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Featured Condo Rentals in Legacy Trail

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1123)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
Captiva Beach Resort

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (11)
"Nic place to stay and enjoy the area"
The price is AU$845
includes taxes & fees
25 Aug - 26 Aug
Chadwick Cove Resort & Marina

Cozy Condo With Heated Pool

9.6 out of 10, Exceptional, (35)
"Property and condo owner good. Condo AC did not work when we arrived. Once we could finally reach owner they did a good job to promptly get an AC Tech to repair. Using the VRBO site was not very user friendly. Was hard to navigate VRBO web site and even when it did work. "
Cozy Condo With Heated Pool

Cozy beach house! Just steps away from the world-class Manasota beach

3.5 star property
9.8 out of 10, Exceptional, (6)
"Great place. "
Cozy beach house! Just steps away from the world-class Manasota beach

Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA

8.8 out of 10, Excellent, (84)
"Gorgeous location, the beach was exceptional and the area was quiet and felt secluded. The condo was a bit shabby but clean and had everything we needed. "
The price is AU$497
includes taxes & fees
21 Aug - 22 Aug
Oceanfront Bliss - The Beach on Longboat Key #106 Resort by RVA

Anna Maria Sunsets - studio

9.0 out of 10, Wonderful, (217)
" Very clean great location and property owner very nice and understanding thank you for everything "
The price is AU$331
includes taxes & fees
21 Aug - 22 Aug
Anna Maria Sunsets - studio

Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

9.8 out of 10, Exceptional, (95)
"Lovely unit and the perfect location. Short walk to the beach and easy to get to the shopping/eating areas. "
The price is AU$639
includes taxes & fees
22 Aug - 23 Aug
Clean, modern and newly RENOVATED condo on US #1 Private Siesta Key Beach

2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA

8.6 out of 10, Excellent, (41)
"Beautiful place with a private beach and a really nice clean condo. Had everything we needed for a relaxing weekend. Will definitely come back! Thank you."
The price is AU$624
includes taxes & fees
21 Aug - 22 Aug
2nd Floor Retreat Overlooking the Pool & Gulf Silver Sands #251 Resort by RVA

*Charming 2bed 2 bath 6 mins from IMG*

9.6 out of 10, Exceptional, (21)
"Great place, spacious for 6 adults, clean, comfortable, organized with all the amenities one would need. Everything was simple from check in to check out. The queen-size air mattress fits seamlessly in the living room's common area and comes equipped with all necessary bedding to ensure a comfortable and restful experience.​ I would stay again!"
The price is AU$546
includes taxes & fees
21 Aug - 22 Aug
*Charming 2bed 2 bath 6 mins from IMG*

Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

9.8 out of 10, Exceptional, (59)
"Perfect accommodation "
The price is AU$597
includes taxes & fees
23 Aug - 24 Aug
Fantastic Shorewalk Vacation 2 bed/2 bath condo/Lake view/close to IMG, beaches

Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

10.0 out of 10, Exceptional, (113)
"Great place to stay. Accomodations were very good."
The price is AU$474
includes taxes & fees
21 Aug - 22 Aug
Lavish Waterfront Condo! Heated Pools~Lanai~WiFi. By IMG~Beaches~AMI~Restaurants

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

9.4 out of 10, Exceptional, (130)
"Loved how close it is to siesta key beach"
The price is AU$568
includes taxes & fees
11 Sept - 12 Sept
Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

9.4 out of 10, Exceptional, (95)
"A very pleasant and comfortable experience in a beautiful location."
The price is AU$668
includes taxes & fees
21 Aug - 22 Aug
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Condo with a View 1: Oceanfront!

10.0 out of 10, Exceptional, (115)
"Great location..Everyday"
The price is AU$607
includes taxes & fees
2 Sept - 3 Sept
Condo with a View 1: Oceanfront!

Casa Azul 2Bed/1Bath

9.4 out of 10, Exceptional, (63)
"Very comfortable and perfect location to the airport! "
The price is AU$304
includes taxes & fees
21 Aug - 22 Aug
Casa Azul 2Bed/1Bath

Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA

8.2 out of 10, Very good, (69)
"We liked the property and the location. We were not expecting to have a mini fridge. The mini fridge limited what we could keep in the room. The beach was quiet. Still lots of devastation from the hurricane. We visited shops and some had been open just a couple of months. We did enjoy our trip. If you visit this area try to support these shops and businesses. "
Large Studio on Gulf! Cabana Beach Club #5B Longboat Key-Steps to Sand by RVA

Best views of the beach from your balcony Unit 301

9.8 out of 10, Exceptional, (85)
"This condo is fantastic! The views are unbeatable. Great location for a family vacation. We would highly recommend it! "
The price is AU$589
includes taxes & fees
25 Aug - 26 Aug
Best views of the beach from your balcony Unit 301

POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

9.6 out of 10, Exceptional, (44)
"The location of the property could not have been better. A very short walk to the quietest beach on Siesta Key. The manager was very attentive when we called with a minor issue and had it resolved quickly. The property could use a pretty thorough cleaning of the baseboards and other nooks and crannies but overall it was pretty clean. We would stay again."
The price is AU$529
includes taxes & fees
2 Sept - 3 Sept
POOL VIEW Walk to beach King bed Heated pool DAILY WEEKLY SPECIALS villa 3

Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA

8.8 out of 10, Excellent, (42)
"Enjoyed our stay"
Sun, Sand & Silver Sands – Gulfside Resort Escape Unit #237 by RVA

Charming 1-bedroom, beachfront condo in marvelous Longboat Key

9.0 out of 10, Wonderful, (17)
"The property was great for our family, loved having a pool and beach access. Super simple especially with a toddler in tow."
The price is AU$651
includes taxes & fees
24 Aug - 25 Aug
Charming 1-bedroom, beachfront condo in marvelous Longboat Key
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