Legacy Trail Condo Rentals

Legacy Trail Condo Rentals
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Our top choices for Legacy Trail condo rentals

A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

A living room with a sofa, coffee table, and a dining area with chairs. There is a sign on the wall and a painting above the sofa.

A modern kitchen with a central island, white cabinetry, and a dining area with a table and chairs.

A beach scene with a hammock, palm trees, and the sun setting over the ocean.

1. A Beach Retreat

A Beach Retreat

2.5 star property

Casey Key

9.2 out of 10, Wonderful, (688 reviews)

9.2/10

Wonderful

(688 reviews)

"Great stay!!"

Genghis

The price is HK$1,446

HK$1,446

HK$1,634 total

includes taxes & fees

4 Nov - 5 Nov

A Beach Retreat

A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

A narrow concrete pathway flanked by lush tropical plants, leading to a wooden gate.

A modern kitchen with white cabinets, stainless steel appliances, and a marble countertop.

A beach with white sand, wooden beach chairs, and a clear blue sky.

2. Captiva Beach Resort

Captiva Beach Resort

3.0 star property

South Village

9.0 out of 10, Wonderful, (1,318 reviews)

9.0/10

Wonderful

(1,318 reviews)

"Clean room, beach access, easy parking, friendly staff"

Karla

The price is HK$1,225

HK$1,225

HK$1,517 total

includes taxes & fees

11 Oct - 12 Oct

Captiva Beach Resort

A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

A beachside bar with a thatched roof, stools, and a sign reading "TO GO".

A living room with a sofa, a television, a coffee table, and a kitchenette in the background.

A pool area with lounge chairs and a covered seating area.

3. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

South Village

9.6 out of 10, Exceptional, (49 reviews)

9.6/10

Exceptional

(49 reviews)

"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "

maureen p.

The price is HK$754

HK$754

HK$1,979 total

includes taxes & fees

11 Oct - 12 Oct

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

A covered outdoor deck with a table and chairs, overlooking a body of water and palm trees.

A modern kitchen with white cabinetry, a built-in dishwasher, and a coffee maker.

A view through a window with a clear sky, a body of water, a dock, and some greenery.

4. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

4.0 star property

Manasota Key

8.8 out of 10, Excellent, (30 reviews)

8.8/10

Excellent

(30 reviews)

"Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!"

Niovys

The price is HK$1,261

HK$1,261

HK$4,944 total

includes taxes & fees

11 Oct - 12 Oct

Chadwick Cove Resort & Marina

A lifeguard tower on a beach with clear blue water and a palm tree in the foreground.

A spacious library with bookshelves, a dining area with chairs, and a large potted plant.

A modern living room with a glass dining table, two black sofas, a coffee table, and a ceiling fan.

5. Lake-view Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Lake-view Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Bradenton

9.8 out of 10, Exceptional, (126 reviews)

9.8/10

Exceptional

(126 reviews)

"We loved the property, large pool & access to activities. "

Mary Beth M.

The price is HK$848

HK$848

HK$2,398 total

includes taxes & fees

15 Oct - 16 Oct

Lake-view Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

A modern kitchen with grey cabinets, stainless steel appliances, and a herringbone tile backsplash.

A waterfront hotel with a marina, palm trees, and high-rise buildings in the background.

A modern building with a flat roof, large windows, and a covered outdoor area with seating.

6. Fully renovated Siesta Key Condo | Walk to Beach | Pool | Perfect Location in SK Village

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

Siesta Key Village

9.4 out of 10, Exceptional, (92 reviews)

9.4/10

Exceptional

(92 reviews)

"Fantastic stay for our family’s 4th of July getaway! The condo was perfect—an easy walk to both the beach and town, which made everything super convenient. The pool was clean and refreshing, and we loved having the outdoor picnic tables for meals and games. Beds were very comfortable, and everyone slept great. Would happily stay here again!"

Kim S.

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

A wooden pathway leading to a beach with lush greenery on either side.

A modern living room with a sofa, a coffee table, a TV mounted on the wall, a ceiling fan, and a sliding glass door leading to an outdoor area.

A pool with a view of the ocean, surrounded by palm trees and lounge chairs.

A modern hotel room with a bed, a desk, a chair, a kitchenette, and a ceiling fan.

7. Oceanfront Bliss–Longboat Key Beach 106 by RVA

Oceanfront Bliss–Longboat Key Beach 106 by RVA

Longboat Key

8.8 out of 10, Excellent, (108 reviews)

8.8/10

Excellent

(108 reviews)

"It was a great location. It had a nice pool area, plenty of beach chairs and beach goodies to use."

