Windley Key Vacation Rentals

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Vacation Rentals in Windley Key

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

10.0 out of 10, Exceptional, (172)
"The house we stayed in was immaculate and so attractive-exactly as pictured. We felt very safe in the gated community. We used the kayaks and pool and walked the area frequently. We rented bikes and had great areas to ride in. This was a very quiet, relaxing vacation. Lots of waterside restaurants to enjoy. The owner, Roger, was a great communicator."
OCEANFRONT ANGLERS REEF ISLAMORADA HOME- Pool, Dock, Beach, Kayaks,Paddle Boards

Breezy Palms Resort

2.5 star property
8.6 out of 10, Excellent, (413)
"Wonderful experience - highly recommend!! From check in to check out was great. All staff were very helpful, property was well kept, relaxing, quiet & very easy location to site’s & restaurants. "
The price is ¥26,512
¥37,577 total
includes taxes & fees
Mar 25 - Mar 26
Breezy Palms Resort

The Islands of Islamorada

4.0 star property
9.8 out of 10, Exceptional, (52)
"Everything was lovely except I felt rushed on my departure date. A front desk representative knocked around 9am to find out what time I was leaving. If your check out policy is 11am, you should not knock on people’s door to find out what time they are planning on leaving. It doesn’t feel like a luxurious experience when you do. In addition to the early knock, the entire housekeeping staff was waiting by my front door when I checked out at 10:25. What if I wasn’t checking out at 10:25 and was...
The price is ¥120,759
¥144,082 total
includes taxes & fees
Feb 25 - Feb 26
The Islands of Islamorada

Key Largo Cottages

2.5 star property
9.4 out of 10, Exceptional, (20)
"Love this place! Very friendly and secluded. Not your typical resort-look elsewhere if that’s what you want. But if you want a friendly private sailing camp where you hang out with other fun people and like to sail and kayak, this is absolutely it! The use of the sailboat alone more than pays for the room."
The price is ¥48,766
¥77,159 total
includes taxes & fees
Feb 25 - Feb 26
Key Largo Cottages

Beachfront Retreat w Pool, Boat Ramp & Dock Rental

9.0 out of 10, Wonderful, (28)
"Nice facilities. Wish we had better weather. Always enjoy our home away from home. KEYS LIFE FOR ME!!!!"
The price is ¥26,277
¥60,479 total
includes taxes & fees
Feb 24 - Feb 25
Beachfront Retreat w Pool, Boat Ramp & Dock Rental

Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

9.8 out of 10, Exceptional, (46)
"We stayed a week in the wonderful resort at Kawama. The lagoon was right in front of our unit. There were beautiful tropical fish in the lagoon as well as tarpons and lobster! The 2 pools were heated and delightful to swim in. We love walking out to the end of the jetty each evening to watch the sunset. It was a fantastic place to spend a week and soak up the sun."
Waterfront - Private Lagoon - in Park on the Ocean side -beach, pool

Island Bay Resort

2.5 star property
10.0 out of 10, Exceptional, (101)
"Great place to turn off the iPhone and relax. Bring your snacks, build a charcuterie board or two and pop a cork. Wonderful calm area to kayak or paddle board even if you’re not a pro. Nice bay cove with iguanas! Sue and Steve’s hospitality is exceptional. "
Island Bay Resort

Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

9.8 out of 10, Exceptional, (10)
"Really nice place, no surprises. Location was excellent and pictures and description very accurate. Unfortunately, the weather was not in our favor but can't control that! Would definitely stay here again."
The price is ¥43,364
¥76,747 total
includes taxes & fees
Mar 6 - Mar 7
Cozy Waterfront Retreat w/ Private Boat Dock + Tiki

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

9.4 out of 10, Exceptional, (50)
"Loved the Tiny Home! Perfect for our family of five, 3 of which are teenagers. Great community, amenities, and friendly folks. Key Largo is such a fun place to vacation! Host was very communicative and friendly, would stay here again! Thanks for a fun trip!"
The price is ¥30,630
¥71,011 total
includes taxes & fees
Mar 24 - Mar 25
New Tiny Home- Paddle Boards, Kayaks, Pool, Marina

Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

9.8 out of 10, Exceptional, (168)
"Clean, short walk to the beach or pool. Great place to stay."
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe

Cozy place in Calusa Key Largo

9.4 out of 10, Exceptional, (6)
"We enjoyed our time there it was very nice place. A really great rv park with a pool. And close to everything in Key largo "
The price is ¥23,435
¥50,024 total
includes taxes & fees
Feb 26 - Feb 27
Cozy place in Calusa Key Largo

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

9.6 out of 10, Exceptional, (101)
"If you are looking for an easy place to stay near Pennekamp State Park, this is a great option. Our family of 5 (4 adults 16 year old) enjoyed the great views and convenient location. It's small but adequate and had everything we needed for a couple of nights! "
The price is ¥48,202
¥92,871 total
includes taxes & fees
Mar 17 - Mar 18
Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

Welcome to Paradise!

9.6 out of 10, Exceptional, (57)
"We love Kawama and this unit and it's host are A. We hope to be back."
Welcome to Paradise!

Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

9.8 out of 10, Exceptional, (202)
"The unit was clean and had all the amenities that we needed. We had an issue with the shower and the owner was right on it to get it fixed. We would definitely recommend it."
The price is ¥44,781
¥83,629 total
includes taxes & fees
Mar 8 - Mar 9
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo

Mangrove Marina and Resort Aqualodge Houseboats

3.0 star property
9.4 out of 10, Exceptional, (327)
"We stayed in the Grey Lady and it was the perfect slip! Quiet, views of the bay/mooring field/mangroves. Limited kitchen amenities if you are "eating in". All staff friendly and helpful. WiFi sketchy."
Mangrove Marina and Resort Aqualodge Houseboats

Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

10.0 out of 10, Exceptional, (183)
"We enjoyed our stay can't think of any issues Defiantly would go back "
Completely Remodeled 3/3 in the heart of Key Largo (Oceanside)

Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

9.6 out of 10, Exceptional, (141)
"Best equipped condo ever, also nice firm mattresses. The only little glitch, was getting the keys out of the lock box. This could be replaced! We would love to stay here again!"
Oceanfront Property with Elevator, Lagoon and 2 Heated Pools

Beautiful Escape In Paradise

8.0 out of 10, Very Good, (3)
"Great location to get to everywhere we needed to in Key Largo!"
Beautiful Escape In Paradise

Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

9.8 out of 10, Exceptional, (38)
"Loved the property, location and amenities! The condo was exactly as advertised. "
Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys.

Amazing Ocean view at Ocean Pointe w/Heated Pool

9.6 out of 10, Exceptional, (28)
"We enjoyed our time together in this condo. It was clean, beds were comfortable and we enjoyed the pool and hot tub. It was easy to find and in a great area for good restaurants. We would love to go there again. "
Amazing Ocean view at Ocean Pointe w/Heated Pool
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 types of properties in Windley Key you may be interested in

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

3.5 star property
8.0 out of 10, Very Good, (1009)
"We did really enjoy this place. Room and property were clean. I was however frustrated and disappointed that the pool closes at 6pm. One of the things we enjoy most on vacation is swimming at night. 6pm? Way to expensive of a resort to not to be able to use the pool late in the evenings. This is nearly a deal breaker for our familly"
The price is ¥72,195
¥91,129 total
includes taxes & fees
Feb 26 - Feb 27
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Coconut Cove Resort and Marina

2.5 star property
7.4 out of 10, Good, (721)
"Great location and facilities along with very nice and helpful staff. "
The price is ¥45,527
¥51,218 total
includes taxes & fees
Feb 24 - Feb 25
Coconut Cove Resort and Marina

Fisher Inn Resort & Marina

3.5 star property
7.8 out of 10, Good, (1004)
"Close to the major highway "
The price is ¥34,855
¥44,091 total
includes taxes & fees
Mar 2 - Mar 3
Fisher Inn Resort & Marina
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.