Legacy Trail Holiday Rentals

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Our top choices for Legacy Trail holiday 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, (425 reviews)
"Location was perfect and room did the job nicely for our stay."
United States
Marcellena
The price is NZ$738
includes taxes & fees
16 Feb - 17 Feb
Haley's at The Anna Maria Island Inn

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (350 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is NZ$363
includes taxes & fees
5 Mar - 6 Mar
Tiny House Siesta

Christian Retreat Conference Center

Christian Retreat Conference Center
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (1 review)
"Wonderful environment, caring staff who went above and beyond to make sure I was comfortable"
United States
Benjamin
The price is NZ$219
includes taxes & fees
11 Feb - 12 Feb
Christian Retreat Conference Center

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.4 out of 10, Exceptional, (13 reviews)
"Property was perfect for the price."
United States
William M.
The price is NZ$266
includes taxes & fees
1 Mar - 2 Mar
Charming cottage for 2 across warm mineral springs park

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn
3.0 star property
Bradenton Beach
9.0 out of 10, Wonderful, (76 reviews)
"The room was clean, the beds were comfy, and the view was incredible!"
United States
Amy
The price is NZ$1,115
includes taxes & fees
16 Feb - 17 Feb
Seabreeze at Anna Maria Island Inn

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (254 reviews)
"Great place! "
United States
Michelle
The price is NZ$544
includes taxes & fees
16 Feb - 17 Feb
Kon Tiki Inn

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,295 reviews)
"Wonderful stay!"
United States
Victoria
The price is NZ$502
includes taxes & fees
11 Feb - 12 Feb
Tropical Beach Resorts

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, (363 reviews)
"Great place…"
United States
Debra
The price is NZ$819
includes taxes & fees
16 Feb - 17 Feb
Pelican Post at Anna Maria Island Inn

Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village
Olde Englewood Village
9.8 out of 10, Exceptional, (60 reviews)
"Very good, great location 👍👍"
United States
James M.
The price is NZ$515
includes taxes & fees
13 Feb - 14 Feb
Old Floridian cottage in Historic Gulf Village

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
The price is NZ$992
includes taxes & fees
16 Feb - 17 Feb
The Inn On Siesta Key

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, (16 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is NZ$512
includes taxes & fees
1 Mar - 2 Mar
Nestled in North Port. Updated 2 Bed / 1 Bath.

The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)
Bradenton
10.0 out of 10, Exceptional, (169 reviews)
"perfect location and size for what we were looking for"
United States
michael w.
The price is NZ$425
includes taxes & fees
24 Feb - 25 Feb
The Hideaways at Point Pleasant (Palm Side)

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (596 reviews)
"The location is ideal, rooms are nice and the owners are extremely accommodating. "
United States
Catherine
A Beach Retreat

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet
Bradenton
9.4 out of 10, Exceptional, (70 reviews)
"Great place to stay!"
United States
Wendi B.
The price is NZ$322
includes taxes & fees
9 Mar - 10 Mar
1Bedroom✔1Bathroom✔ Livingroom✔ Beach Get Away✔ Pool access✔ Quiet

Premier Waterfront Room, Tiki Bar & Grill, Live Music, Pool, Gym, Kitchenette

Premier Waterfront Room, Tiki Bar & Grill, Live Music, Pool, Gym, Kitchenette
Whitfield Estates
9.6 out of 10, Exceptional, (27 reviews)
"Great stay! "
United States
Natalie P.
The price is NZ$471
includes taxes & fees
1 Mar - 2 Mar
Premier Waterfront Room, Tiki Bar & Grill, Live Music, Pool, Gym, Kitchenette

Myakka River

Myakka River
Venice
9.8 out of 10, Exceptional, (18 reviews)
"We loved everything about the property it’s nice and quiet. Nicely decorated and has a nice outdoor area and dock. The bed was a little firm for my taste but not terrible. 10/10 would stay here again "
United States
Ty
The price is NZ$749
includes taxes & fees
13 Feb - 14 Feb
Myakka River

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (16 reviews)
"Great place and location "
United States
Cathy
The price is NZ$1,216
includes taxes & fees
15 Feb - 16 Feb
Chadwick Cove Resort & Marina

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (112 reviews)
"Simple old-school beach shack - so hard to find these days, absolutely loved it. Right on the water, best location along Nokomis Beach/Casey Key...short walk to restaurants also....absolutely fantastic."
United States
HAYLEY S.
The price is NZ$741
includes taxes & fees
17 Feb - 18 Feb
Casey Key Beachfront Escape: Charming 1BR Cottage

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, (67 reviews)
"Second time staying here. Great location. "
United States
Nathan H.
The price is NZ$629
includes taxes & fees
11 Feb - 12 Feb
Siesta Key Village-Suite #3: A Block to the Beach!

Ground Floor, Steps to Sand – Silver Sands #243A by RVA

Ground Floor, Steps to Sand – Silver Sands #243A by RVA
Longboat Key
8.6 out of 10, Excellent, (62 reviews)
"Super beautiful beach and heated pool. So nice. My room had zero view but it was fine. You are there for beach. Not the room. It was clean. Pool was so clear and warm! Coffee pot, refrig and micro all good. Bed was comfy. No sink in apt except bathroom sink. Awkward. But fine. Sunrise to sunset . "
United States
Pamela
The price is NZ$636
includes taxes & fees
21 Feb - 22 Feb
Ground Floor, Steps to Sand – Silver Sands #243A by 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$375 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.