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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Featured Villas in Windley Key and around

The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Lovely room with friendly staff. "
The price is €647
includes taxes & fees
6 Apr - 7 Apr
The Islands of Islamorada
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
On the beach, sun-loungers, beach towels

Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

10.0 out of 10, Exceptional, (108)
"Lovely condo and property "
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
Endless Summer with Resort Privileges
On the beach

Endless Summer with Resort Privileges

9.4 out of 10, Exceptional, (12)
"We had a lovely weekend staying on the property. It was spacious and convenient a very nice facility and access to the resort made it outstanding. It was very easy to order groceries for delivery, which were there waiting for us when we arrived. I definitely recommend this property for anyone with a larger group or family. I do suggest that the management let guests know the number of the unit they are renting just to facility logistics like ordering groceries. However, I was easily able to find...
Endless Summer with Resort Privileges
Sandcastle Luxury Villa in Key Largo with Resort Privileges
Beach

Sandcastle Luxury Villa in Key Largo with Resort Privileges

10.0 out of 10, Exceptional, (2)
"The house was gorgeous and we would definitely recommend it to everyone."
Sandcastle Luxury Villa in Key Largo with Resort Privileges
Gull's Nest with Resort Privileges
Beach

Gull's Nest with Resort Privileges

9.4 out of 10, Exceptional, (20)
"Not far from miami airport. Great resort access. Beautiful and clean lodging. Food is also great as resort. Will rebook! "
Gull's Nest with Resort Privileges
Newly upgraded Key Largo Villa W/Boat Slip
A heated pool

Newly upgraded Key Largo Villa W/Boat Slip

10.0 out of 10, Exceptional, (78)
"Great location and beautifully decorated home. Perfect boat parking and set up for a fishing family. Annie was super responsive and a great host. We can’t wait to book again!"
Newly upgraded Key Largo Villa W/Boat Slip
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Property grounds

LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!

9.4 out of 10, Exceptional, (57)
"Awesome time perfect for mature adults. This place was great to relax and unwind. Average age @ 65. Which is right near our range"
The price is €676
includes taxes & fees
21 Mar - 22 Mar
LICENSED MANAGER - MODERN 2/2 COCONUT PALM VILLA - OCEANFRONT BEACH RESORT!
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
Marina

Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

9.8 out of 10, Exceptional, (47)
"Had a wonderful stay. Easy access to many area activities."
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina
Sea Haven with Resort Privileges
Beach

Sea Haven with Resort Privileges

10.0 out of 10, Exceptional, (2)
"Place was clean. Shuttle from house to resort was quick & reliable. Resort very nice."
Sea Haven with Resort Privileges
Isla Honeydew: 3 En-Suite Bedrooms! Waterfront Resort, Pool, Dock!
A heated pool

Isla Honeydew: 3 En-Suite Bedrooms! Waterfront Resort, Pool, Dock!

3.0 star property
10.0 out of 10, Exceptional, (3)
"The home was just as it was described on the website! Beautiful, comfortable and clean. Plenty of cooking items. Location was wonderful-we could walk to several restaurants and store. Would stay again!"
Isla Honeydew: 3 En-Suite Bedrooms! Waterfront Resort, Pool, Dock!
Isla Guava: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Pool

Isla Guava: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

10.0 out of 10, Exceptional, (1)
"We’ve vacationed in the Keys many times and this property was the best. First is location. It’s on a canal cut off Little Basin. There are many walkable restaurants and attractions. The house itself was very clean and the layout conducive to renters with two master suites upstairs and a smaller bedroom and bath down. Property management very attentive and communicative with a very nice young lady coming on site. Beautiful pool area and deck by water. Can’t go wrong with this."
Isla Guava: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!
Outdoor pool, a heated pool

MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!

9.6 out of 10, Exceptional, (40)
"Took a group of guys to go down for relaxation and fishing. Resort was perfect for relaxing. Condo itself was excellent and the heated pool and grotto were well used. If you choose to fish there is ample opportunity with local charters and the one day it rained we visited several local breweries. Perfect getaway."
MODERN VILLA - INDOOR PICKLEBALL - KL'S MOST UPSCALE OCEANFRONT RESORT & MARINA!
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
Pool

Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay

10.0 out of 10, Exceptional, (89)
"This is a great spot to get to so many fun things to do in the keys. Whether you are driving, walking, or going by boat. It's a wonderful community with friendly people staying around you and a perfect spot for sunsets!"
Keys Kottage; Remodeled Villa in Native Hammock on Florida Bay
Latitudes with Resort Privileges
Beach

Latitudes with Resort Privileges

8.0 out of 10, Very good, (2)
"The house was nice, reasonably located. Our checkin was seamless and required only an email. The house was nice, clean, brand new and had reasonable furnishings. The house itself lacked many standard and or listed items such as a grill, adequate table ware, bedding, functional ice-maker, toaster, coat hangers, hair dryer, iron/ironing board… and trying to get the property manager to respond took 48 hours+. The walk to the resort is .6 miles but requires navigation across a four lane highway...
Latitudes with Resort Privileges
Waterfront House with Boat Dock
Terrace/patio

Waterfront House with Boat Dock

5.0 star property
6.0 out of 10, (1)
"Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration."
Waterfront House with Boat Dock
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!
Outdoor pool, a heated pool

SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

9.6 out of 10, Exceptional, (62)
"My husband and I traveled to Key Largo with friends and absolutely enjoyed our condo and the amenities the HOA has to offer!"
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!
Outdoor pool, a heated pool

SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!

9.4 out of 10, Exceptional, (26)
"We visited with 9 adults and had a great week at the condo and pools. Having 2 stories worked out perfect for us. Our kids and their friends had a separate area to hang out. The place was clean and exactly as described, and the hosts provided clear instructions for arrival and departure. We had no issues all week and loved using the pools, hot tubs, exercise facility, and games room. Shopping was convenient, and we took a trip snorkeling as well. Everything you’d want was near-by."
SPACIOUS 4/3.5 VILLA! INDOOR PICKLEBALL! MOST UPSCALE OCEANFRONT RESORT IN KL!
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Exterior

Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl

Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!
A heated pool

Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

10.0 out of 10, Exceptional, (1)
Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
Pool

Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

10.0 out of 10, Exceptional, (3)
"This place is a gem!!"
Isla Mamey: Waterfront Boutique Resort, Htd Pool, Dock, Walkable
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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Other property types in Windley Key

OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
A heated pool

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

10.0 out of 10, Exceptional, (174)
"We've visited Angler's Reef many times over the years and haven't been let down yet. First time in Linda's & Roger's home. It is a very nice home; furnishings nice, appliances all work, home was just as described. Owners were easy to communicate with; converted twins to King and arranged dock access for us in advance. I'd highly recommend to anyone. "
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards
Breezy Palms Resort
Exterior

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (422)
"We visited Breezy Palms for our 20th wedding anniversary. We took advantage of the boat rental on site, had a great day on the water. Played cards on our lanai. Used the lovely pool, walked to local restaurants, and had a memorable time. Definitely will be back!"
The price is €209
includes taxes & fees
6 Apr - 7 Apr
Breezy Palms Resort
The Islands of Islamorada
2 outdoor pools, open 8:00 AM to 6:00 PM, pool loungers

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Lovely room with friendly staff. "
The price is €647
includes taxes & fees
6 Apr - 7 Apr
The Islands of Islamorada
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.