Search Vacation Homes in Legacy Trail

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Homes in Legacy Trail

Exterior
Siesta Key Island Rentals

Siesta Key Island Rentals

3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (51)
"Very nice place, we loved it. Great location. "
United States
Derrick
The price is ￥17,463
￥42,787 total
includes taxes & fees
Dec 1 - Dec 2
Siesta Key Island Rentals
Condo, Pool View | Private kitchen | Full-size fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is ￥19,625
￥53,585 total
includes taxes & fees
Nov 29 - Nov 30
Siesta Heron Suites & Villas
Beach nearby
Coastal duplex with private beach access & deck - dog-friendly

Coastal duplex with private beach access & deck - dog-friendly

Manasota Key
8.4 out of 10, Very Good, (12)
"Great place to stay. "
United States
Scott
The price is ￥13,898
￥57,845 total
includes taxes & fees
Dec 2 - Dec 3
Coastal duplex with private beach access & deck - dog-friendly
Property grounds
Old Floridian cottage in Historic Gulf Village

Old Floridian cottage in Historic Gulf Village

Olde Englewood Village
9.8 out of 10, Exceptional, (60)
"Very good, great location 👍👍"
United States
James M.
The price is ￥15,460
￥39,176 total
includes taxes & fees
Nov 28 - Nov 29
Old Floridian cottage in Historic Gulf Village
Fridge, microwave, oven, stovetop
8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear

South Venice
10.0 out of 10, Exceptional, (42)
"We had a wonderful time! The house was perfect and such a great location."
United States
Kellee N.
The price is ￥14,757
￥52,609 total
includes taxes & fees
Dec 16 - Dec 17
8 min to Beach ★ 5TV★Ice Hockey★ BBQ★ Bikes★Baby Gear ★Table Tennis ★Beach Gear
Property grounds
Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!

Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!

port charlotte
9.6 out of 10, Exceptional, (60)
"Peaceful - beautiful back yard area"
United States
Carmen R.
The price is ￥18,130
￥54,225 total
includes taxes & fees
Dec 1 - Dec 2
Tropical Home With Waterfall, HotTub, Fenced Yard, Beachy Lounge Area & Pets!
Property grounds
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!

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

2.0 star property
Sabal Harbour
10.0 out of 10, Exceptional, (19)
"Everything was great!"
United States
Lisa and Colin M.
The price is ￥18,973
￥53,375 total
includes taxes & fees
Nov 29 - Nov 30
Enjoy Coastal Townhome w/ sunset views! Near The Gulf’s most popular beaches!
Terrace/patio
The Hideaways at Point Pleasant (Palm Side)

The Hideaways at Point Pleasant (Palm Side)

Bradenton
10.0 out of 10, Exceptional, (168)
"perfect location and size for what we were looking for"
United States
michael w.
The price is ￥18,552
￥39,654 total
includes taxes & fees
Nov 29 - Nov 30
The Hideaways at Point Pleasant (Palm Side)
Smart TV, Netflix, streaming services
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach

Sarasota
9.4 out of 10, Exceptional, (16)
"Great location! Clean, easy to find and perfect amount of room. "
United States
Maribeliz G.
The price is ￥12,342
￥34,684 total
includes taxes & fees
Dec 1 - Dec 2
Small But Cute 1/1 In A Tropical Oasis, Close To Siesta Beach
Fridge, microwave, oven, stovetop
Newly renovated cozy beach house.

Newly renovated cozy beach house.

South Venice
10.0 out of 10, Exceptional, (6)
"The location was very convenient to the beach. It was a beautiful location."
United States
Carla C.
The price is ￥18,591
￥54,308 total
includes taxes & fees
Dec 10 - Dec 11
Newly renovated cozy beach house.
Fridge, microwave, oven, stovetop
Stylish house minutes from the beach

Stylish house minutes from the beach

South Venice
9.6 out of 10, Exceptional, (26)
"Great location and safe neighborhood. Definitely will stay again if available."
United States
Luis M.
The price is ￥16,725
￥53,950 total
includes taxes & fees
Nov 29 - Nov 30
Stylish house minutes from the beach
Fridge, microwave, oven, coffee/tea maker
Walk to Siesta key beach | Private Dock | Patio | Pool

