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Pet-friendly vacation rentals in Windley Key

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Windley Key pet-friendly home rentals

Pet-friendly house rentals

Guest favorite
A cozy bedroom features a queen-sized bed layered with soft linens. A flat-screen TV mounted on the wall displays a scenic beach view. Natural light enters through the window, covered by sleek shades, while storage options include a dresser beside the bed.
Home in Key Largo
4.94 out of 5 average rating, 144 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

TiffaniRating, 5 stars6 days ago
We absolutely loved our stay here! The place was spotless and had everything we needed. The location is incredible, right on the water. On our first night, we watched 12 manatees swim by from the porch. We also enjoyed using the kayaks, which was such a fun bonus. I can’t wait to come back and stay here again!
Guest favorite
A bedroom features neutral-colored walls and tiled flooring. A queen bed with a blue and white patterned blanket is positioned against the wall. Two windows allow ambient light, and a nightstand with a lamp sits beside the bed. A door leads to a bathroom area.
Home in Marathon
4.83 out of 5 average rating, 24 reviews

Dock Pool Ramp Jacuzzi Ocean Views Kayaks

HeatherRating, 5 stars2 months ago
House was nice and clean. Great location perfect for getting to open water. Frank was very helpful and responded quickly with any questions we had. I would recommend this place and would stay here again.
Guest favorite
A spacious outdoor area features a saltwater pool and a hot tub surrounded by lush tropical plants. A thatched tiki hut provides shaded seating, while a patio with lounge chairs is situated nearby. The home's façade is visible, highlighting large windows.
Home in Homestead
4.93 out of 5 average rating, 397 reviews

Private Paradise between Miami & the Keys

OliverRating, 5 stars1 week ago
Great home. The outdoor area was fantastic and the kids loved the pool. BBQ area was perfect for the evenings. The house itself is very spacious and has everything that you need. Perfect for a family getaway, close to the Everglades and the keys
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 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 favorite
Home in Key Colony Beach
4.95 out of 5 average rating, 112 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

JessRating, 5 stars1 week ago
We loved our stay! The house was super clean and the back patio was beautiful. We loved the back canal area and saw lots of very cool wildlife and enjoyed fishing right there. Having the kayaks to use was also great. Beds were very comfy and the rooms were spacious. The house had everything we needed. We loved the key colony area. The cabana club was a great space and the house is in walking distance to Sunset Beach, which was beautiful. The whole area is super close to fun things to do and great restaurants. We would absolutely stay here again!
Guest favorite
This master bedroom features a spacious bed covered with a quilt and a cozy seating area with a sofa. Large windows allow for natural light and views of the outdoors while the wood paneled ceiling adds warmth to the room.
Home in Marathon
4.98 out of 5 average rating, 50 reviews

Waterfront Private Home w/Pool-Family&Pet Friendly

Dan & RachelRating, 5 stars1 month ago
This was an awesome home for our family of 4 + dog. We felt right at home for the week! The pool was perfectly warm, and the kids had so much fun playing by the dock. We rented a pontoon boat and were able to dock it easily. Honestly, we hardly used the other amenities in the home because the weather was so nice, but if it rained we probably would have loved the game room too! Overall this was a great home for our family. The neighborhood isn’t super walkable, but the grocery store was just down a little footpath, allowing us to walk to get groceries as needed. Loved this!
Guest favorite
Home in Homestead
4.97 out of 5 average rating, 29 reviews

Centrally located Family\business Home

NatasshaRating, 5 stars2 days ago
We have stayed at Jennifer’s place before and it’s just as lovely as before! Jennifer is a great host; responsive, friendly and communicative. Definitely recommend her place and look forward to coming back soon! Thank you!!
Guest favorite
A canal dock extends alongside the property, featuring wooden decking and a swimming ladder for easy access to the water. Lounge chairs are positioned nearby, and tall palm trees provide a tropical ambiance. The clear blue sky reflects off the tranquil water.
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 stars1 week 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.

