Holiday Rentals in Legacy Trail

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Our top choices for Legacy Trail holiday rentals

Christian Retreat Conference Center

Christian Retreat Conference Center
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (2 reviews)
"The room was clean and comfortable. The staff was courteous. The amenities were fabulous! God bless!"
United States
Javier
The price is €113
includes taxes & fees
1 Mar - 2 Mar
Christian Retreat Conference Center

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (351 reviews)
"Clean room, easy check in, beach nearby 15 minute walk, Florida Fun Rides scooter rental place nearby"
United States
Justice
The price is €180
includes taxes & fees
5 Mar - 6 Mar
Tiny House Siesta

#3 Small house walking distance to Warm Mineral Spring

#3 Small house walking distance to Warm Mineral Spring
Warm Mineral Springs
9.0 out of 10, Wonderful, (12 reviews)
"Property was very nice and exactly what I was looking for while working remote. Would absolutely recommend it to anyone and look forward to coming back in the future."
United States
Jake R.
The price is €145
includes taxes & fees
1 Mar - 2 Mar
#3 Small house walking distance to Warm Mineral Spring

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (46 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
The price is €182
includes taxes & fees
4 Mar - 5 Mar
The "Grouper"

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (14 reviews)
"Property was perfect for the price."
United States
William M.
The price is €140
includes taxes & fees
2 Mar - 3 Mar
Charming cottage for 2 across warm mineral springs park

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 €269
includes taxes & fees
20 Feb - 21 Feb
Old Floridian cottage in Historic Gulf Village

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 €531
includes taxes & fees
27 Feb - 28 Feb
Chadwick Cove Resort & Marina

Myakka River

Myakka River
Venice
9.8 out of 10, Exceptional, (19 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 €388
includes taxes & fees
27 Feb - 28 Feb
Myakka River

Riverside Oasis 1Bed/1Bath

Riverside Oasis 1Bed/1Bath
Bayou Oaks
9.2 out of 10, Wonderful, (44 reviews)
"Excellent place to stay"
United States
garry s.
The price is €113
includes taxes & fees
4 Mar - 5 Mar
Riverside Oasis 1Bed/1Bath

Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (45 reviews)
"The apartment is clean and comfortable! Location is amazing! The beach, restaurants, and bars are all very close. The beach is great and easily accessible. 100% would stay here again! "
United States
Alex
Siesta Key Village-Suite #1: A block to the Beach!

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, (17 reviews)
"Great place loved how clean and put together everything was would definitely stay here again"
United States
Jacob
The price is €228
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 €221
includes taxes & fees
24 Feb - 25 Feb
The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Pine Side)

The Hideaways at Point Pleasant (Pine Side)
Bradenton
9.8 out of 10, Exceptional, (175 reviews)
"The property is nice and comfortably equipped. The location is very good."
United States
carlos b.
The price is €218
includes taxes & fees
11 Mar - 12 Mar
The Hideaways at Point Pleasant (Pine Side)

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (74 reviews)
"Very nice place, clean and quiet. Staff very accommodating and professional. Definitely 5 star. "
United States
K M.
The price is €266
includes taxes & fees
25 Feb - 26 Feb
Beachfront Studio – Cabana #5B by RVA

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl
Bradenton
9.8 out of 10, Exceptional, (135 reviews)
"Only went to pool 1 day as spent most of the time at the beach its a nice area with lots to do and lots of nice walks and great beaches "
United Kingdom
David C.
The price is €323
includes taxes & fees
24 Feb - 25 Feb
*Villa Bella* Executive 2BR Condo w/2 Pools, Mins to IMG/Beach/Anna Maria Isl

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
Sunny Shores
9.4 out of 10, Exceptional, (35 reviews)
"Excellent for a family trip."
United States
RHEA
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!

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, (63 reviews)
"Host was great, clean room, balcony was nice. It’s on the Main Street so not quite until the bars closed. Overall a great place to visit. "
United States
Brandon N.
Siesta Cooler: Only Minutes Walk to Siesta Beach!

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 €266
includes taxes & fees
2 Mar - 3 Mar
Kon Tiki Inn

[escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (26 reviews)
"Clean and comfortable. "
United States
Laney
The price is €380
includes taxes & fees
8 Mar - 9 Mar
[escape to paradise] siesta key beach getaway

Freshly Remodeled Island Suite w/ Pool & Pet Friendly

Freshly Remodeled Island Suite w/ Pool & Pet Friendly
Anna Maria
8.2 out of 10, Very good, (44 reviews)
"Nice warm pool, great they had some beach stuff to use, very quiet and nice stay."
United States
Isaac L.
Freshly Remodeled Island Suite w/ Pool & Pet Friendly
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, apart-hotels, 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 €180 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.