and nightlife option. Would definitely stay here again."
United States
Christopher
The price is NZ$389
includes taxes & fees
2 July - 3 July
Pelican Post at Anna Maria Island Inn

[lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (35 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is NZ$614
includes taxes & fees
28 June - 29 June
[lounge like locals] walk to siesta beach +bikes

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,348 reviews)
"great place to stay for a couple of nights. "
United States
Diana
The price is NZ$304
includes taxes & fees
12 July - 13 July
Hibiscus Suites - Gateway to Siesta Key

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (102 reviews)
The price is NZ$615
includes taxes & fees
19 July - 20 July
Oceanfront Bliss–Longboat Key Beach 106 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (96 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is NZ$707
includes taxes & fees
19 July - 20 July
1BR Beach Getaway – Silver Sands #254 by RVA

Very tropical, private and peaceful, short walk to everything happening downtown

Very tropical, private and peaceful, short walk to everything happening downtown
Central Sarasota
9.6 out of 10, Exceptional, (74 reviews)
"We loved the location! The neighborhood is charming and walkable to downtown Sarasota. We loved the secluded garden that was so inviting. Unfortunately, weather didn’t permit us to take advantage of it. We hope to return! "
United States
Christine B.
The price is NZ$644
includes taxes & fees
13 July - 14 July
Very tropical, private and peaceful, short walk to everything happening downtown
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$160 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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