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Aug 15 - Aug 17
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Vacation Homes in Windley Key

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
Relax in this serene beachside retreat with an outdoor space featuring a wicker table and chairs.

Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25

10.0 out of 10, Exceptional, (84)
"Everything just great except need better vaccum"
Oceanfront 165ft beach-Dock-Heated pool-4K sq.ft 4 bed/5 bath-Next avail 8.9.25
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Beach nearby, sun loungers, beach towels

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

9.6 out of 10, Exceptional, (35)
"Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. "
The price is ￥10,631
￥40,481 total
includes taxes & fees
Aug 21 - Aug 22
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Relax by the ocean with a clear view, lounge chairs, and a curved pool surrounded by lush greenery.

OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards

10.0 out of 10, Exceptional, (183)
"We had such a nice time at the Windley Cottage. The owners effectively communicated information about the home and check in before the stay, making arrival very easy. The home was very clean and had everything that we needed. The Anglers Reef area was nice and quiet. We enjoyed walks to the docks, kayaking, and swimming in the pool. We absolutely loved Islamorada and hope to visit again!"
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Relax by the pool surrounded by palm trees and lounge chairs.

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (18)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Florida Keys Townhouse For Rent 2/2
Relax under the shade of thatched-roof structures, surrounded by sandy ground and natural rocks.

Florida Keys Townhouse For Rent 2/2

9.4 out of 10, Exceptional, (171)
"We used this as accommodation to explore the keys for 6days and it did not disappoint. Very accurate description of the house. Nice, clean and tidy. Thank you"
Florida Keys Townhouse For Rent 2/2
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Relax by the serene waterfront, where a dock invites you to unwind with a meal or a moment of tranquility.

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (117)
"Best sunrise site."
The price is ￥22,690
￥61,356 total
includes taxes & fees
Aug 25 - Aug 26
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Enjoy ocean views from the resort's two-story buildings with balconies.

OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars

10.0 out of 10, Exceptional, (193)
"Great location. Beautiful, comfortable accommodations. Would absolutely return. "
OCEAN VIEW ANGLERS REEF - POOL, DOCK, BEACH. Walk or Bike to local food + bars
Charming Home in Key Largo
Kitchen features a central island with a countertop, surrounded by cabinetry and a refrigerator, microwave, and oven.

Charming Home in Key Largo

9.8 out of 10, Exceptional, (23)
"Amazing spot in the Keys. Stayed there the weekend for a wedding in Tavernier and was close to everything we needed. Would definitely stay here again when I come back. "
The price is ￥21,421
￥60,756 total
includes taxes & fees
Aug 13 - Aug 14
Charming Home in Key Largo
Waterfront Tiny House w Pool, Beach, and Boat Dock
Marina

Waterfront Tiny House w Pool, Beach, and Boat Dock

9.6 out of 10, Exceptional, (57)
"My wife and I stayed here for our honeymoon , and we were absolutely thrilled with everything. We loved that the house had a bunch of mini splits to keep it nice and chilly. We also loved that the house was very clean and well kept. The tiki hut on the water with the tv and great lighting at night makes a perfect place to relax at the end of a fun filled day. All around this was a fantastic place to stay!"
The price is ￥17,137
￥54,227 total
includes taxes & fees
Aug 21 - Aug 22
Waterfront Tiny House w Pool, Beach, and Boat Dock
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
Terrace/patio

NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony

10.0 out of 10, Exceptional, (1)
"This property was amazing basically brand new definitely recommend "
NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Relax by the pool under the stars, surrounded by lush trees and a thatched-roof structure.

7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks

10.0 out of 10, Exceptional, (55)
"We have stayed in one of this Hosts properties for 5 years in a row. Always clean, always great communication and we always have a great time. We highly recommend."
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Relax on the beach with lounge chairs and enjoy the tranquil atmosphere.

Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball

9.8 out of 10, Exceptional, (102)
"beautiful and quite neighborhood. "
Waterfront, saltwater lagoon, 2 pools, ocean access, marina, tennis, pickleball
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
Relax in a shaded beachside haven with a thatched-roof structure, comfortable seating, and stunning ocean views.

Beautiful Key Largo Town Home Fully Renovated Top to Bottom

9.8 out of 10, Exceptional, (163)
"The porperty had everything we needed for a great family spring break. The kids especially enjoyed trips to the jetty on the golf cart!"
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Relax by the pool surrounded by lush greenery and palm trees, with lounge chairs and umbrellas nearby.

New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities

2.5 star property
10.0 out of 10, Exceptional, (18)
"This condo and the club is awesome. The pool is wonderful. We loved everything about or stay would come back! "
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Relax by the central pool surrounded by lush greenery and palm trees, with sun loungers and umbrellas at your disposal.

Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!

10.0 out of 10, Exceptional, (8)
"We stayed at this property for our spring break trip and thoroughly enjoyed our stay. The home was clean, comfortable, and well-equipped with everything we needed. The location was great—close to local attractions yet peaceful enough for a relaxing getaway. The host was responsive and accommodating, making the entire experience seamless. We would definitely stay here again!"
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
Relax by the resort's pool surrounded by lush greenery and comfortable lounge chairs.

Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool

9.8 out of 10, Exceptional, (93)
"This is the best location we have stayed at in Islamorada. The community was safe and quiet, plenty to do right on site with swimming, private beach, kayaks and paddleboards, fishing off dock. We saw manatees most days in the marina. The house is exactly as listed, the owners were quick to respond and fix any issues we had. Would definitely rent again! "
Single Family Home In Angler's Reef Gated Community, Beaches,Marina,Heated Pool
NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
Enjoy a beach view from the large windows in this room, featuring a seating area with a sofa and armchairs.

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private

NEW! Stunning 2-acre Oceanfront Estate with Private Pool ~ Beach. Very private
611 Mariners Club Key Largo | 4 Bed, 4 Bath
Relax by the pool surrounded by palm trees and enjoy the serene atmosphere.

611 Mariners Club Key Largo | 4 Bed, 4 Bath

9.0 out of 10, Wonderful, (96)
"The unit was set up perfect for my family as well as my brother-in-law‘s for a family wedding in Key Largo. The pools were beautiful. The property was well maintained and we had a wonderful time. "
611 Mariners Club Key Largo | 4 Bed, 4 Bath
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Relax by the pool surrounded by lush tropical vegetation and a marina view.

Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker

10.0 out of 10, Exceptional, (38)
"Was a nice property and pleasant enough for our stay."
The price is ￥105,782
￥189,012 total
includes taxes & fees
Aug 10 - Aug 11
Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker
Keys Relaxing Getaway
Property grounds

Keys Relaxing Getaway

10.0 out of 10, Exceptional, (56)
"Beautiful,clean, great location"
Keys Relaxing Getaway
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 Windley Key Hotel Reviews

Reefhouse Resort & Marina

Reefhouse Resort & Marina

10/10 Excellent
"Great service "
Yanko 2-night trip
Posted 15 hours ago
Reefhouse Resort & Marina