Laurie L.

The price is HK$1,020

HK$1,020

HK$2,379 total

includes taxes & fees

12 Oct - 13 Oct

Oceanfront Bliss–Longboat Key Beach 106 by RVA

A sign reading "Shorewalk" with a landscaped area featuring bushes and a palm tree.

A living room with a sofa, coffee table, TV, and a ceiling fan.

A bedroom with a bed, a TV, a sofa, and a window with a view of greenery.

An aerial view of a residential area with a swimming pool, a bridge, and a tennis court.

8. 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, (74 reviews)

9.8/10

Exceptional

(74 reviews)

"The condo was in a great location for our family and it was very clean."

Nicole W.

The price is HK$1,052

HK$1,052

HK$3,003 total

includes taxes & fees

11 Oct - 12 Oct

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

A modern kitchen with white cabinetry, a dishwasher, and a stove. There is a dining area with a chair and a table visible through an open door.

A clean, modern bathroom with a white vanity, a mirror with a wooden frame, and a window with a view of the outside.

9. Heart of Village: Dog-Friendly w/ Pool & Parking

Heart of Village: Dog-Friendly w/ Pool & Parking

Siesta Key Village

9.2 out of 10, Wonderful, (16 reviews)

9.2/10

Wonderful

(16 reviews)

"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."

Jeffrey B.

The price is HK$1,099

HK$1,099

HK$3,098 total

includes taxes & fees

20 Oct - 21 Oct

Heart of Village: Dog-Friendly w/ Pool & Parking

A wooden pathway leading to a sandy beach with palm trees on either side.

A golf course with multiple water hazards, surrounded by buildings and a beach.

A modern living room with a glass coffee table, a sofa with a patterned cushion, and a ceiling fan.

10. Resort Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Resort Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Bradenton

9.8 out of 10, Exceptional, (161 reviews)

9.8/10

Exceptional

(161 reviews)

"Good location, good communication with host, very clean. Very easy check in and check out process "

Cathleen R.

The price is HK$812

HK$812

HK$2,358 total

includes taxes & fees

18 Oct - 19 Oct

Resort Corner Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

A street with a yellow building with a balcony, a storefront with a sign, and a tree with red flowers.

A gym with weightlifting equipment, benches, and a sign for AMPEC FITNESS.

11. Bright Lake-View Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Bright Lake-View Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

Bradenton

10.0 out of 10, Exceptional, (132 reviews)

10/10

Exceptional

(132 reviews)

"It was a perfect location, looked exactly like the pictures and the host did everything to make our stay great!"

Martha B.

The price is HK$800

HK$800

HK$2,345 total

includes taxes & fees

12 Oct - 13 Oct

Bright Lake-View Condo Near Anna Maria Island & IMG with Heated Pools & Hot Tubs

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, a stove, and a coffee maker.

A beach with a wooden picnic table, palm trees, and a clear blue sea.

A modern hotel room with a bed, a TV displaying a beach scene, a dining area, and a small table with a decorative item.

12. Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

Siesta Key

9.2 out of 10, Wonderful, (145 reviews)

9.2/10

Wonderful

(145 reviews)

"We loved it!"

John S.

The price is HK$1,447

HK$1,447

HK$2,408 total

includes taxes & fees

11 Oct - 12 Oct

Spacious Renovated 1 Bedroom Siesta Key Beachside Vacation Rental Getaway

A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

A sign for 'The Beach Club' with a vacancy indicator.

A multi-story hotel with balconies, palm trees, and a parking area.

A pool area with palm trees, a small pool, and a wooden fence.

13. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA

South Village

8.8 out of 10, Excellent, (57 reviews)

8.8/10

Excellent

(57 reviews)

"Peaceful getaway. Throughly enjoyed the stay. "

Anonymous traveller

The price is HK$1,342

HK$1,342

HK$2,792 total

includes taxes & fees

11 Oct - 12 Oct

Romantic Getaway Beach Club Siesta 202B by RVA

A beach with clear turquoise water and a sandy shore.

A golf course with a view of the ocean, palm trees, and a building with a red roof.

A well-maintained lawn with a shuffleboard court, palm trees, and a gazebo overlooking a beach.

A coastal hotel with multiple buildings, a sandy beach, and a view of the sea and islands.

14. 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, (93 reviews)

9.8/10

Exceptional

(93 reviews)

"The location of the condo is 10 out of 10. The views and beach access cannot be beat. We enjoyed the space and appreciated the small but functional kitchen. We even found some beach supplies and an umbrella in the closet! This is a very great space and location. We will be back!"

Anthony B.

