Search Vacation Homes in Windley Key

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Windley Key vacation homes

Beach nearby, sun loungers, beach towels
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Key Largo
9.6 out of 10, Exceptional, (45)
"We absolutely loved it! "
United States
Emily B.
$305 nightly
The price is $339
Dec 15 - Dec 16
Total with taxes and fees
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Fridge, microwave, oven, stovetop
Charming Home in Key Largo

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (27)
"It was clean and a very nice place to stay. Plenty of room and awesome amenities."
United States
Eric M.
$410 nightly
The price is $455
Dec 28 - Dec 29
Total with taxes and fees
Charming Home in Key Largo
Marina
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

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

New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
Key Largo
9.6 out of 10, Exceptional, (82)
"The place was clean and nice, no problems at all. Plenty of room for my family. Wish we could have stayed longer!"
United States
Brad W.
$356 nightly
The price is $396
Dec 11 - Dec 12
Total with taxes and fees
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina
On the beach, sun loungers, beach towels
NEW ! Marvelous 2-bedroom house with Marina in Key Largo

NEW ! Marvelous 2-bedroom house with Marina in Key Largo

NEW ! Marvelous 2-bedroom house with Marina in Key Largo
2.0 star property
Key Largo
10.0 out of 10, Exceptional, (44)
"Good location. Lagoon and pool right outside door. "
United States
Debra C.
$464 nightly
The price is $515
Dec 11 - Dec 12
Total with taxes and fees
NEW ! Marvelous 2-bedroom house with Marina in Key Largo
Interior
4. Cozy Waterfront Apartment in Key Largo!

4. Cozy Waterfront Apartment in Key Largo!

4. Cozy Waterfront Apartment in Key Largo!
Key Largo
9.8 out of 10, Exceptional, (11)
"We loved our stay at the waterfront cabanas! The location is 10/10 with an awesome waterfront bar/restaurant and coffee truck within walking distance. We truly felt like keys locals staying here - highly recommend! "
United States
Brittany M.
4. Cozy Waterfront Apartment in Key Largo!
Beach
Casa Largo

Casa Largo

Casa Largo
Key Largo
9.0 out of 10, Wonderful, (129)
"We stayed in 2 vrbo properties while in Florida. This one met and exceeded our expectations. We would stay again without hesitation."
United States
Kelly M.
$482 nightly
The price is $535
Dec 11 - Dec 12
Total with taxes and fees
Casa Largo
Property grounds
Keys Relaxing Getaway

Keys Relaxing Getaway

Keys Relaxing Getaway
Key Largo
10.0 out of 10, Exceptional, (57)
"All new and very clean. Great place to stay."
United States
M D.
$512 nightly
The price is $568
Dec 11 - Dec 12
Total with taxes and fees
Keys Relaxing Getaway
On the beach, sun loungers, beach towels
NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS

NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
Key Largo
9.8 out of 10, Exceptional, (194)
"Martha was great! Property is centrally located. Beds were comfortable. Jetty is convenient for fishing. Beware of mosquitos at dark! Would definitely do again!"
United States
Michael H.
NEW! CASA AZUL OCEANSIDE - GOLF CART, 2 KING SUITES, POOL, BEACH, PICKLE, KAYAKS
A heated pool
Lovely Bungalow w/ Plenty Of Shade at Largo Resort

Lovely Bungalow w/ Plenty Of Shade at Largo Resort

Lovely Bungalow w/ Plenty Of Shade at Largo Resort
Key Largo
10.0 out of 10, Exceptional, (17)
"Our bungalow was very clean and the beds were very comfortable! It was almost like we we're on our own private island and my 8 year old loved it! We hope to come back on our next visit!"
United States
Elizabeth M.
$382 nightly
The price is $421
Dec 15 - Dec 16
Total with taxes and fees
Lovely Bungalow w/ Plenty Of Shade at Largo Resort
A heated pool
Beautiful Oceanside Mariner`s 3 Bedroom Townhome

