Legacy Trail Vacation Rentals from $147: Search Short-Term Rentals

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Vacation Rentals in Legacy Trail

Enjoy cooking in this well-lit kitchen with a stainless steel range, sink, and coffee maker.

"It was perfect for my family of 4 for our beach vacation!!"

$322 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Enjoy a serene beach experience with access to the calm sea.

$219 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Enjoy a tranquil outdoor space with a clear view of the water, surrounded by tall palm trees and a grassy area, perfect for outdoor dining or cooking.

"Everything was great!"

$292 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Surrounded by lush trees and a manicured lawn, this serene outdoor space invites relaxation.

"The bedrooms and bathrooms were spacious and also the closets. The kitchen was well-equipped. Overall a very comfortable and safe place to stay."

$372 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel stove, and oven.

"The space was as advertised, clean and just the right size for us. Despite colder than normal temperatures, we had a great getaway and really enjoyed the hot tub."

$232 nightly

Aug 6 - Aug 7

Total includes taxes and fees

Relax in this stylish living room with a flat-screen TV, comfortable sofa, and a large potted plant.

"Amazing place and the host was awesome to work with and very accommodating! Highly recommend the area!"

$236 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Relax by the pool surrounded by lush tropical plants and palm trees.

"Very accommodating, very helpful , great communication, quickly responded to our needs."

$324 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Enjoy meals in the kitchen with an oven and dining area featuring a wooden table and chairs.

"Would highly recommend for a one or two night stay"

$312 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Relax in this stylish living area with a sofa, chairs, and a dining table, featuring a large painting of peacocks and a mounted TV.

"It was good! "

$423 nightly

Jul 26 - Jul 27

Total includes taxes and fees

Relax on the beach with lounge chairs and umbrellas scattered across the sand.

"Looking forward to staying there again."

$399 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Kitchen features a range hood above the stove, white cabinetry, and stainless steel appliances.

"We really enjoyed our stay at this cozy beach house. It was exceptionally clean and well stocked. A 5-6 minute drive had us on the beach. Would definitely stay again!"

$310 nightly

Jul 23 - Jul 24

Total includes taxes and fees

House, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster

$380 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Situated on the beach, this lifeguard station offers a convenient spot to watch over the clear waters.

"Loved our stay! "

$320 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Relax on the balcony with a view of the marina, surrounded by boats and the serene water.

"Awesome spot"

$186 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Relax in style with a comfortable seating area, barbecue grill, and ample shade options.

"Our stay here was just perfect - great location, everything we needed, Bryce left very good instructions for anything that we might have needed (we didn’t 😊), and very comfortable! We were close to everything but felt like we had our own little private place too. Will definitely come back here. "

$135 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Relax on the patio surrounded by lush greenery and enjoy the serene atmosphere.

"Very comfortable and perfect location to the airport! "

$175 nightly

Jul 28 - Jul 29

Total includes taxes and fees

Cozy cabin-style lodging with a central seating area, kitchenette, and lofted sleeping area.

"We enjoyed the stay and it worked well. "

$174 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Walk along the beach to a charming thatched-roof shelter.

"This is our second time staying at the Silver Sands. Very clean, nice people, nice amenities. "

$259 nightly

Jul 24 - Jul 25

Total includes taxes and fees

Relax by the pool surrounded by lush greenery and palm trees, with a clear view of the surrounding landscape.

"If you're looking for near beach (10 minutes) with private pool this is good spot. Also very convenient to grocery stores and many other necessities. "

$555 nightly

Aug 7 - Aug 8

Total includes taxes and fees

Relax on the beach with comfortable seating and lush surroundings.

"We had a great stay in this house, it was super comfortable and very well equipped. Would definitely stay again if we are in the area."

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Top Legacy Trail Hotel Reviews

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"Great place i loved it. "

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"This was my first time staying at this hotel. On the first day, the bathtub was clogged, but the staff acted quickly and switched us to a different room right away. Other than that, everything was great. The staff were incredibly friendly and helpful, always checking in to see if we needed anything. The beach, restaurant, and shops were all very close by, which made everything super convenient. I’ll definitely be coming back in the future. Thank you! 😊"

Siesta Key Beach Resort and Suites

10/10 Excellent

"The resort truly surprised us with the location & amenities. The room was small & clean, bed & pillows comfortable, they had a fridge, microwave, coffee maker with quite a few coffees & creamers. Shampoo, Conditioners, lotions & soaps in the bathroom were great. They had 2 complimentary bottles of water, some pretzels, popcorn which was a nice touch. Additionally & most appreciated was the 2 nice beach chairs and soft-sided cooler to use for the beach! The Big Tiki was great, they offered a couple of bogo coupons which we took full advantage of & then some. Minor downsides & not big at all, the pool was extremely warm & not refreshing, it was hot so it’s hard to regulate so it may not be helped but felt like they filter the same water through vs some new fresh water. That may also just be to save water which we can also appreciate. The pool area was nice & clean, with shower & shade, restrooms, plenty of loungers. They have a great towel replacement system but our towels weren’t picked up or replaced even though we put them out prior to the set times. Only happened once & just reused the towels that were damp. They dried out quickly in the heat. The last was the guy using the leaf blower between 7-7:30 in the morning on Saturday right outside the rooms …we were already stirring but felt for the families on the first level where it must have been louder. Again, these are all small & won’t stop us from going back or referring to others! Already looking for our next visit!"

Find out more about Legacy Trail

Everything you need to know about Legacy Trail vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Legacy Trail vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Legacy Trail vacation 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 low season months. For more hustle and bustle, you may prefer to visit Legacy Trail in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $147 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Legacy Trail rentals

At Expedia, we put the best Legacy Trail vacation 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 vacation.

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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Vacation Rentals in Legacy Trail

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

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!

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

W Bradenton Country Club Estates, 2 bed, 2Bath 7miles to Beaches

W Bradenton Country Club Estates, 2 bed, 2Bath 7miles to Beaches

Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!

Renovated Quiet Venice Pool + Hot Tub Oasis-1/1!

Charming home near Anna Maria Island with Jacuzzi

Charming home near Anna Maria Island with Jacuzzi

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

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

Modern 2 Bedroom Farmhouse

Modern 2 Bedroom Farmhouse

Bradenton Breeze

Bradenton Breeze

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

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

Newly renovated cozy beach house.

Newly renovated cozy beach house.

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

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

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

Gorgeous Pool house 5 min from the beach, shopping and restaurants I

RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette

RAMADA SARASOTA CONDO HOTEL#407 Waterfront Balcony, King Bed, Pool, Kitchenette

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

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

Casa Azul 2Bed/1Bath

Casa Azul 2Bed/1Bath

Tiny House Yellow Lifeguard Stand- pet friendly

Tiny House Yellow Lifeguard Stand- pet friendly

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

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

Sunny Skies: Modern 2-Bedroom Home with Pool Near Bradenton Beach Awaits You!

Sunny Skies: Modern 2-Bedroom Home with Pool Near Bradenton Beach Awaits You!

Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

Beautiful Nokomis Beach Cottage. Walk to Beach w/Tranquil & Private Patio

Top Legacy Trail Hotel Reviews

DoubleTree by Hilton Sarasota Bradenton Airport

Find out more about Legacy Trail

Find out more about Legacy Trail

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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