A colorful building with a sign reading "Florida Keys Brewing Co." and a Santa Claus decoration.

Search Vacation Homes in Windley Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Windley Key holiday homes

On the beach

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, (49 reviews)
"We had a great time. Loved the kayaks!!"
United States
Laurie S.
The price is HK$949
HK$2,900 total
includes taxes & fees
12 Jul - 13 Jul
Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Terrace/patio

Las Olas

Las Olas
Cross Key Waterways
The price is HK$7,056
HK$11,428 total
includes taxes & fees
10 Jul - 11 Jul
Las Olas
Smart TV

Charming Home in Key Largo

Charming Home in Key Largo
Key Largo
9.8 out of 10, Exceptional, (38 reviews)
"Very clean and nice location."
United States
Melinda V.
The price is HK$1,172
HK$3,275 total
includes taxes & fees
13 Jul - 14 Jul
Charming Home in Key Largo
2 bedrooms, iron/ironing board, WiFi, bed sheets

Little Peace of Haven

Little Peace of Haven
Key Largo
10.0 out of 10, Exceptional, (1 review)
"Great place to stay."
United States
Jacob S.
The price is HK$1,270
HK$3,385 total
includes taxes & fees
17 Jul - 18 Jul
Little Peace of Haven
Fridge, microwave, stovetop, coffee/tea maker

Beautiful bungalow with AC and Hot tub in Tavernier

Beautiful bungalow with AC and Hot tub in Tavernier
florida
The price is HK$1,475
HK$2,714 total
includes taxes & fees
13 Jul - 14 Jul
Beautiful bungalow with AC and Hot tub in Tavernier
Dining

Sunrise Escape - Ocean Front Villa - Sleeps 10

Sunrise Escape - Ocean Front Villa - Sleeps 10
Key Largo
9.8 out of 10, Exceptional, (71 reviews)
"Host was very responsive, location safe and wuiet."
United States
Tracey C.
The price is HK$2,337
HK$6,367 total
includes taxes & fees
9 Aug - 10 Aug
Sunrise Escape - Ocean Front Villa - Sleeps 10
Beach

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes

Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Key Largo
9.6 out of 10, Exceptional, (137 reviews)
"Had fun villa was in good condition."
United States
Michelle S.
The price is HK$2,906
HK$5,545 total
includes taxes & fees
3 Aug - 4 Aug
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Property grounds

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.

NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Key Largo
10.0 out of 10, Exceptional, (60 reviews)
"Great amenities. Immaculate apartment. Kids loved the lagoon. Super responsive host. Note - beds are memory foam. "
United States
Joshua K.
The price is HK$2,258
HK$4,798 total
includes taxes & fees
21 Jul - 22 Jul
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
Dining

Keys Cottage with Beach and Dockage! Bayfront Property!

Keys Cottage with Beach and Dockage! Bayfront Property!
Key Largo
9.4 out of 10, Exceptional, (36 reviews)
"We had such a wonderful time here! The house was perfect and the grounds were beautiful! We will definitely come again! "
United States
Julia W.
Keys Cottage with Beach and Dockage! Bayfront Property!
Smart TV

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

New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
Key Largo
8.0 out of 10, Very good, (1 review)
"Tiny HomeThis tiny home was comfortable, clean, and fully stocked with all you need to vacation in the Keys! At first, I was hesitant on booking a tiny home coming from a 3,200sqft house but we found the layout functional and actually cozy with good amounts of space.I would recommend the place along with the property management team who ensured all communications were answered quickly and thoroughly!Would stay here again!"
United States
Christina R.
The price is HK$996
HK$2,976 total
includes taxes & fees
13 Jul - 14 Jul
New Tiny Home-Paddle Boards, Kayaks, Pool, Marina
Beach nearby, sun-loungers, beach towels

FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Key Largo
9.4 out of 10, Exceptional, (67 reviews)
"The pool was clean and enjoying "
United States
Aaron G.
The price is HK$2,940
HK$6,147 total
includes taxes & fees
21 Jul - 22 Jul
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Beach nearby

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Key Largo
The price is HK$1,003
HK$2,907 total
includes taxes & fees
12 Jul - 13 Jul
Beachfront Retreat w Pool, Boat Ramp & Dock Rental
Marina

Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car

Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car
Key Largo
10.0 out of 10, Exceptional, (147 reviews)
The price is HK$2,744
HK$6,146 total
includes taxes & fees
13 Jul - 14 Jul
Waterfront Home 3/2.5,HotTub,2Sup,4Kayaks,Golf Car
Beach nearby

Key largo Kawama Villa N2

Key largo Kawama Villa N2
Key Largo
9.6 out of 10, Exceptional, (134 reviews)
"The condo was perfectly appointed with everything we would want or need, including some snorkel masks, beach towels, bikes. Really a wonderful stay. Thanks."
United States
Wendy R.
The price is HK$2,898
HK$5,559 total
includes taxes & fees
12 Jul - 13 Jul
Key largo Kawama Villa N2
A heated pool

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more

Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Rock Harbor
10.0 out of 10, Exceptional, (14 reviews)
"Place was perfect in many ways!!!!"
United States
Brandon M.
The price is HK$2,752
HK$7,403 total
includes taxes & fees
15 Jul - 16 Jul
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Smart TV, stereo

Waterfront Tiny Home Pool Dock Kayaks Paddleboards

Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Key Largo
9.6 out of 10, Exceptional, (129 reviews)
"I cannot say enough about our stay at the Key Largo Campground. The amenities, and atmosphere exceeded our expectations. Our stay was hands down, the perfect place to spend our very first Valentine's Day together.The unit was super cozy and private. My wife and I will certainly be back!!!"
United States
Jason C.
The price is HK$1,663
HK$3,821 total
includes taxes & fees
13 Jul - 14 Jul
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Beach nearby

Key Largo Villa, Kawama K5, 3/3

Key Largo Villa, Kawama K5, 3/3
Key Largo
10.0 out of 10, Exceptional, (66 reviews)
"Lovely location and nice kitchen."
United States
Susan S.
The price is HK$2,665
HK$5,366 total
includes taxes & fees
16 Jul - 17 Jul
Key Largo Villa, Kawama K5, 3/3
Interior

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

New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Key Largo
9.2 out of 10, Wonderful, (21 reviews)
"Great location "
United States
jenny p.
The price is HK$2,564
HK$4,581 total
includes taxes & fees
9 Aug - 10 Aug
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
Outdoor dining

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (183 reviews)
"Great place in Key Largo. Cool bonus a saltwater lagoon with fish to swim and snorkwl with. "
United States
Kenny C.
The price is HK$3,062
HK$5,766 total
includes taxes & fees
12 Jul - 13 Jul
Oceanside Kawama Villa R5
Property grounds

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, (66 reviews)
The price is HK$1,466
HK$3,521 total
includes taxes & fees
3 Aug - 4 Aug
Waterfront Tiny House w Pool, Beach, and Boat Dock
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windley Key Hotel Reviews

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"For the price, it was great! We did get the smaller room which was much smaller than I thought. However, it was perfect for my husband and I who really only needed the room for getting ready and sleeping. The room was very clean, and we loved the little porch we had connected to our room. The property was beautiful with its tropical trees and beach. However, unless you get there first, space on the beach and chairs on the dock are limited. But the property is located close to many great restaurants and coffee shops as well as many places to snorkel. Over all, great stay!"
Nicole 5-night trip
Posted 1 hour ago
The Pelican Key Largo Cottages

Find out more about Windley Key

Windley Key Vacation Homes information

Number of reviews
1,199
Accommodation
602 Vacation Homes
Lowest Price
HK$2,714
Highest Price
HK$7,403

Explore a world of travel with Expedia