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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
The exterior of the beach house is showcased, featuring a bright white facade and a unique geometric design on the railings. A spacious outdoor area is visible, adorned with lounge chairs and a shaded patio table, surrounded by crushed white stone and greenery.
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.
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 stars1 week 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
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
A bright kitchen area features a minimalist design with light-colored cabinetry and a countertop. A large window allows natural light to fill the space, while a framed beach scene hangs on the wall. Two stools are positioned at the counter, providing additional seating.
Home in Key Largo
4.84 out of 5 average rating, 50 reviews

Largo Sound Casita - Key Largo, Close to Pennekam

DanielRating, 5 stars3 weeks ago
The property is exactly as described. Perfect for families or a group of friends to go with the game room downstairs. Also provided is a binder with recommendations around the keys which was extremely useful.
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
A kitchen window displays a view of serene canal waters, accompanied by boats docked nearby. Decorative plants are positioned on the countertop, adding a touch of greenery. The sign above the window reads 'Marathon,' providing a local touch to the space.
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
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 private outdoor space is featured, showcasing a clear blue pool surrounded by lounge chairs and a dining area with chic striped umbrellas. Lush palm trees provide shade, while a stone pathway leads to the waterfront, enhancing the coastal ambiance.
Home in Islamorada
5 out of 5 average rating, 3 reviews

Islamorada Cay Home. Elegant home

MarlaRating, 5 stars2 months ago
The outdoor space is absolutely fabulous. The heated pool was enjoyed every day. The property is on the corner of two canals that had pretty clean water. We met several manatees who graced us with their presence often. Fishing was not great during the month so our fishermen were rather disappointed. The interior was very pleasant and cooking was easy. The entire third floor is the master sitting room, bathroom and bedroom. The only drawback for me personally is that the master bathroom is an "open concept " design which left me without a sense of privacy. Isa was extremely helpful and responded quickly with our questions. Thank you Isa!
Guest favorite
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 stars4 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
Tiny home in Key Largo
4.78 out of 5 average rating, 206 reviews

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards

KateRating, 5 stars1 month ago
Wish we stayed longer! We particularly enjoyed having the kayaks to go on self tours through the mangroves! Enjoyed the manatees off of the dock! Perfect stay, if we come back we’ll stay there much longer!!
Superhost
A golden statue of a mermaid stands near the edge of a clear blue pool, overlooking a canal lined with palm trees. Boats are moored at the dock, with the serene Atlantic visible in the background under a bright sky.
Home in Marathon
4.87 out of 5 average rating, 68 reviews

Oceanfront mermaid house pool and dock

PatriciaRating, 5 stars2 months ago
Greg's place was amazing! I loved being outside, sitting by the water, and looking out at the beautiful view. It is very quiet and peaceful, you feel like you are the only people around. We loved looking for sealife from the dock, and watching the boats go by the canal. The living room was comfortable and clean, and made a cozy place to enjoy the evenings. It was especially nice to have both bedrooms with their own ensuite bathrooms, and suited our two couples perfectly. I would stay here again in a heartbeat!
Guest favorite
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 stars5 days ago
We had 5 adults in our party. Plenty of room. Great space and location for fishing the keys and relaxing.
Guest favorite
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.
Top guest favorite
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 stars5 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
A crystal-clear pool is surrounded by lush tropical palm trees, lounge chairs, and umbrellas. The calm water reflects a clear blue sky, creating a serene atmosphere. This outdoor space offers ample seating for relaxation, with the ocean visible in the background.
Townhouse in Key Colony Beach
4.77 out of 5 average rating, 31 reviews

Manatee Quay-2 Canal waterfront,access BEACH club

DanielleRating, 5 stars2 months ago
Our stay at this home was absolutely perfect! The location couldn’t have been better—peaceful, relaxing, and right on the water. We spent so much time unwinding on the dock, soaking in the beautiful views and enjoying the gentle ocean breeze. The Marathon area was a fantastic place to explore, offering everything we needed for an unforgettable getaway. We loved being close to state parks for hiking and wildlife spotting, as well as having access to amazing restaurants serving fresh seafood. Bike rentals were nearby, making it easy to explore the area at a leisurely pace. If you’re looking for the perfect blend of relaxation and adventure, this is the place to be!
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 stars1 month 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.
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

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