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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Legacy Trail condo rentals

Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is €491
includes taxes & fees
12 May - 13 May
Chadwick Cove Resort & Marina
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,250 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is €186
includes taxes & fees
12 May - 13 May
Captiva Beach Resort
Beachside One Bedroom Suite

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (631 reviews)
"Love this place"
United States
Marialis
The price is €190
includes taxes & fees
18 May - 19 May
A Beach Retreat
Beach nearby, sun-loungers, beach towels, snorkelling

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village

Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village
Siesta Key Village
9.4 out of 10, Exceptional, (81 reviews)
"This condo has been nicely appointed and has everything you need for a beach vacation. It's also in the village near all shops and eateries. "
United States
Abi-Gayil G.
Fully renovated Siesta Key Condo | Walk to Beach | Pool | Dog OK | Perfect Location in SK Village
On the beach

Drift & Dune – Longboat Beachfront #101 RVA

Drift & Dune – Longboat Beachfront #101 RVA
Longboat Key
8.6 out of 10, Excellent, (80 reviews)
"Check in and out was easy, the pool and condo were great, and the location was awesome!"
United States
Bailey B.
The price is €290
includes taxes & fees
13 May - 14 May
Drift & Dune – Longboat Beachfront #101 RVA
Fridge, microwave, oven, stovetop

Beach Condo with Pool Near Holmes Beach!

Beach Condo with Pool Near Holmes Beach!
Holmes Beach
9.0 out of 10, Wonderful, (40 reviews)
"Everything was as expected and the location is great."
United States
Thomas T.
The price is €501
includes taxes & fees
12 May - 13 May
Beach Condo with Pool Near Holmes Beach!
Beach nearby, beach towels

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs

Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
Bradenton
9.8 out of 10, Exceptional, (120 reviews)
"Perfect spot and host "
United States
Dee B.
The price is €260
includes taxes & fees
1 Jun - 2 Jun
Lakefront Condo · IMG Academy 5 Min · Anna Maria Island 15 Min· Pools & Hot Tubs
On the beach, sun-loungers, beach towels

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf

3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
Manasota Key
9.4 out of 10, Exceptional, (83 reviews)
"Beautiful condo!! The owner was very responsive and attentive. We will definitely recommend this place to anyone!"
United States
Kay C.
The price is €347
includes taxes & fees
13 May - 14 May
3 Bedroom- Beachfront Condo with Beautiful Views of the Gulf
On the beach

Beachfront Studio – Cabana #5B by RVA

Beachfront Studio – Cabana #5B by RVA
Longboat Key
8.2 out of 10, Very good, (78 reviews)
"The pool was disgusting, dirt and debris on the bottom and top so that was disappointing, while watching TV and sleeping a person actually opened up our porch door then the main door and just walked in and said they had booked the same room and had keys, what kind of place does not keep track of that and I'm not sure what the person was thinking the TV was on and it was up a little so I know they heard it from the outside but to get back to that place for allowing that to happen. He's lucky I...
United States
Joseph
The price is €265
includes taxes & fees
13 May - 14 May
Beachfront Studio – Cabana #5B by RVA
Pool

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC

Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
Bradenton Beach
10.0 out of 10, Exceptional, (20 reviews)
"Great location perfect room for 2 people. "
United States
Macey
The price is €299
includes taxes & fees
18 May - 19 May
Adorable 1-bedroom condo in beautiful Bradenton Beach with AC
On the beach

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA
Longboat Key
8.8 out of 10, Excellent, (98 reviews)
"Beautiful sunset view. "
United States
Rhonda V.
The price is €275
includes taxes & fees
16 May - 17 May
Oceanfront Bliss–Longboat Key Beach 106 by RVA
On the beach, beach umbrellas

1BR Beach Getaway – Silver Sands #254 by RVA

1BR Beach Getaway – Silver Sands #254 by RVA
Longboat Key
9.2 out of 10, Wonderful, (95 reviews)
"Great view, clean, beautiful!"
United States
Bethany
The price is €318
includes taxes & fees
13 May - 14 May
1BR Beach Getaway – Silver Sands #254 by RVA
Beach nearby

Best views of the beach from your balcony Unit 301

Best views of the beach from your balcony Unit 301
Longboat Key
9.8 out of 10, Exceptional, (89 reviews)
"Everything was great "
United States
kirt v.
The price is €350
includes taxes & fees
29 May - 30 May
Best views of the beach from your balcony Unit 301
Outdoor dining

Island Time: Open Wednesday, $225/nt + Fees!

