
Pet-friendly vacation rentals in Windley Key
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Top-rated pet-friendly home rentals in Windley Key
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Popular amenities for Windley Key pet-friendly home rentals
Pet-friendly house rentals

Seaside Sunrise. Newly remodeled waterfront
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.

Tiny Home on Waterfront | Bay Views | Deck | Pool
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!

Waterfront House - 30' Dock & Pool at Cabana Club
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!!

Waterfront Home 37.5-ft dock, Cabana Club Included
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!

Largo Sound Casita - Key Largo, Close to Pennekam
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.

Waterfront Private Home w/Pool-Family&Pet Friendly
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!

Blue Ocean Bungalow Spring discounts-NOW available
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

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

Islamorada Cay Home. Elegant home
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!

Gorgeous lagoon-front 2BR Townhouse with 2 pools
This place is a great place for families. All ages can enjoy this neighborhood. It’s close to everything, but it feels cozy.

Waterfront Beach, Pool, Dock, Kayaks, Paddleboards
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!!

Oceanfront mermaid house pool and dock
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!

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

Key Colony Beach-POOL & DOCK
We had 5 adults in our party. Plenty of room. Great space and location for fishing the keys and relaxing.

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

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

Beautiful FL keys Home-Free Bike to use
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.

2BR Oceanview Dog Friendly | Pool | Dock | Deck
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..

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

Waterfront Key Largo Home - Tropical Paradise
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!

Paradise Key Largo
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.

Apartment in Big Pine
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.

Waterfront, dog-friendly 4BR with great canal view
Very comfortable and an amazing view of the canal. We could walk right off the deck and out along the boardwalk for the canal. Gorgeous for sunrises.

Gulf side Gem, 45 ft. dock, pool, Hot tub and more
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.
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- Everglades National Park
- Anne's Beach
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Bahia Honda State Park
- Zoo Miami
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Biscayne National Park
- Cannon Beach
- Far Beach
- Monkey Jungle
- Windley Key Fossil Reef Geological State Park
- Deering Estate
- Sea Oats Beach
- Theater of the Sea
- Cocoa Plum Beach
- Sandspur Beach
- EAA Air Museum
- Everglades Alligator Farm
- Keys' Meads
- Long Key State Park
- Horseshoe Beach