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
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Windley Key vacation 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, (1 review)
"Great place to stay."
United States
Jacob S.
The price is AED 595
AED 1,593 total
includes taxes & fees
25 Jul - 26 Jul
Little Peace of Haven
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 AED 1,489
AED 2,794 total
includes taxes & fees
9 Aug - 10 Aug
Oceanside Kawama Villa R5
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 AED 533
AED 1,508 total
includes taxes & fees
11 Aug - 12 Aug
Charming Home in Key Largo
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 AED 1,309
AED 2,825 total
includes taxes & fees
21 Jul - 22 Jul
FULL TIME LIC MGR - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
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, (138 reviews)
"Had fun villa was in good condition."
United States
Michelle S.
The price is AED 964
AED 2,058 total
includes taxes & fees
20 Aug - 21 Aug
Key Largo Villa, Kawama J3, 3/3, Ocean,Marina,Lagoon,Pools,Kayaks&bikes
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)
"We enjoyed our stay! House was spotless. Easy and quick communication. We enjoyed the resort amenities."
United States
Elizabeth M.
The price is AED 1,183
AED 2,447 total
includes taxes & fees
23 Jul - 24 Jul
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)
"Great amenities. Immaculate apartment. Kids loved the lagoon. Super responsive host. Note - beds are memory foam. "
United States
Joshua K.
The price is AED 1,058
AED 2,252 total
includes taxes & fees
21 Jul - 22 Jul
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.
The price is AED 1,337
AED 2,617 total
includes taxes & fees
21 Jul - 22 Jul
Key Largo Villa, Kawama K5, 3/3
Coffee/tea maker, fridge, microwave, oven

New Oceanside Paradise with Pool and Waterfront Views!

New Oceanside Paradise with Pool and Waterfront Views!
Key Largo
10.0 out of 10, Exceptional, (2 reviews)
"Everything was great "
United States
Ravone L.
The price is AED 1,427
AED 3,148 total
includes taxes & fees
21 Jul - 22 Jul
New Oceanside Paradise with Pool and Waterfront Views!
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 AED 898
AED 2,735 total
includes taxes & fees
17 Aug - 18 Aug
Sunrise Escape - Ocean Front Villa - Sleeps 10
Microwave, oven, stovetop, dishwasher

Oceanside Retreat w/Rooftop, Pool & Kayaks

Oceanside Retreat w/Rooftop, Pool & Kayaks
Key Largo
The price is AED 1,901
AED 3,691 total
includes taxes & fees
21 Jul - 22 Jul
Oceanside Retreat w/Rooftop, Pool & Kayaks
Outdoor pool, a heated pool

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES

NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
Rock Harbor
9.8 out of 10, Exceptional, (115 reviews)
"Nicely decorated and nice location. "
United States
Rob L.
The price is AED 3,207
AED 5,785 total
includes taxes & fees
1 Aug - 2 Aug
NEW! OCEANFRONT SHOWHOUSE CASA MAR • NO RESORT OR MANAGMENT FEES • 2 KING SUITES
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, (15 reviews)
"Place was perfect in many ways!!!!"
United States
Brandon M.
The price is AED 1,325
AED 3,464 total
includes taxes & fees
19 Aug - 20 Aug
Sunrise Retreat: Ocean & Pool Views, Gym, PB Courts, Game Room, Marina and more
Terrace/patio

The Coral House - Bayside Retreat for 6-8 guests

The Coral House - Bayside Retreat for 6-8 guests
Key Largo
7.0 out of 10, Good, (9 reviews)
"Great location with private beach loved it "
United States
Bobby A.
The price is AED 3,673
AED 4,195 total
includes taxes & fees
21 Jul - 22 Jul
The Coral House - Bayside Retreat for 6-8 guests
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 AED 1,043
AED 1,976 total
includes taxes & fees
21 Jul - 22 Jul
New! Lagoon-front 2-BR townhome, Key Largo, gated waterfront community, 2 pools
1 bedroom, bed sheets

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.

Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
Key Largo Village
10.0 out of 10, Exceptional, (1 review)
"This is by far the BEST experience I’ve ever had. Upon arrival, we were greeted by the boat driver, Captain Ryan. The ride over was easy and quick. We rode with 1 other couple and the captain helped everyone aboard, with a hand and carried our luggage aboard. He had a very friendly demeanor. He had knowledge of the wildlife in the area and told us to keep an eye out for manatee and dolphins, which we saw within a 1/2 hour of being dropped off. He brought dinner to us, which was still hot and he...
United States
Stacey P.
The price is AED 3,352
AED 4,030 total
includes taxes & fees
21 Jul - 22 Jul
Premium Floating Bugalow by Stay Ombi in the Keys with Stunning Ocean Views.
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 AED 707
AED 1,279 total
includes taxes & fees
28 Jul - 29 Jul
Beautiful bungalow with AC and Hot tub in Tavernier
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 AED 613
AED 1,582 total
includes taxes & fees
21 Jul - 22 Jul
Waterfront Tiny Home Pool Dock Kayaks Paddleboards
Outdoor pool, a heated pool

FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!

FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
Rock Harbor
9.4 out of 10, Exceptional, (40 reviews)
"Great location, lots to do in the resort. "
United States
Erica H.
The price is AED 2,006
AED 4,155 total
includes taxes & fees
27 Jul - 28 Jul
FULL TIME LIC MGR - INDOOR/OUTDOOR PICKLEBALL - SPEAKEASY - OCEANFRONT RESORT!
Outdoor dining

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi

Bay Sunsets Free Kayaks/Paddleboard Jacuzzi
Key Largo
10.0 out of 10, Exceptional, (86 reviews)
"Great place to stay in a great location "
United States
Will H.
The price is AED 3,287
AED 5,794 total
includes taxes & fees
26 Jul - 27 Jul
Bay Sunsets Free Kayaks/Paddleboard Jacuzzi
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

Lime Tree Bay Resort

Lime Tree Bay Resort

10/10 Excellent
"Great property with beach access, and amazing snorkeling right off the beach! Well maintained property and spotless rooms! Staff very helpful!"
Marie 3-night trip
Posted 10 hours ago
Lime Tree Bay Resort