House vacation rentals in Windley Key

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Windley Key house rentals

House rentals with a pool

Top guest favourite
Home in Marathon
4.99 out of 5 average rating, 132 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

StephenRating, 5 stars3 days ago
We had a great time during our one week stay. The location was perfect! Easy walk to the beach and beautiful canal views. We loved our visits from the manatee! We spent our days outside exploring the Keys and it was lovely to return each evening to this great house. We grilled dinners and enjoyed meals on the screened porch. Sunrise over the canal was gorgeous. We were sad to leave!
Guest favourite
Home in Key Largo
4.94 out of 5 average rating, 68 reviews

Casa Solaris | Key Largo home with Private Pool!

JeffRating, 5 stars4 days ago
I am typically not an Airbnb person, as I prefer a hotel. This home was better than any resort we could’ve stayed at. Check in was simple. The home was beautiful. The location was perfect. Our favorite part was the second space that was separate from the main house. We are a family of four (mom, dad and two kids) who were traveling with my sister. She was able to have her own space with a private bathroom and entrance and could “go home” when the craziness of two kids was enough. Both units were adequately stocked with towels and linens. The kitchens had anything you could need including coffee maker, blender, toaster, pots and pans. The pool and hot tub were incredible! So much so, that we took two full days and only left for dinner! Sean and Denise were great hosts and super responsive! We will be back.
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars3 months ago
We had a great time at Cary’s Oceanside! Beautiful location, beautiful and comfortable accommodations! Maria was very helpful and responsive with our questions. We really enjoyed the pool and outdoor area.
Superhost
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars5 months ago
Stunning location, very comfortable with plenty of space for 10 people. When we arrived we never felt like leaving. Beautiful pool and hot tub surrounded by palm trees, sandy area with great fire pit, gorgeous outdoor eating area and kayaks to drop from pier. Very private location with spectacular sunsets! Fabulous!!!!
Superhost
Home in Islamorada
4.86 out of 5 average rating, 7 reviews

Venetian Tropics private heated pool at 82 degrees

JessicaRating, 5 stars7 months ago
I’d like to start this review with JoAn is amazing and super responsive. If you need anything, she will ensure that you will get it. This house is the epitome of what you would expect for a Florida keys home. If you’re looking for a house with a lot of character, in a phenomenal location for Atlantic access and fuel, this is the place. We throughly enjoyed our time staying here and will be back next year. The pool was nice to get into after diving every day, there was a fresh water hose on the dock, a freshwater outside shower and even a fish cleaning station. There is a deep freezer for ice and a tiki bar outside with a sink. Couldn’t be any happier with the house or the host. Thanks again JoAn for letting us use your house.
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 83 reviews

“La casa azul” step 3’ to a private pool

KarenRating, 5 stars2 weeks ago
We throughly enjoyed our stay. We especially loved the private pool and watching the wildlife and boaters in the canal. It was very relaxing and the Florida spring weather was awesome!
Guest favourite
Home in Marathon
4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars3 days ago
This was the most perfect Airbnb for our vacation. First of all, Marathon is the perfect location if you are looking to explore multiple parts of the Keys. 1 hour to Key Largo, 1 hour to Key West. We could not have asked for a better location. The home looks just like the photos and was perfect for our family of 4 + our pup. The beds were comfortable, the living space had plenty of room for our crew, but the real show stopper was the pool. If we weren't out and about exploring the Keys, we were definitely in/by the pool! A few added bonuses: (1) K-cups for our use for that first morning. This kept us from having to worry about an emergency grocery store trip the evening of our arrival (2) pool floats available for our use (3) bikes & kayaks for everyone (4) EVERYTHING. We couldn't have asked for better - we will definitely be back!
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 112 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

JessicaRating, 5 stars1 week ago
Our family of 9 loved the house! The pool, corn hole, and roof deck were all huge hits with the kids. The house is perfectly situated on Marathon, close to all the restaurants. Quick drive to Bahia Honda. We will definitely will be back for another visit to Andy’s place.

Weekly house rentals

Superhost
Home in Key Colony Beach
4.74 out of 5 average rating, 23 reviews

Private Beach, Deep Water Dockage, Cabana Club

GregRating, 5 stars8 months ago
Roberto is by far the most thorough and conscientious host. We were so pleased with our accommodations and immediately felt at home. The use of The Cabana Club was a real bonus on the hottest days. Will most certainly return to Marathon!
Guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Yellowtail Getaway with Boat Dock and Pool 2

HopeRating, 5 stars1 month ago
We absolutely loved the place , it was spacious , clean and had all the extras you would need. So convenient with the boat dick and loved having the pool. Would definitely return.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 47 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

RebeccaRating, 5 stars1 month ago
Giselle and Javier were awesome with communication, they gave us a ton of recommendations for food and we tried out almost all of them. Some of the best food we’d ever had and a lot of them were within walking distance of the house! The house was perfect, light, clean, and modern. We were able to catch fish off the dock and even saw a few manatees come through. Probably the best Airbnb we’ve stayed in overall!!
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Sailors Paradise

CrystalRating, 5 stars1 month ago
Sailors Paradise was a very nice, clean with a quiet neighborhood. The house was comfortable. The back area was very relaxing with the channel right there. The kitchen had plenty of counter space. Water pressure in shower was good. Water got hot quickly. All in all a great place. I would definitely recommend it.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 69 reviews

