Set within the popular beach destination of Florida Keys, to the south of Key Largo, is the mesmerising destination of Islamorada. Comprising four islands, Islamorada is aptly known as ‘Village of Islands’. With its quiet ambience, it provides the perfect setting for a laidback tropical getaway. The region is famed for its sport fishing which attracts fishing enthusiasts throughout the year. While its beaches remain its main attraction, visitors should not miss checking out the marvellous sea life found around here. Scuba diving, snorkelling and boat rides are great ways to appreciate the area’s diverse marine life. Theater of the Sea, Keys History & Discovery Center, and Lignumvitae Key Botanical State Park are some of the main attractions. If you are planning a vacation here and want to take your furry friend along, check out our curated list of pet-friendly Airbnbs in Islamorada, Florida.
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and pet-friendly rules and regulations. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Oceanfront oasis with beautiful private beach
An ideal option for large groups or families travelling together, this sprawling house offers its own private beach, plentiful outdoor amenities and elegantly furnished interiors. With five bedrooms, the property can host up to twelve guests. The house follows a large open floor plan that includes a living room and a dining area facing the ocean.
The house has a fully equipped kitchen. Outside, a full-sized swimming pool and ample patio furniture are available to the guests. The surrounding garden comes with a gazebo and leads to the beach. Pets are welcome, and your dog will surely enjoy a swim in the sea.
Islamorada, Florida, United States
50.36 km (31.3 mi) from Everglades National ParkAccommodates: 10
Top guest reviews
Amenities & Room:
they really want you to be comfortable and aware of all that the area has to offerRead more reviewsLocation:
great location and perfect for families that want to spend their time outside
2. Trendy beach home with dock access (from USD 514)
Featuring chic styling in a coastal palette, this beach home, located within a residential community in White Marlin Beach, offers a gorgeous setting for up to eight people. A large open-plan living area comprises a full kitchen, a sitting section and a dining area. The house provides four bedrooms, spread over two floors.
Its outdoor amenities include direct access to a dock, a pool, a wooden deck, access to a private beach and ample lounge furniture. Pets are allowed with prior approval, and extra charges are levied per pet. Additional requirements include documentation such as veterinary certification and more according to their pet addendum.
Top guest reviews
Amenities & Room:
there is plentiful sheltered & comfortable outdoor living space & we spent most of our time outsidethe decor is comfortable and beach chic without being theme-yCleanliness:
the beds were very comfortable and house was clean and equipped with everything we neededadriana’s home is beautiful everything was clean and as pictured5 stars aren’t enough for this relaxing clean well-designed and well-though out homeHost:
adriana was a responsive friendly host and we are already planning our returnRead more reviewsLocation:
great location in lower matecumbe on a canal with easy access to the gulf and atlanticgreat location beds were comfortable the house had everything you needed for a fantastic stayreally charming cottage in a really great locationislamorada is the perfect place to stay for a visit to the keysadriana's place was perfect for our family and we'll appointed
3. Flakey's (from USD 275)
This charming rental is located right in the heart of downtown Islamorada on Morada Way. It is situated on the upper floor of a property with the ground level housing a brewery tasting room. Upstairs is completely private and quiet, with the rental providing two bedrooms. The entire unit can comfortably host up to six persons. A large open-plan living area comes with a lounge area, a kitchen and a dining section.
Two balconies set up with patio furniture are available. Guests can also access a large backyard garden that is shared with the brewery. Pets are welcome and a separate deposit is applied.
