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

Holiday Homes in Windley Key

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Windley Key holiday homes

2 bedrooms, iron/ironing board, WiFi, bed sheets

Little Peace of Haven

Little Peace of Haven
Key Largo
10.0 out of 10, Exceptional, (3 reviews)
"Lovely clean, quiet, perfect location for exploring the upper keys! An fantastic value!"
United States
Mitchel R.
The price is AU$607
includes taxes & fees
31 July - 1 Aug
Little Peace of Haven
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 AU$553
includes taxes & fees
11 Aug - 12 Aug
Charming Home in Key Largo
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 AU$1,058
includes taxes & fees
18 Aug - 19 Aug
Sunrise Escape - Ocean Front Villa - Sleeps 10
On the beach, sun-loungers, beach towels

NEW! Casa Palma - NO HIDDEN FEES! Golf Cart, 2 King, Pool, Beach, Tennis, Kayaks

NEW! Casa Palma - NO HIDDEN FEES! Golf Cart, 2 King, Pool, Beach, Tennis, Kayaks
Key Largo
9.8 out of 10, Exceptional, (177 reviews)
"Our host Martha is a star; very responsive and helpful. We had a great time."
United States
Doug D.
The price is AU$1,397
includes taxes & fees
1 Aug - 2 Aug
NEW! Casa Palma - NO HIDDEN FEES! Golf Cart, 2 King, Pool, Beach, Tennis, Kayaks
Beach

Key Largo Kawama Villa L1, 3/3

Key Largo Kawama Villa L1, 3/3
Key Largo
9.4 out of 10, Exceptional, (226 reviews)
"Nice place and convenient location."
United States
Barbara W.
Key Largo Kawama Villa L1, 3/3
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, (140 reviews)
"Had fun villa was in good condition."
United States
Michelle S.
The price is AU$843
includes taxes & fees
20 Aug - 21 Aug
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
Outdoor dining

Oceanside Kawama Villa R5

Oceanside Kawama Villa R5
Key Largo
9.2 out of 10, Wonderful, (184 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 AU$956
includes taxes & fees
9 Aug - 10 Aug
Oceanside Kawama Villa R5
Beach nearby

Key Largo Villa, Kawama P6, 3/3

Key Largo Villa, Kawama P6, 3/3
Key Largo
9.8 out of 10, Exceptional, (148 reviews)
"Beautiful, clean home. Loved the property and the inlet with all the fish was amazing. Would stay again."
United States
Sandra C.
The price is AU$972
includes taxes & fees
13 Aug - 14 Aug
Key Largo Villa, Kawama P6, 3/3
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, (61 reviews)
"The place was amazing just a shame we couldn't stay longer. Definitely going to be rebooking in the future "
United States
Nelson S.
The price is AU$879
includes taxes & fees
10 Aug - 11 Aug
NEW ! Lagoon-front townhouse with Marina! Day Dreams Key Largo.
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.
Key Largo Villa, Kawama K5, 3/3
TV, video games

Key Largo Oasis Oceanfront with Pool & Hot Tub

Key Largo Oasis Oceanfront with Pool & Hot Tub
Key Largo
9.6 out of 10, Exceptional, (5 reviews)
"Unit was beautiful with great view Love that it had an elevator made it easy to load in luggage and everything else"
United States
Denise A.
The price is AU$1,388
includes taxes & fees
23 Aug - 24 Aug
Key Largo Oasis Oceanfront with Pool & Hot Tub
Coffee/tea maker, fridge, microwave, stovetop

Beautiful bungalow with AC and Hot tub in Tavernier

Beautiful bungalow with AC and Hot tub in Tavernier
florida
The price is AU$475
includes taxes & fees
10 Aug - 11 Aug
Beautiful bungalow with AC and Hot tub in Tavernier
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, (16 reviews)
"Place was perfect in many ways!!!!"
United States
Brandon M.
The price is AU$1,360
includes taxes & fees
18 Aug - 19 Aug
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Marina

Cozy Waterfront Apartment in Key Largo!

Cozy Waterfront Apartment in Key Largo!
Key Largo
9.8 out of 10, Exceptional, (12 reviews)
"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.
The price is AU$480
includes taxes & fees
31 July - 1 Aug
Cozy Waterfront Apartment in Key Largo!
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
9.0 out of 10, Wonderful, (22 reviews)
"The lagoon was beautiful and fun."
United States
Teresa H.
The price is AU$704
includes taxes & fees
3 Aug - 4 Aug
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
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.
The price is AU$844
includes taxes & fees
10 Aug - 11 Aug
Keys Cottage with Beach and Dockage! Bayfront Property!
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 AU$536
includes taxes & fees
12 Aug - 13 Aug
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Microwave, oven, stovetop, dishwasher

Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is AU$1,467
includes taxes & fees
12 Aug - 13 Aug
Oceanside Retreat w/Rooftop, Pool & Kayaks
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

The Pelican Key Largo Cottages

The Pelican Key Largo Cottages

10/10 Excellent
"Super fun, everything was perfect and staff were great!"
Elijah 2-night trip
Posted less than an hour ago
The Pelican Key Largo Cottages

Find out more about Windley Key

Windley Key Holiday Homes information

Number of reviews
1,334
Accommodation
604 Holiday Homes
Lowest Price
AU$475
Highest Price
AU$1,467

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