Pet-friendly home rentals with a pool

Superhost
A modern kitchen features white cabinetry and stainless steel appliances. A wooden cutting board is placed on the counter, complemented by cooking utensils. Soft lighting illuminates the space, enhancing the clean and functional design. A window with shutters allows natural light to enter.
Condo in Key Largo
4.94 out of 5 average rating, 101 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

KarenRating, 5 stars3 days ago
This place is a great place for families. All ages can enjoy this neighborhood. It’s close to everything, but it feels cozy.
Superhost
Villa in Marathon
4.95 out of 5 average rating, 136 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

StefanieRating, 5 stars2 weeks ago
My family and I stayed for a week and the house had everything we needed and more! The space was clean, comfortable and had lots of extras for the outside like pool floats, bikes, paddle boards, kayaks and more. The added touches inside like dish soap, hand soap, cleaning supplies, shampoo and conditioner was unexpected and a huge help. I was slightly surprised that this was an attached home, but there was still plenty of privacy and the location was extremely convenient. The hosts were very friendly and responsive and we would definitely recommend to others.
Superhost
An aerial view of a vibrant waterfront neighborhood showcases a pale yellow house surrounded by lush greenery. Nearby, several homes with varying colors and styles line the streets, while a deep canal runs at the back, providing easy waterway access.
Home in Key Colony Beach
4.82 out of 5 average rating, 11 reviews

Key Colony Beach-POOL & DOCK

RichardRating, 5 stars4 days ago
We had 5 adults in our party. Plenty of room. Great space and location for fishing the keys and relaxing.
Superhost
A spacious living area features a large gray sectional sofa adorned with decorative cushions. A round coffee table is positioned in front, and a colorful painting of a boat enhances the wall. Natural light streams in through glass doors leading to an outdoor seating area.
Home in Marathon
4.88 out of 5 average rating, 24 reviews

Golf Coast Oasis

AmandaRating, 5 stars4 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!
Superhost
Home in Homestead
4.91 out of 5 average rating, 45 reviews

Slice of paradise near Everglades & Key Largo

ClaireRating, 5 stars2 weeks ago
We loved our stay at Jose’s place! The outside space was amazing, with plenty of space to sit, dine, cook and with the added benefit of the pool. Inside, there is a well stocked kitchen, very comfortable beds with high quality bedding, two bathrooms and a large couch / tv area. It’s a spacious property with plenty of space for 4 visitors. The house was full of character and it was fun to stay there. Recommended.
Superhost
An inviting outdoor space is showcased, featuring a swimming pool framed by comfortable seating arrangements. A large canopy provides shade, while a barbecue grill is placed nearby. Surrounding greenery adds a touch of nature, enhancing the overall relaxing environment.
Home in Marathon
5 out of 5 average rating, 10 reviews

Sunset keys villa w/Den, pool, Firepit &Boat space

MichelleRating, 5 stars1 month ago
Everything about Lazaro’s stay was 5 Star!! He was easy and friendly to communicate with and went above and beyond to make our stay a delight. The property itself was perfect. Everything is brand new and it was one of the best stocked places I have stayed, from the decor to the spacious layout to the stocked cabinets. The fully fenced yard was perfect for our dogs who enjoyed it very much. The location is on a quiet street in the heart of Marathon with so much close by. Ideal!! Truly a 5 star stay and highly recommended.
Superhost
A bright bedroom is presented with large windows offering views of the outdoors. The spacious bed is adorned with a light gray throw blanket and decorative yellow pillows. A textured basket sits in one corner, enhancing the room's functionality and aesthetic.
Home in Key Colony Beach
5 out of 5 average rating, 9 reviews

Cielo's Del Mar 2 - Pool / Dock / Beach Luxury in KCB

JoAnnRating, 5 stars4 days ago
What a fantastic house! Close to the beach, great options for activities and food nearby. The house was clean and well-equipped and even more beautiful in person. Our family enjoyed quiet days at the house to relax and enjoyed local swimming, snorkeling, and shopping. Pool was clean and a nice respite. We did heat the pool for the week which was worth it!

Private, pet-friendly home rentals

A serene sunset casts warm hues over calm waters, reflecting shades of orange and pink. Silhouetted against the horizon, two individuals are seen paddling a small boat, while the coastline is dotted with distant, dark outlines of land and rocks.
Home in Key Largo
4.76 out of 5 average rating, 74 reviews

Beautiful FL keys Home-Free Bike to use

JoeRating, 5 stars1 month ago
Nice place to stay in Key Largo, close to Tavernier end of Key. Long ride if going to Key West. Nice little patio in back on second floor. Easily sleeps 6. Nice kitchen. Easy to park in front Yard. Nice stay. Snappers restaurant easy walk across Rt 1. Joe L.
A well-maintained outdoor area features a round table surrounded by white chairs. Lounge chairs with green cushions are positioned nearby, under teal umbrellas. A white picket fence borders the area, providing views of the water beyond.
Home in Key Colony Beach
4.78 out of 5 average rating, 18 reviews

