Holiday Homes in Legacy Trail

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov

Featured Holiday Homes in Legacy Trail and around

Chic happens 3/2pool 5min from Siesta
Exterior

Chic happens 3/2pool 5min from Siesta

The price is €517
includes taxes & fees
22 Sept - 23 Sept
Chic happens 3/2pool 5min from Siesta
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas
Charming 2-bedroom house in Englewood with WiFi and AC
Beach

Charming 2-bedroom house in Englewood with WiFi and AC

Charming 2-bedroom house in Englewood with WiFi and AC
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Property grounds

Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

2.0 star property
10.0 out of 10, Exceptional, (18)
"Great stay! Nice place and location!"
The price is €302
includes taxes & fees
21 Sept - 22 Sept
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
(A) Beautiful home 28 minutes from the beach. 2 bedroom home.
Fridge, microwave, oven, stovetop

(A) Beautiful home 28 minutes from the beach. 2 bedroom home.

9.4 out of 10, Exceptional, (30)
"We have enjoyed the stay very much! "
The price is €223
includes taxes & fees
3 Sept - 4 Sept
(A) Beautiful home 28 minutes from the beach. 2 bedroom home.
Heated Pool & Luxurious Spa! Close to Mineral Springs & Beaches!☀️🌴
Outdoor spa tub

Heated Pool & Luxurious Spa! Close to Mineral Springs & Beaches!☀️🌴

9.8 out of 10, Exceptional, (24)
"Me and my family really enjoyed our stay at this home and will definitely recommend it to anybody."
Heated Pool & Luxurious Spa! Close to Mineral Springs & Beaches!☀️🌴
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Beach

Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

9.6 out of 10, Exceptional, (35)
"Looking forward to staying there again."
The price is €388
includes taxes & fees
24 Aug - 25 Aug
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
September discount,15 mins to AMI, walk to Main St
1 bedroom, iron/ironing board, travel cot, free WiFi

September discount,15 mins to AMI, walk to Main St

2.0 star property
10.0 out of 10, Exceptional, (10)
"Nice little spot close to downtown Bradenton. "
The price is €265
includes taxes & fees
27 Aug - 28 Aug
September discount,15 mins to AMI, walk to Main St
Myakka River
Fridge, microwave, oven, stovetop

Myakka River

9.8 out of 10, Exceptional, (18)
"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 "
The price is €388
includes taxes & fees
24 Aug - 25 Aug
Myakka River
Bradenton Breeze
Deluxe Villa | Living area

Bradenton Breeze

4.0 star property
6.0 out of 10, (2)
"It was good! "
The price is €420
includes taxes & fees
26 Aug - 27 Aug
Bradenton Breeze
Charming home near Anna Maria Island with Jacuzzi
Smart TV, stereo

Charming home near Anna Maria Island with Jacuzzi

2.0 star property
10.0 out of 10, Exceptional, (14)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
The price is €238
includes taxes & fees
29 Aug - 30 Aug
Charming home near Anna Maria Island with Jacuzzi
Waterfront Getaway, a Boating Paradise
Property grounds

Waterfront Getaway, a Boating Paradise

10.0 out of 10, Exceptional, (41)
"Great place to stay with your boat."
The price is €267
includes taxes & fees
24 Aug - 25 Aug
Waterfront Getaway, a Boating Paradise
Tiny House Yellow Lifeguard Stand- pet friendly
Interior

Tiny House Yellow Lifeguard Stand- pet friendly

9.6 out of 10, Exceptional, (43)
"We enjoyed the stay and it worked well. "
The price is €171
includes taxes & fees
26 Aug - 27 Aug
Tiny House Yellow Lifeguard Stand- pet friendly
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
Outdoor dining

LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...

9.4 out of 10, Exceptional, (35)
"Excellent for a family trip."
The price is €434
includes taxes & fees
30 Aug - 31 Aug
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just...
A Piece of Heaven, Waterfront Home, Heated Screened Pool & in Port Charlotte
Outdoor dining

A Piece of Heaven, Waterfront Home, Heated Screened Pool & in Port Charlotte

9.2 out of 10, Wonderful, (64)
"We really enjoyed our stay great house"
A Piece of Heaven, Waterfront Home, Heated Screened Pool & in Port Charlotte
Stylish house minutes from the beach
Fridge, microwave, oven, stovetop

Stylish house minutes from the beach

9.6 out of 10, Exceptional, (25)
"Great location and safe neighborhood. Definitely will stay again if available."
Stylish house minutes from the beach
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home
House, 3 Bedrooms | Property grounds

Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home

3.0 star property
The price is €371
includes taxes & fees
3 Sept - 4 Sept
Elwood Park Gem: Spacious 3br Prime Location 3 Bedroom Home
2 Bedroom 2 Bath home near Siesta Key Beach
Exterior

2 Bedroom 2 Bath home near Siesta Key Beach

8.4 out of 10, Very good, (28)
"The house was great forour family vacation. The location was close to everything we wanted to do. Would definitely stay here again!"
2 Bedroom 2 Bath home near Siesta Key Beach
Paradise Cove -- A perfect Beach Getaway
Beach

Paradise Cove -- A perfect Beach Getaway

10.0 out of 10, Exceptional, (127)
"This property was excellent. It suited all of our needs. Plenty of space and sleeping arrangements. Excellent communication. Excellent location. Kids had a blast in the pool, overall experience was amazing. "
Paradise Cove -- A perfect Beach Getaway
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
Pool

Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches

10.0 out of 10, Exceptional, (28)
"The home was very clean and comfortable Great communication with the host. "
The price is €281
includes taxes & fees
1 Sept - 2 Sept
Water Front Sunny Relaxing Vacation Home 3bds, 2 bath, close to gulf beaches
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Legacy Trail Hotel Reviews

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"We stayed here for 6 nights from August 16-22. It was everything and more! Single mom traveling with 16 year old twin boys was a new experience. We were upgraded upon check-in to a larger space where I had my own room! Tropical Breeze Resort provided everything we needed! So convenient to walk to restaurants and shops. Best part was the short walk to the beach. Met so many great people! "
Jennifer 6-night trip
Posted 16 hours ago
Tropical Breeze Resort