The price is HK$1,298

HK$1,298

HK$3,093 total

includes taxes & fees

14 Oct - 15 Oct

Best views of the beach from your balcony Unit 301

A beach path leading to the sea with grass on either side.

A modern living room with a sofa, coffee table, and TV, a balcony with outdoor furniture, and a ceiling fan.

A modern kitchen with white cabinets, a microwave, stove, and refrigerator. There is a seating area with a brown chair and a view of the outdoors through a glass door.

A living room with a sofa, two side tables with lamps, a coffee table, and a view through a glass door.

15. Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”

Casey Key

9.6 out of 10, Exceptional, (37 reviews)

9.6/10

Exceptional

(37 reviews)

"Amazing view and beach access, really great stay."

Evan T.

The price is HK$1,214

HK$1,214

HK$3,008 total

includes taxes & fees

13 Oct - 14 Oct

Jetties Pointe Cottage #5 - 408 “Casey Key”

A room with a large window overlooking a beach, a round table with chairs, and a wicker chair with a cushion.

A beachfront property with a swimming pool, multiple balconies, and lush greenery.

A spacious living room with a large window overlooking the ocean, a ceiling fan, and a cozy seating area with a sofa and chairs.

16. The Beach on Longboat Key #227 Resort by RVA

The Beach on Longboat Key #227 Resort by RVA

Longboat Key

9.2 out of 10, Wonderful, (89 reviews)

9.2/10

Wonderful

(89 reviews)

"Great location and great views!"

Mark H.

The price is HK$1,468

HK$1,468

HK$2,999 total

includes taxes & fees

18 Oct - 19 Oct

The Beach on Longboat Key #227 Resort by RVA

A beach with clear blue water and a sandy shore, framed by green foliage.

A beachfront hotel with palm trees, a sandy beach, and a white building with multiple windows and balconies.

A sign for 'The Beach at Longboat Key' with the address '3465'.

An outdoor patio with blue chairs and a table, a blue umbrella, and a view of the beach and ocean.

17. Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

Longboat Key

8.2 out of 10, Very good, (25 reviews)

8.2/10

Very good

(25 reviews)

"Excellent place to stay. "

Hadley R.

The price is HK$1,570

HK$1,570

HK$2,766 total

includes taxes & fees

18 Oct - 19 Oct

Beachfront- Longboat Key efficiency condo w/ king size bed, steps to sand.

An aerial view of a beach with a clear turquoise sea, a sandy shore, and a dense residential area with houses and parked cars.

18. Sleek Remodeled 2BR/2BA Condo with Designer Master Suite & Open Layout

Sleek Remodeled 2BR/2BA Condo with Designer Master Suite & Open Layout

Bradenton

10.0 out of 10, Exceptional, (10 reviews)

10/10

Exceptional

(10 reviews)

"Just as advertised with good location and service!"

TOM

The price is HK$957

HK$957

HK$2,345 total

includes taxes & fees

11 Oct - 12 Oct

Sleek Remodeled 2BR/2BA Condo with Designer Master Suite & Open Layout

A balcony with a view of a beach, a pool, and palm trees.

A beach with clear skies, palm trees, and a sandy shore.

A dessert with fruit on a table with a view of a beach and palm trees.

19. Direct Oceanview: Open October 26th - 29th!

Direct Oceanview: Open October 26th - 29th!

Longboat Key

10.0 out of 10, Exceptional, (135 reviews)

10/10

Exceptional

(135 reviews)

"Great view of the beach and could watch sunset right from balcony, host was awesome, she gave all.kinds of suggestions and was very quick to respond to any questions we had. Would recommend this unit to anyone. They have beach supplies so you dont have to buy any of that. Longboat was very beautiful area."

Gina

The price is HK$1,766

HK$1,766

HK$3,308 total

includes taxes & fees

9 Nov - 10 Nov

Direct Oceanview: Open October 26th - 29th!

20. Modern Lake-View Condo Near Anna Maria Island & IMG ~ Heated Pools & Hot Tubs

Modern Lake-View Condo Near Anna Maria Island & IMG ~ Heated Pools & Hot Tubs

Bradenton

9.8 out of 10, Exceptional, (206 reviews)

9.8/10

Exceptional

(206 reviews)

"The apt was clean and very comfortable and the pool and hot tub were great! Parking perfect right in front and a short walk to tennis and pool. "

Cathleen T.

The price is HK$848

HK$848

HK$2,398 total

includes taxes & fees

19 Oct - 20 Oct

Modern Lake-View Condo Near Anna Maria Island & IMG ~ Heated Pools & Hot Tubs

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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