Blue Ocean Bungalow Spring discounts-NOW available

HixRating, 5 stars1 month ago
The house was really nice, clean and a real home away from home. It accommodated my family of 5 with 3 bedrooms and 3 baths. It was located on a canal where we were able to enjoy the manatees and pelicans. It was centrally located and only a short distance from the beaches, snorkeling, wind surfing and excellent restaurants. We will definitely stay again if we visit the keys
Guest favourite
Home in Key Colony Beach
4.91 out of 5 average rating, 135 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

NicoleRating, 5 stars6 days ago
We didn't know anything about Key Colony so based our reservation strictly on reviews and price. Well worth every penny that was spent. What a wonderful tropical getaway! Can't wait to visit the Keys again with my 4 children and husband. If you're looking for a great place to spread out and enjoy family this should be your rental.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 68 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

ChrisRating, 5 stars1 month ago
We had a great stay here, beds were comfortable and bathrooms were clean. Kids loved fishing off the dock - although the boat ramp was unavailable, we were able to use the ramp at the marina down the block ($30 each drop). Hosts were easy to communicate with and very helpful when we had a question. Wed definitely stay here again next time in Marathon.
Guest favourite
Home in Key Colony Beach
4.86 out of 5 average rating, 7 reviews

Seas the Day

BernardRating, 5 stars1 month ago
We really enjoyed it here. The boat dock was perfect, easy access by water to gulf, ocean, and local restaurants. The inside was cozy and comfortable. All necessary household items/appliances were provided. There was parking in front and additional parking across the street. There was room in the driveway for a small boat trailer. Guest membership to the Cabana Club was especially nice with access to the beach, pool, hot tub and restaurant/bar. This location is conveniently located within a short ride to stores, shops, restaurants, and local attractions. Overall, this is a very nice rental property and the price was reasonable. We would definitely consider staying here again in the future.

Private house rentals

Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 44 reviews

Florida Keys Retreat / Completly remodeled

SeanRating, 5 stars3 days ago
Perfect for our family of 5. Great outdoor area at the house for fishing and relaxing. The layout was great for us because of the separation from the master to the kitchen/living room…our baby could sleep and we didn’t have to worry about making noise and waking up the baby. KCB is in a great central location for exploring the Keys. We were also pleasantly surprised at the quality of restaurant’s nearby. The Cabana Club was crowded and has a small beach. Drinks there were good. I have nothing overly negative to say, other than that I wouldn’t look to stay in KCB or this property if you just want to hang at the pool and beach all day. But it was fine for a few easy afternoons between other activities in the area. We highly recommend and would stay again!
Guest favourite
Home in Key Colony Beach
4.99 out of 5 average rating, 106 reviews

ABeachBungalow-60’dock w/ access to pool and beach

JosephRating, 5 stars1 month ago
Very cozy and clean! Access to the Cabana Club (private beach club with pool, bar, and restaurant) makes it worth the price. Excellent hosts as well.
Top guest favourite
Home in Key Largo
4.91 out of 5 average rating, 167 reviews

Blue House Marine in Key Largo

CharlieRating, 5 stars2 days ago
We had a Great stay ! Location was perfect for our dive plans ! Also a wonderful restaurant just around the corner for an easy walk
Guest favourite
Home in Marathon
4.98 out of 5 average rating, 91 reviews

4BR 3B, Heated Pool & Spa, 60' Dock

RobbieRating, 5 stars1 week ago
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.
Guest favourite
Home in Key Colony Beach
4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool at Cabana Club

LauraRating, 5 stars3 months ago
We will be back! We loved it! Clean, comfortable with lots of room. We loved being able to keep our boat behind the house and the trailer in the driveway. We loved walking around Keys Colony. The Cabana Club and Sparkys Restaurant were both within walking distance. The kitchen had every gadget you could imagine. The dining table was perfect for dinners and card playing. The beds were comfy. No allergies whatsoever! Thank you so much!!
Guest favourite
Home in Key Colony Beach
4.95 out of 5 average rating, 42 reviews

Casa Lago Mar 3/2 with Cabana Club Access

TimRating, 5 stars3 months ago
We loved staying at Melissa’s Airbnb. The neighborhood was nice and very walkable. Loved being right on the canal. The Cabana Club was great for kids with the pool and beachfront area. Marathon was a great Key to stay on with lots to do. The duplex was clean and beds were comfortable. Loved sitting out on the back porch in the morning with coffee. We would definitely recommend and would love to come back someday.
Superhost
Home in Key Largo
4.8 out of 5 average rating, 92 reviews

Paradise Found-Key Largo Kampground Divers Welcome

StevenRating, 5 stars3 weeks ago
Veronica was very responsive . We were late arriving due to flight delays and she helped make arrangements for us to check in. The house was very clean and centrally located for everything we wanted to do at Key Largo. We would definitely stay here again.
Guest favourite
Home in Key Largo
4.89 out of 5 average rating, 123 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

NathanRating, 5 stars6 days ago
We had a great time visiting the FL keys and staying on Mangrove lane. It was awesome hanging on the dock, using the pool, fishing, and catching the sunsets each night. We also really enjoyed having the screened in porch upstairs and spent our breakfasts and night cap cocktails out there. Great spot on a private street! Looking forward to coming back in the future.

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Windley Key
  7. House rentals