Beautiful Oceanside Mariner`s 3 Bedroom Townhome

Beautiful Oceanside Mariner`s 3 Bedroom Townhome
Rock Harbor
10.0 out of 10, Exceptional, (86)
"Great place, great hosts. We'll probably be backThank you"
United States
Curt B.
$490 nightly
The price is $543
Dec 11 - Dec 12
Total with taxes and fees
Beautiful Oceanside Mariner`s 3 Bedroom Townhome
A heated pool
Marina Villa 212 3/3 Pools, Marina and Ocean views

Marina Villa 212 3/3 Pools, Marina and Ocean views

Marina Villa 212 3/3 Pools, Marina and Ocean views
Rock Harbor
10.0 out of 10, Exceptional, (130)
"The Villa was beautiful and had everything we needed for the weekend!"
United States
Elizabeth K.
$835 nightly
The price is $926
Dec 24 - Dec 25
Total with taxes and fees
Marina Villa 212 3/3 Pools, Marina and Ocean views
Indoor pool, outdoor pool
Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!

Ohana Cay 2brm/2bth - Book your getaway!
Rock Harbor
10.0 out of 10, Exceptional, (92)
"Perfect location and great community. Easy docking at the marina and nice amenities. "
United States
Gene Z.
$725 nightly
The price is $806
Jan 3 - Jan 4, 2026
Total with taxes and fees
Ohana Cay 2brm/2bth - Book your getaway!
Outdoor dining
Oceanside Kawama Villa R5

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (180)
"Very very nice villa in a superb location… Abcolutely loved the property!"
United States
Ricardo G.
Oceanside Kawama Villa R5
An infinity pool, a heated pool
Tranquil Bungalow at the Beautiful at Largo Resort

Tranquil Bungalow at the Beautiful at Largo Resort

Tranquil Bungalow at the Beautiful at Largo Resort
Key Largo
9.6 out of 10, Exceptional, (7)
"10/10! This property itself is secluded and very safe. The pool and views were breathtaking. The complimentary paddle boards and bicycles were fun and just an extra service that bettered our experience. The employees were amazing, kind, and professional. The bungalow was so comfortable and smelt amazing when we entered. Beds were comfortable and the little kitchen was used! Plates, silverwear, & cups were provided thankfully. The host!!!! 100/10. Thank you!!!! She was able to provide a nice...
United States
Nancy H.
$427 nightly
The price is $471
Dec 15 - Dec 16
Total with taxes and fees
Tranquil Bungalow at the Beautiful at Largo Resort
Outdoor dining
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
Key Largo
9.6 out of 10, Exceptional, (123)
"Great stay!! Location was perfect view of the canal and close to the pool. Unit was very clean and would definitely stay again!!"
United States
Brad T.
$393 nightly
The price is $436
Dec 14 - Dec 15
Total with taxes and fees
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
On the beach
Key largo Kawama Villa N2

Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
9.6 out of 10, Exceptional, (133)
"Great villa!"
United States
Georgi T.
Key largo Kawama Villa N2
Marina
Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Tiny House w Pool, Beach, and Boat Dock

Waterfront Tiny House w Pool, Beach, and Boat Dock
Key Largo
9.6 out of 10, Exceptional, (62)
"Great little place with awesome outdoor area. "
United States
James D.
$365 nightly
The price is $405
Dec 11 - Dec 12
Total with taxes and fees
Waterfront Tiny House w Pool, Beach, and Boat Dock
Pool
Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo
10.0 out of 10, Exceptional, (4)
"Loved the location and views, house is amazing"
United States
Dan L.
$713 nightly
The price is $795
Dec 14 - Dec 15
Total with taxes and fees
Key Largo Oasis Oceanfront with Pool & Hot Tub
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

Fisher Inn Resort & Marina

Fisher Inn Resort & Marina

10/10 Excellent
"Clean fresh rooms, facilities and property! Extraordinary customer service. Great kayaks and paddleboards to use free. I would definitely stay here again"
Kristi 2-night trip
Posted 17 hours ago
Fisher Inn Resort & Marina

Find out more about Windley Key

Windley Key Vacation Homes information

Number of reviews
1,367
Accommodation
630 Vacation Homes
Lowest Price
$339
Highest Price
$926

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