Windley Key Vacation Rentals

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Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Browse Select Windley Key Vacation Homes

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Outdoor pool, a heated pool

Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.6 out of 10, Exceptional, (58)
"The property is central location in Islamorada, best location....The outdoor area is perfect,pool heated very enjoyable.. great neighborhood..Friendly Host JoAnn is amazing, and prompt response, a delightful person, and a wonderful host!"
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Charming Home in Key Largo
Fridge, microwave, oven, stovetop

Charming Home in Key Largo

9.8 out of 10, Exceptional, (25)
"loved it!!"
The price is CA $181
CA $543 total
includes taxes & fees
Aug 18 - Aug 19
Charming Home in Key Largo
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Marina

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

9.4 out of 10, Exceptional, (72)
"The house is great, tidy little spot to start all your Keys adventures from!"
The price is CA $140
CA $478 total
includes taxes & fees
Aug 14 - Aug 15
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
New Mariners Club Listing, Preferred Partner, Great Location, Epic Amenities
Outdoor pool, a heated pool

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

2.5 star property
10.0 out of 10, Exceptional, (19)
"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
208 Mariners Club Key Largo | 3 Bed, 3 Bath
A heated pool

208 Mariners Club Key Largo | 3 Bed, 3 Bath

9.8 out of 10, Exceptional, (89)
"We had a Wonderful time! There was plenty of space for our family of five. We had a few minor issues with ants, but it did not impact our comfortable stay. We loved the pool and Pickleball court! Would highly recommend. "
208 Mariners Club Key Largo | 3 Bed, 3 Bath
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing
Outdoor pool, a heated pool

Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing

10.0 out of 10, Exceptional, (1)
"Beautiful property with a lot of space. Very well stocked with more than what you even think you need. Mariners Club is very nice with two great pools, a game room, marina, and pickleball courts. Only thing to note is there’s no beach access if that’s what you are looking for."
Mariners Club Unit 904, Brand New Completely Remodeled Preferred Partner Listing
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Exterior

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (66)
"Such a great, gated location with access to a variety of amenities. "
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Outdoor pool, a heated pool

Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball

9.6 out of 10, Exceptional, (19)
"Clean , beautiful location and pools . "
Mariners Club Townhouse, Epic Amenities, Tennis & Indoor Pickleball
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Outdoor dining

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (118)
"Best sunrise site."
The price is CA $195
CA $547 total
includes taxes & fees
Aug 14 - Aug 15
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Catch your last summer glow at Mariners Club 606 w resort style amenities & more
Pool

Catch your last summer glow at Mariners Club 606 w resort style amenities & more

10.0 out of 10, Exceptional, (138)
"Nice location with lots of restaurant choices, pools and especially the Grotto were awesome, Tarpon feeding was our favorite nearby activity."
The price is CA $412
CA $1,230 total
includes taxes & fees
Aug 17 - Aug 18
Catch your last summer glow at Mariners Club 606 w resort style amenities & more
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 CA $171
CA $519 total
includes taxes & fees
Sep 3 - Sep 4
Waterfront Tiny House w Pool, Beach, and Boat Dock
VOTED BEST KEY LARGO VACATION RENTAL
Terrace/patio

VOTED BEST KEY LARGO VACATION RENTAL

10.0 out of 10, Exceptional, (81)
"We had a great stay! We loved having kayaks, snorkels, a lagoon and the ocean and everything nearby. We loved feeding the fish on the property. The kitchen is well stocked with everything we needed for making meals. Nice restaurants nearby! Thanks for meeting us, Norman - that was very helpful!!"
VOTED BEST KEY LARGO VACATION RENTAL
7 Bedroom with Dockage, Pool, Firepit, Paddle Boards & Kayaks
Outdoor pool, a heated pool

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
Beautiful Key Largo Town Home Fully Renovated Top to Bottom
Property grounds

Beautiful Key Largo Town Home Fully Renovated Top to Bottom

9.8 out of 10, Exceptional, (164)
"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
Resort-Style Living at Mariner's Club – Steps from Pools, Marina, & Ocean Views!
Outdoor pool, a heated pool

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!
PRIVATE WATERFRONT HOUSE DOCK 4KAYAKS 2SUP BOARD GOLF CART
Outdoor spa tub

PRIVATE WATERFRONT HOUSE DOCK 4KAYAKS 2SUP BOARD GOLF CART

10.0 out of 10, Exceptional, (138)
"We loved this house! Plenty of room, wonderful location. Super clean and the outdoor space was awesome! Hot tub, BBQ and plenty of toys to enjoy the lagoon❤️"
The price is CA $482
CA $1,221 total
includes taxes & fees
Aug 17 - Aug 18
PRIVATE WATERFRONT HOUSE DOCK 4KAYAKS 2SUP BOARD GOLF CART
611 Mariners Club Key Largo | 4 Bed, 4 Bath
A heated pool

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
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
A heated pool

Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!

9.8 out of 10, Exceptional, (153)
"Great place! Exactly as described."
Islamorada Anglers Reef! “Sandbar Bungalow Villa" AMAZING! Middle row location!
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Outdoor pool, a heated pool

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools

9.6 out of 10, Exceptional, (8)
"Me my wife and 2 kids 18 & 19 had a great time. Loved the lagoon and the local places to eat and drink. "
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
A heated pool

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

10.0 out of 10, Exceptional, (185)
"Lodgings first rate. Boat access to Mahi and Grouper catches."
OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards
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

Amara Cay Resort

Amara Cay Resort

10/10 Excellent
"Top notch all around. "
David 2-night trip
Posted 4 hours ago
Amara Cay Resort