Island Time: Open Wednesday, $225/nt + Fees!
Longboat Key
10.0 out of 10, Exceptional, (125 reviews)
"Great host! Amazing location. Loved the beach access and views! Highly recommended "
United States
Bonnie N.
The price is €363
includes taxes & fees
13 May - 14 May
Island Time: Open Wednesday, $225/nt + Fees!
On the beach, beach umbrellas

Silver Sands 1BR – Gulfside Comfort #255 by RVA

Silver Sands 1BR – Gulfside Comfort #255 by RVA
Longboat Key
9.0 out of 10, Wonderful, (87 reviews)
"Location #1. Clean #2"
United States
Eric C.
The price is €324
includes taxes & fees
12 May - 13 May
Silver Sands 1BR – Gulfside Comfort #255 by RVA
Beach nearby, sun-loungers, beach towels

Lovely Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs

Lovely Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs
Bradenton
10.0 out of 10, Exceptional, (128 reviews)
"Great place to stay"
United States
Tawnee H.
The price is €258
includes taxes & fees
24 May - 25 May
Lovely Condo! IMG Academy 5 Min · Anna Maria Island 15 Min · Pools & Hot Tubs
Outdoor pool, a heated pool

The Perfect Getaway with Private Beach Access

The Perfect Getaway with Private Beach Access
Cape Haze
9.8 out of 10, Exceptional, (20 reviews)
"Lovely and peaceful yet plenty of things to do in the area. Enjoyed our stay."
United States
sharon b.
The price is €453
includes taxes & fees
12 May - 13 May
The Perfect Getaway with Private Beach Access
Beach nearby, sun-loungers, beach towels, snorkelling

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear

Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Sarasota
9.8 out of 10, Exceptional, (17 reviews)
"Wonderful location Perfect for what we wanted in a quick escape. "
United States
Antonio
The price is €496
includes taxes & fees
25 May - 26 May
Manatee at Coastal Breeze | Stunning Bay Views | Walk to Beach | Dock Access | Fishing | Beach Gear
Property grounds

Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches

Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
Bradenton
9.8 out of 10, Exceptional, (70 reviews)
"Excellent stay. Great place that was nice, clean and quiet. "
United States
David S.
The price is €329
includes taxes & fees
12 May - 13 May
Peaceful Lakeview Condo • 2 Pools • Minutes to IMG & Beaches
On the beach, beach umbrellas

Relax at Gulf – Silver Sands Resort #232, Longboat

Relax at Gulf – Silver Sands Resort #232, Longboat
Longboat Key
9.2 out of 10, Wonderful, (79 reviews)
"Great beach access. Central location on the island. Not overcrowded. Ground floor unit was in good shape considering the hurricane in 2024.Bedroom could use blackout curtains (it gets bright in there in the AM) and the road noise was a bit loud."
United States
Mark G.
The price is €302
includes taxes & fees
12 May - 13 May
Relax at Gulf – Silver Sands Resort #232, Longboat
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent
"The hotel and staff were very very good. The breakfast was definitely less than what we expected and minimal tea options, and coffee was always empty. Pół area was clean and relaxing- we needed a late check out due to a car issue and staff was very accommodating. Beds were comfortable - our room was rather humid but the a/c worked great. Will return "
Maria 2-night trip
Posted 1 hour ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Legacy Trail

Legacy Trail Condo Rentals information

Number of reviews
2,915
Accommodation
432 Condo Rentals
Lowest Price
€186
Highest Price
€501

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