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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 Apartments in Windley Key and around

Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys
Private kitchen

Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys

9.8 out of 10, Exceptional, (10)
"The place was clean and had most of the things that would need. The second queen bedroom did not have a TV. That was the only downfall. Even though it was above the restaurant you did not hear anything."
The price is €452
includes taxes & fees
6 Apr - 7 Apr
Capt Craig's 2 Bedroom/1 bath Apartment in Tavernier, Florida Keys
Amazing Ocean view at Ocean Pointe w/Heated Pool
Terrace/patio

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
Hidden Gem Islamorada | 1st Floor
Pool

Hidden Gem Islamorada | 1st Floor

9.8 out of 10, Exceptional, (37)
"Great. "
Hidden Gem Islamorada | 1st Floor
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
Terrace/patio

Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball

9.0 out of 10, Wonderful, (83)
"Clean and cute. Great view of the ocean. We will be back"
The price is €533
includes taxes & fees
1 Apr - 2 Apr
Dazzling Ocean View Suite w/heated pool, beach, marina, tennis/pickleball
OCEANFRONT 2 BDRM, 2 BATH APT, KEY LARGO, TAVERNIER
On the beach

OCEANFRONT 2 BDRM, 2 BATH APT, KEY LARGO, TAVERNIER

10.0 out of 10, Exceptional, (129)
"Excellent unit just as advertised. Beautiful ocean view. Pool was amazing. Our host was very helpful appreciated dining recommendations. "
OCEANFRONT 2 BDRM, 2 BATH APT, KEY LARGO, TAVERNIER
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys
Fridge, microwave, oven, stovetop

Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys

9.8 out of 10, Exceptional, (18)
"Very nice property and place to stay - VRBO did not send check in details - thankfully the owner was on property. "
The price is €369
includes taxes & fees
8 Apr - 9 Apr
Capt Craig's 1 Bedroom /1 Bath Apartment in Islamorada, Florida Keys
Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
Property grounds

Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!

10.0 out of 10, Exceptional, (55)
"Lovely property.Great location. Host Lynn was very helpful."
Spectacular Open-Water Sunset Views w/Boat Slip & Trailer Parking. Pet Friendly!
Stunning 2BR/2BA Remodeled by interior designer-Dec 2024 Pool, Beach, Pickleball
Pool

Stunning 2BR/2BA Remodeled by interior designer-Dec 2024 Pool, Beach, Pickleball

10.0 out of 10, Exceptional, (4)
"We enjoyed our stay there"
Stunning 2BR/2BA Remodeled by interior designer-Dec 2024 Pool, Beach, Pickleball
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Marina

Sunrise Sanctuary - Top Floor Ocean Pointe 2415

9.2 out of 10, Wonderful, (7)
"Our condo couldn’t have been better! It was so clean and had plenty of room. I am a tea drinker and was so happy to see a teapot in the stove top! It’s those little things that make a place perfect! Our view was amazing from the tiny balcony. The pool at this complex was huge! We used it every day. The location was within a short drive to many great restaurants. I highly recommend this condo and want to come back soon!"
The price is €480
includes taxes & fees
30 Mar - 31 Mar
Sunrise Sanctuary - Top Floor Ocean Pointe 2415
Key Largo Cottages
Beach/ocean view

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."
Key Largo Cottages
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Property grounds

Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys

10.0 out of 10, Exceptional, (259)
"It was a nice Condo in nice area. Pictures represent property properly. Nice view, lovely pool. Only negative is the unit is on 4th floor and the elevator did not work the entire time we were there."
Ocean front 1/1,AMAZING OCEAN/MARINA VIEWS,Tavernier/Key Largo Fl. Florida Keys
Water View. Diver's Heaven. Fishing. Paradise Key Largo, Moonbay
Terrace/patio

Water View. Diver's Heaven. Fishing. Paradise Key Largo, Moonbay

9.8 out of 10, Exceptional, (68)
"Comfortable place, clean, easy to check in and out"
Water View. Diver's Heaven. Fishing. Paradise Key Largo, Moonbay
Waterfront Cabana 3
Smart TV, Netflix, streaming services

Waterfront Cabana 3

9.2 out of 10, Wonderful, (7)
"Cute, clean room and property. You won't be disappointed. Recommend to All. "
Waterfront Cabana 3
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Miscellaneous

Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!

9.8 out of 10, Exceptional, (68)
"Our host was very welcoming and friendly, and the accommodations were as represented on VRBO. The location was fantastic, we were able to travel easily to Key West and other things we wanted to see. Enough space to comfortably house 2 adults and 2 teens. We would definitely book in again on our next trip to the Keys."
Stay where you play, On the water w/Boat dock & Trailer parking. Pet friendly!
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
Terrace/patio

Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two

The price is €1,272
includes taxes & fees
31 Mar - 1 Apr
Ocean View Penthouse | Retreat amenities: tennis court, heated Pool | Vista Key Two
Treetops Studio · Sleep1-4 Beach Steps Away
Property grounds

Treetops Studio · Sleep1-4 Beach Steps Away

2.0 star property
The price is €305
includes taxes & fees
16 Mar - 17 Mar
Treetops Studio · Sleep1-4 Beach Steps Away
Hidden Gem Islamorada | 2nd Floor
Property grounds

Hidden Gem Islamorada | 2nd Floor

10.0 out of 10, Exceptional, (31)
"Since we were new to the area, we didn't know what to expect. Everything was wonderful. We especially liked the sitting area at the dock. Sean's communication about check-in, things to do, and restaurants was great. We will stay here again!"
Hidden Gem Islamorada | 2nd Floor
Starfish -1 bedroom 1 bath apartment with full kitchen in Islamorada, Florida.
Smart TV, books

Starfish -1 bedroom 1 bath apartment with full kitchen in Islamorada, Florida.

10.0 out of 10, Exceptional, (2)
"This had everything you need in a rental. Roomy and clean! We will definitely stay again!"
The price is €351
includes taxes & fees
8 Apr - 9 Apr
Starfish -1 bedroom 1 bath apartment with full kitchen in Islamorada, Florida.
Waterfront Cabana 4
Interior

Waterfront Cabana 4

9.6 out of 10, Exceptional, (9)
"Everything worked."
Waterfront Cabana 4
Waterfront House with Boat Dock at Florida Keys
Outdoor dining

Waterfront House with Boat Dock at Florida Keys

Waterfront House with Boat Dock at Florida Keys
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)
"Excellent water view"
The price is €208
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.