Walk to Siesta key beach | Private Dock | Patio | Pool

Siesta Key Village
9.4 out of 10, Exceptional, (14)
"The place was clean and location was perfect! 2 blocks to the beach and 2 blocks to the village. It’s really great and helpful that they provided beach wagon, chairs and umbrella. "
United States
Amy
The price is ￥18,865
￥58,533 total
includes taxes & fees
Dec 1 - Dec 2
Walk to Siesta key beach | Private Dock | Patio | Pool
Property grounds
Beautiful home with very private heated pool minutes from the beach

Beautiful home with very private heated pool minutes from the beach

South Venice
9.8 out of 10, Exceptional, (30)
"Great vacation home. Loved the pool area and great location. The home had everything you need for cooking or going to the beach. Manasota beach was great to spend the day. Thanks again for your beautiful vacation home!"
United States
mickey m.
The price is ￥19,676
￥59,205 total
includes taxes & fees
Dec 2 - Dec 3
Beautiful home with very private heated pool minutes from the beach
Beach
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES

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

Sarasota
9.6 out of 10, Exceptional, (35)
"Great place, clean, fully stocked kitchen, very convenient location. Would definitely stay again."
United States
Nan G.
The price is ￥22,497
￥75,134 total
includes taxes & fees
Dec 4 - Dec 5
Extremely comfortable&clean VILLAS! Heated pool and Jacuzzi SUMMER SPECIAL RATES
Beach nearby, sun loungers, beach towels
Majestic Summer Sunsets just 50 steps to uncrowded beach & 2 King beds

Majestic Summer Sunsets just 50 steps to uncrowded beach & 2 King beds

Manasota Key
10.0 out of 10, Exceptional, (43)
"We had an amazing time and came home with lots of shells and shark teeth. Quiet neighborhood and steps to the beach. Would definitely stay here again. "
United States
Kari B.
The price is ￥27,568
￥63,684 total
includes taxes & fees
Dec 8 - Dec 9
Majestic Summer Sunsets just 50 steps to uncrowded beach & 2 King beds
Smart TV, stereo
Charming home near Anna Maria Island with Jacuzzi

Charming home near Anna Maria Island with Jacuzzi

2.0 star property
Bradenton
10.0 out of 10, Exceptional, (14)
"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"
United States
Kyle S.
The price is ￥18,973
￥43,615 total
includes taxes & fees
Nov 30 - Dec 1
Charming home near Anna Maria Island with Jacuzzi
Property grounds
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!

River District
10.0 out of 10, Exceptional, (58)
"We loved this cottage and will be back!"
United States
Brenda D.
The price is ￥20,379
￥59,844 total
includes taxes & fees
Nov 29 - Nov 30
1925 Historic Bradenton Bungalow, convenient to downtown and Anna Maria Island!
Fridge, microwave, oven, stovetop
Myakka River

Myakka River

Venice
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 "
United States
Ty
The price is ￥28,890
￥71,748 total
includes taxes & fees
Nov 28 - Nov 29
Myakka River
Beach nearby, sun loungers, beach towels
Single family home with private beach 120 steps away. Fish from our dock.

Single family home with private beach 120 steps away. Fish from our dock.

Manasota Key
9.8 out of 10, Exceptional, (115)
"Such a amazing week ... great location. The house is perfect for a family. House had eveething we needed. Found some awesome shells. A vacation to remember "
United States
Kim B.
The price is ￥27,406
￥63,490 total
includes taxes & fees
Dec 3 - Dec 4
Single family home with private beach 120 steps away. Fish from our dock.
Outdoor dining
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)
"Excellent for a family trip."
United States
RHEA
The price is ￥15,460
￥76,562 total
includes taxes & fees
Nov 29 - Nov 30
LAST MINUTE DEAL, Charming 2 Bed/2 Bath, FREE WiFi, Anna Maria Island Is Just Around The Corner or Stroll to Bay!
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.
View all properties
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

Compass Hotel by Margaritaville Anna Maria Sound

Compass Hotel by Margaritaville Anna Maria Sound

10/10 Excellent
"The manatees in the Marina were an awesome touch!"
Paul 1-night trip
Posted 2 days ago
Compass Hotel by Margaritaville Anna Maria Sound

Find out more about Legacy Trail

Legacy Trail Vacation Homes information

Number of reviews
815
Accommodation
1182 Vacation Homes
Lowest Price
￥34,684
Highest Price
￥76,562

Explore a world of travel with Expedia