Top guest reviews
Amenities & Room:
the bathroom has hidden heater for your bathing comfortwe had a front row seat from the comfortable balconyit was decorated with comfortable cozy furniture and the bed was so comfortablethe a/c felt amazing after a long hot day of fishingthe beds were so comfy as wellCleanliness:
so clean and comfyit was so clean and neatthe apartment is clean and easythe apt is spacious clean and well appointedthe apartment was so spacious and spotlessly clean on arrivalHost:
the host was super friendly and accommodatingflorida brewery downstairs and the staff were awesomeour hosts were very nice and accomodatingshe is very attentive and easy to reachall in all a wonderful host with a wonderful home hopefully be back soonRead more reviewsLocation:
great place central to everythinggreat location better than we expectedbeautiful space and central to everything on islamoradawe were able to walk to great restaurants and shoppingbest location in islamorada close walk to restaurants breweries and markets
Superhost
4. Waterfront house by canal (from USD 499)
Newly remodelled, this two-storey house within a residential community comes with five bedrooms that can sleep up to twelve guests. Situated by a canal and surrounded by lush mangroves, the property offers a quiet, tranquil vibe.
On the ground floor, there is a capacious open-plan living area that comprises a lounge area, a dining area and a fully stocked large kitchen. The space is lined with windows, giving the room a radiant feel. Adjoining it lies a deck with ample outdoor furniture. The upper level has a balcony. Two bedrooms are available on the ground floor, and the remaining three are on the top floor. Pets are welcome and an extra cleaning fee is applicable.
Top guest reviews
Amenities & Room:
large comfortable back porch overlooking mangrove and a canalthe beds were comfortable on the upper level and the bathrooms were nicely maintainedwe enjoyed the pool table in the basement and liked the grillwe had a great time downstairs as well playing pool and other games availableHost:
the host was wonderful answering all our questions before and during our staybarbara was a wonderful hostdecorated nicely and host sent list of local attractionsthe owner was very responsive to any needs/concerns during our stayit was perfect the hosts are great and easy to book withRead more reviewsLocation:
perfect location for our diving tripgreat location close to many restaurants and other thingsbeautiful home in a great location in the keysclose to many great restaurants and other things to do in the keysawesome house the neighborhood is beautiful great for walks
5. Tastefully decorated holiday house (from USD 325)
This beautifully furnished house features graceful coastal-style decor and premium amenities. It is spread over two levels and comes with four bedrooms that can sleep up to eight persons. The interiors include an open-plan living-cum-dining space, a kitchen and a lounge area.
Outside, an enclosed porch overlooking a garden as well as a swimming pool and a deck are open to guests. The upper level offers a balcony, and guests have use of a dock. Pets are welcome!
Top guest reviews
Amenities & Room:
the heated pool was great to haveCleanliness:
the place is as advertised very clean and well maintainedHost:
yanelis was very accommodating and responsiveRead more reviewsLocation:
the location is wonderful but it might be important to clarify what supplies you need to bringgreat location great home loved our family vacation here will be back for surelocation is the best i used to live in the keys - so was familiar with the area
6. Keys Kottage (from USD 290)
Set amid a lush garden, this cute cottage faces Florida Bay and offers great views. It comes with a living room, an open-plan kitchen-cum-dining area and two bedrooms. The villa can comfortably sleep up to four guests.
A deck is available outside that overlooks the garden and is set up with lounge chairs. Additionally, dockage and a boat trailer parking space are available for guests. Furry friends are allowed!
Top guest reviews
Cleanliness:
the villa was very well equipped and cleanRead more reviewsLocation:
great place to stay close to anything you might want or needthe place is very cozy and the location is great to some fabulous waterfront bars and restaurants
7. Guest suite with beautiful garden
This snug rental unit is a fantastic choice for couples or solo travellers. The property offers a sitting room, an open kitchen with a dining table, and a bedroom with a double bed.
A patio outside provides views of the bay and has been set up with sufficient garden furniture and grills. Kayaks and snorkelling gear are available at no extra cost. Pets are welcome, though cats may not enjoy kayaking!
