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House vacation rentals in Windley Key

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Popular amenities for Windley Key house rentals

House rentals with a pool

Top guest favorite
Home in Marathon
4.99 out of 5 average rating, 133 reviews

Sea Ray Cove, Mini Lobster week NOW OPEN!

MauraRating, 5 stars4 days ago
We had an incredible week at Eddie’s place! The listing description and pictures matched our experience. Our favorite places to hang out were the screened in area, Tiki Hut, and by the dock. We fished off the dock daily and caught a great number of fish! We were also visited by a manatee. Eddie’s place is easily walkable to Sombrero Beach. The kitchen was well stocked and had everything we needed! We truly enjoyed this beautiful spot and would definitely book again on a future stay!
Guest favorite
Home in Key Largo
4.94 out of 5 average rating, 70 reviews

Casa Solaris | Key Largo home with Private Pool!

JessicaRating, 5 stars3 days ago
My family had a wedding in Key Largo and wanted a nice space to hold 6 people with a private pool. This place matched our needs perfectly! It's incredibly spacious, has amazing amenities and of course had the most beautiful pool and spa. I loved how there was a separate downstairs area with a kitchenette so my husband and I could have extra space as well. It was also close distance to restaurants and grocery stores. Sean always answered quickly and offered help if we ever needed it. It was the perfect house for our little getaway.
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 favorite
Home in Key Colony Beach
5 out of 5 average rating, 83 reviews

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

KarenRating, 5 stars3 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!
Superhost
Home in Key Colony Beach
4.83 out of 5 average rating, 12 reviews

P22 - Updated 3 bedroom 2 bath duplex with private

BrittanyRating, 5 stars31 months ago
We had six adults in our group and the house was a perfect location to go out fishing or to the beach. The house was well stocked and with plenty of linens and beach towels. We rented a boat for three days from Tropical boat rentals and the canal location made fishing super easy. Access to the ocean or the bay was convenient. We even caught several fish in the canal. We saw manatees, sharks, manna rays and tons of fish while enjoying the swimming pool. We can’t wait to make a return trip.
Guest favorite
Home in Marathon
4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars1 week 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!

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 stars9 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 favorite
Home in Marathon
5 out of 5 average rating, 11 reviews

Endless Ocean Views -5 Bedrm/4Bath/Pool Built 2024

ElaineRating, 5 stars2 weeks ago
Jessieca and her team are by far the most responsive and kindest hosts I've ever had on a rental. Beyond that, the place is beautiful and the sunset water views amazing. I see the price has gone up but if we can afford it, we will definitely return! You will have guests next to you and if they have children, you will probably be disturbed but that goes with the territory. Highly recommend this rental.
Guest favorite
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 favorite
Home in Marathon
4.92 out of 5 average rating, 49 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

MaxsenaRating, 5 stars1 week ago
Super nice place to stay. Very comfortable.
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.
Top guest favorite
Home in Marathon
5 out of 5 average rating, 37 reviews

Viva La Playa.Single family 3/2. Ocean view. New

BrigidRating, 5 stars2 weeks ago
We had a fantastic stay at Karen's place in the Keys! It perfectly suited the needs of our family of 5- 3 cute and cozy bedrooms, 2 full bathrooms, Beautiful and fully stocked kitchen, Washer/dryer to take care of beach towels and swim suits, Deck that overlooks the ocean that was perfect for morning coffee with the sunrise, and many more amenities. It was centrally located in the Keys to allow for travel from Key Largo to Key West in a little over an hour to each end. All in all, one of our favorite family spots, and we hope to one day visit again soon! Thank you so much!
Guest favorite
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 favorite
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 stars2 weeks 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.

Private house rentals

Guest favorite
Home in Marathon
5 out of 5 average rating, 17 reviews

Seaside Sunrise. Newly remodeled waterfront

JonathynRating, 5 stars1 month ago
Everything was excellent. Only complaint would be the bicycles. One bike was usable but the seat was loose and we didn’t have tools to fix it. The other adult bike’s chain was rusted so bad it wasn’t usable. We still had an excellent experience.
Superhost
Home in Homestead
4.88 out of 5 average rating, 42 reviews

Cozy Historic RelaxInn Close to AFB/Kro/Evergldes

JohnRating, 5 stars3 weeks ago
We thoroughly enjoyed our 3 night stay here! The house was very clean and had plenty of space for the 6 of us. There were lots of great amenities, but we loved the hot tub and outdoor dining area especially! We would definitely recommend this stay to anyone visiting the Everglades, and we would absolutely stay here again if we’re ever in the area!
Top guest favorite
Home in Key Largo
4.91 out of 5 average rating, 168 reviews

Blue House Marine in Key Largo

CharlieRating, 5 stars1 week 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 favorite
Home in Marathon
4.98 out of 5 average rating, 91 reviews

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

RobbieRating, 5 stars2 weeks ago
Amazing house. Beautiful surroundings. Plenty of room for 3 families and kids. Everything we needed.
Guest favorite
Home in Key Colony Beach
4.94 out of 5 average rating, 49 reviews

Waterfront House - 30' Dock & Pool & Cabana Club

LauraRating, 5 stars4 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 favorite
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 stars4 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.
Guest favorite
Home in Key Largo
4.8 out of 5 average rating, 50 reviews

Oceanfront Seaside Escape

PamelaRating, 5 stars2 weeks ago
This place was very peaceful and secluded. The only negative thing was the noisy construction during the day right next door. That is temporary though and for future guests not a problem. The scenery was breath taking and the kids enjoyed fishing on the dock. The rooms were clean and the house was designed for togetherness but also separate so you could have that option if needed. I would definitely choose this house again.
Top guest favorite
Home in Key Largo
4.89 out of 5 average rating, 123 reviews

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock

NathanRating, 5 stars2 weeks 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

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  3. Florida
  4. Monroe County
  5. Islamorada
  6. Windley Key
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