Search Windley Key Villa Rentals from CA $642

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Browse Select Windley Key Villas

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (54)
"Lovely room with friendly staff. "
The price is CA $828
CA $1,010 total
includes taxes & fees
Apr 6 - Apr 7
The Islands of Islamorada

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

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

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

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

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

9.6 out of 10, Exceptional, (63)
"My husband and I traveled to Key Largo with friends and absolutely enjoyed our condo and the amenities the HOA has to offer!"
The price is CA $642
CA $1,277 total
includes taxes & fees
Apr 17 - Apr 18
SPACIOUS 3/3.5 VILLA - INDOOR PICKLEBALL - MOST UPSCALE OCEANFRONT RESORT IN KL!

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

10.0 out of 10, Exceptional, (109)
"The property and the location was absolutely perfect. "
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

Twilight with Resort Privileges

Twilight with Resort Privileges

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

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!

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

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

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

10.0 out of 10, Exceptional, (1)
"Fantastic location with loads of bars and restaurants within walking distance. Property is lovely, very clean and modern with a great pool. Definitely stay again."
Isla Kiwi: Waterfront Boutique Resort, Htd Pool, Dock, Walkable

Tranquility with Resort Privileges

9.8 out of 10, Exceptional, (7)
"The property, house and amenities at the resort couldn’t have been nicer."
Tranquility with Resort Privileges

Hideaway with Resort Privileges

9.6 out of 10, Exceptional, (17)
"The resort access was an added bonus and made our stay really memorable."
Hideaway with Resort Privileges

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

10.0 out of 10, Exceptional, (1)
"This was a beautiful spot for 3 couples to relax and enjoy this beautiful setting. The outside space was perfect with tables, firepit & grills. The house was stocked well enough to be able to prepare some meals. I would definitely return again."
Bayberry Key: Waterfront Htd Pool, Dock, Walkable, Direct Water views!

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 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!

Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

9.8 out of 10, Exceptional, (48)
"Kawama Community Resort is ideal for families large and small. Resort offers multiple pools, is ocean side and is a safe gated community. Walking distance to marinas, fisheries. Less than 1 mile to a local Publix grocery store and multiple eateries. Right off of route 1. Kids can easily entertain selves by fishing, swimming and snorkeling in the lagoon, pickelball and pools. A few Community firepits and grills to use. Our group was a party of 40 for spring break and the accommodations fit all of...
Oceanfront Villa overlooking the Atlantic and Molasses Reef Marina

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

10.0 out of 10, Exceptional, (175)
"We just spent a week at Windley Cottage and had an amazing time. The house was very clean and comfortable for our family of 4. Everything was comfortable and we felt very safe and at ease in the community. The property was centrally located to what the keys have to offer. Communicating with Roger and Linda was so easy and they were more than helpful with questions we had. I would stay here again in a heart beat and recommend it to anyone."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (435)
"Cool, big pool area! Friendly staff"
The price is CA $199
CA $298 total
includes taxes & fees
Apr 6 - Apr 7
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (54)
"Lovely room with friendly staff. "
The price is CA $828
CA $1,010 total
includes taxes & fees
Apr 6 - Apr 7
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.