Islamorada, Florida, United States
50.43 km (31.4 mi) from Everglades National ParkAccommodates: 2
Top guest reviews
Amenities & Room:
lots of space and bed new and comfortableangie was kind enough to let us borrow her personal fanhowever shower tiles looked new and very cleanthe property is 100% prime space plenty of room to spread out or be friendly to other gueststhe apartment was beautiful and our stay was fantasticCleanliness:
space was clean and just as describedangie had it sparkling clean when we arrivedit is clean comfortable and coolcomfortable and cleanthe unit was cozy and clean and had everything we neededHost:
kevin was such a lovely hostkevin was welcoming and helpfulkevin is a great host and very accessiblehosts are very helpfulthe host was super friendly and helpfulRead more reviewsLocation:
absolutely loved the locationbeautiful location right on the watergreat location very fun kayaking and cool fish and lobsters you can seeperfect location with beautiful private beachthe terrace and the location are the best u can wish for
8. Islamorada Ocean Oasis
Enjoy a stay surrounded by luxury at this large house that comes with a private beach. The house is spread over two levels. The ground floor has a sitting room, a kitchen and a dining space, as well as two bedrooms. The upper level comes with a well-furnished lounge area, a fully equipped kitchen and a formal dining space. The remaining three bedrooms are found here as well. In all, the house can accommodate up to 14 guests.
The property’s outdoor amenities include a heated pool, a hot tub, a deck and private beach access. Dogs below 35 lbs (15.8 kg) are allowed, and a nightly fee is applicable.
Islamorada, Florida, United States
50.6 km (31.5 mi) from Everglades National ParkAccommodates: 14
Top guest reviews
Amenities & Room:
the pool area is beyond what the pictures show perfect for lots of hanging out and relaxingamazing house in islamorada comfortable rooms and beautiful sceneryCleanliness:
it was clean stocked and very spaciousthis house is sparkling cleanclean and neat megan was very helpful got back to us right awayHost:
home owner and the property manager were very quick to respond and very helpful when we had questionsgreat host and an amazing placevic our host was terrific responsive and responsibleRead more reviewsLocation:
great location a few mins from everything around islamoradaoverall a wonderful place to stay
9. Appealing apartment with pool access
Bright and welcoming, this beach house-style apartment is located close to a dock. It offers two bedrooms that can sleep up to four persons. The large open-plan common area comes with a living room, a small kitchen and a dining area.
The outdoor amenities include a swimming pool, a garden and a porch. Additionally, a gazebo adjoining the dock is available for guests’ use. Pets are welcome!
49.44 km (30.8 mi) from Everglades National ParkAccommodates: 4
Top guest reviews
Amenities & Room:
so much room to spread out and relaxthe beds were very niceplace was exactly as described pool was amazinggreat place to stay if you’re looking for a quaint cozy old-florida style propertythe bedroom was just the right size and the bed was comfortableCleanliness:
the place was very clean and had everything we neededthe pool area was nicely done and he kept it clean and invitingthere was plenty of everything in the apartment for cooking cleaning laundry was easily accessibleclean and safe just remember you are on island timeHost:
rob gave us good advice on local restaurants and venues and was a great hosthost has great communicationthey really capture easy florida living on the property and the host rob was very hospitable and welcomingRead more reviewsLocation:
great location quiet yet close to everythinggreat locationthe location was greatin a great locationthe apartment is cute and relaxing conveniently located while still quiet
10. Charming waterfront property directly on canal
Newly renovated, this property is located just off a canal. It offers a large open-plan main area that includes a living room, dining space and a kitchen. There are two bedrooms, but seven guests can be accommodated thanks to a bunk bed in the guest room.
A balcony is available and guests have access to the dock that’s right in front of the house. Pets are welcome, but guests are required to clean up after their furbabies.
Islamorada, Florida, United States
49.15 km (30.6 mi) from Everglades National ParkAccommodates: 7
Top guest reviews
Cleanliness:
wonderful house updated clean on a nice canalRead more reviewsHost:
tim was very responsive
Spend a relaxed break in Islamorada
A Florida Keys vacation promises loads of fun, and Islamorada is an excellent pick for a laidback break. If you want to travel with your pets, then you’ll need a rental that’s comfortable for them too. Our list of pet-friendly Airbnbs in Islamorada, Florida, contains fantastic options so you can find the right one for your needs.
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