2BR Oceanview Dog Friendly | Pool | Dock | Deck

LilianaRating, 5 stars16 months ago
We had the perfect vacation! Love the location and the amenities of Key Colony Beach. The place was great for relaxing. I only wish we brought our dog..
Superhost
The open layout features a spacious sleeping area with a king-size bed decorated in blue and white patterns. A cozy sitting area includes a large sofa, while a dining table is visible in the background, complemented by cheerful green walls and tropical-themed decor.
Cottage in Key Largo
4.77 out of 5 average rating, 13 reviews

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

KlaraRating, 5 stars1 month ago
We really enjoyed our stay with Key Lime sailing club! We especially appreciated the easy access to water activities and created life long memories kayaking in the beautiful surroundings. The hosts are kind, helpful and made our stay more memorable!
A two-story home with a light blue exterior is complemented by a heated pool surrounded by a lounging area. Lush greenery and a palm tree frame the space, providing a serene atmosphere. The patio below is equipped with ample outdoor seating for relaxation.
Home in Key Largo
4.81 out of 5 average rating, 21 reviews

Waterfront Key Largo Home - Tropical Paradise

CarolineRating, 5 stars1 month ago
This was our first time back to the Keys in over 20 years and I could not have picked a better spot. The neighborhood is quiet and neighbors friendly. Having our boat just outside the door for a quick boat ride or heading out for a day of fishing was extremely convenient. There is electricity and water at the dock which was great for charging the battery. We had a sweet manatee come visit us one morning which everyone loved. The house is beautifully decorated and makes you feel like you are on vacation. The couch, beds, and pillow were so comfortable it was easy to fall asleep and hit the snooze button in the morning. My favorite spot, however, was the wide, breezy veranda where we all spent time reading and watching the boats go by. To top it off we had our own private pool to lounge in after an excursion on the water. We will definitely book here again for our next stay!
Top guest favorite
An aerial view captures a vibrant coastal community surrounded by water, featuring a marina filled with boats and lush greenery along the shore. A well-maintained pool area is visible, offering a serene setting for relaxation amidst the palm trees.
Camper/RV in Key Largo
4.97 out of 5 average rating, 37 reviews

Paradise Key Largo

DeannaRating, 5 stars4 weeks ago
Our family of 5 just returned from vacation. My toddlers loved the pool and all the hammocks near the water. Niurka was responsive to any questions we had and gave local recommendations on where to take the kids. We had a great time and will definitely return.
A landscaped outdoor area is showcased, featuring an inviting lawn bordered by tropical plants. Two colorful cornhole boards are positioned on the lawn, and a path of paving stones leads to the side of the home, enhancing the outdoor space.
Home in Marathon
4.58 out of 5 average rating, 12 reviews

Walk to Beach 4BR | Dock | Dog Friendly | Pools

HayleyRating, 5 stars10 months ago
Just want to write an updated review since most of these are older. The previous reviews about the house AC being hot in the downstairs bedrooms has been fixed. The house has two brand new AC units. House was immaculate and in the perfect location with all the amenities you’d need. Only issue we ran into is the Wi-Fi does not work. They are actively working on it but the Sonos speakers did not work outside and the TVs were in and out. All in all this house had everything we needed and more
Superhost
A spacious room features a bed draped in a blue and white floral bedding set. Large windows offer views of the outdoors, with a small dining table and chairs visible on the balcony. A compact refrigerator is positioned near the entrance, enhancing convenience.
Apartment in Big Pine Key
4.8 out of 5 average rating, 41 reviews

Apartment in Big Pine

MalloryRating, 5 stars1 week ago
This little studio apartment in big pine is PERFECT for a couple for a few days or week. We loved the big windows on 3 sides, with a great view of sunset & the marsh. We also loved the private and spacious balcony that has a view of sunrise. It is very peaceful and quiet, with the deer coming by every morning and evening. There is no kitchen (which was fine with us) but there is a coffee pot and 2 mugs. The bathroom is roomy for a studio and has closet space available. The sunset view from this place honestly was my favorite part of our trip. I would stay here again if I traveled to the keys in the future.
Guest favorite
A wooden dock extends alongside a peaceful canal, surrounded by lush greenery and vibrant flowers. A small circular mat lies on the edge, while a decorative light fixture stands elegantly on the dock. Boats can be seen moored in the distance under a clear blue sky.
Home in Marathon
4.96 out of 5 average rating, 23 reviews

Gulf side Gem, 45 ft. dock, pool, Hot tub and more

VanessaRating, 5 stars1 week ago
We truly enjoyed our stay. Gail was very communicative and the house had everything we needed to relax and enjoy our time. We saw some manatees from the dock, iguanas, and of course fish. Friendly quiet neighborhood, grocery store close by.

Destinations to explore

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  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Windley Key
  7. Pet-friendly rentals