Some info has been automatically translated. Show original language

House vacation rentals in Islamorada

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Islamorada house rentals

House rentals with a pool

Top guest favorite
A serene pool area features a heated swimming pool surrounded by palm trees. A small table with an umbrella provides shade, while lounge chairs invite relaxation. The water view is visible beyond the pool, enhancing the tranquil outdoor setting.
Home in Marathon
5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars5 months ago
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.
Guest favorite
A private pool is framed by a spacious deck, offering views of the calm canal water. Lounge chairs are positioned nearby, while a barbecue grill is situated to one side. Lush greenery and palm trees enhance the serene outdoor atmosphere.
Home in Marathon
4.89 out of 5 average rating, 75 reviews

Dream Vacation KCB Marathon with private pool !

AlexsisRating, 5 stars1 week ago
Alfonso, place was great to stay! beautiful view, my son was able to give a manatee water from the dock. we saw tarpon, snappers, needle fish and much more from the deck. Friendly neighbors! very peaceful surroundings. Alfonso, was very responsive and polite . Worth the price, my family loved it!
Superhost
Home in Key Largo
4.86 out of 5 average rating, 100 reviews

Cary’s Oceanside

KrissieRating, 5 stars4 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
A tropical pool area is surrounded by palm trees and lush landscaping. The crystal-clear water sparkles under the sun, while a built-in spa offers a relaxing retreat. The spacious deck features both shaded and sunny spots, creating a serene space for leisure.
Home in Marathon
4.93 out of 5 average rating, 29 reviews

Serenity Bay Estate-FL Keys Best Kept Secret! Beau

JerrieRating, 5 stars6 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
A heated swimming pool is featured in a wooden deck area, surrounded by tropical palm trees. Lounge chairs are positioned for relaxation, while the exterior of the two-story home includes expansive glass doors that provide a view of the inviting pool and canal.
Home in Islamorada
4.86 out of 5 average rating, 7 reviews

Venetian Tropics private heated pool at 82 degrees

JessicaRating, 5 stars8 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.
Guest favorite
A private pool is positioned in a landscaped yard, accompanied by an umbrella for shade. The setting features views of a canal, with boats docked nearby, complemented by tropical plants and a light-colored exterior of the duplex.
Home in Key Colony Beach
5 out of 5 average rating, 83 reviews

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

KarenRating, 5 stars1 month 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
A private heat-optional pool is set in a spacious yard with a patio, surrounded by lounge chairs. The home features large glass doors that provide views of the canal and the lush landscaping nearby.
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 stars32 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 month 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!

House rentals with free parking

Top guest favorite
An aerial view captures the duplex home situated near a canal with multiple boats docked along the water. The vibrant homes are seen in a tangle of greens and blues, with sandy pathways and lush landscaping complementing the serene coastal environment.
Home in Marathon
5 out of 5 average rating, 17 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars1 day ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Guest favorite
A modern interior showcases a spacious living area with a sectional sofa adorned with decorative cushions. Adjacent, a bright kitchen is visible, alongside a dining table. A cozy bedroom features a bed with plush linens. Outdoor seating is arranged on a covered patio, surrounded by greenery.
Home in Marathon
4.9 out of 5 average rating, 162 reviews

Waterfront Cozy Modern Retreat w/Deep Canal

TheresaRating, 5 stars2 days ago
Christy was the best host! She was always available for quick questions and gave us great information as well. Her home was gorgeous! Beautifully decorated, flooring was luxurious and the space was perfect for the 2 us and our boat. The back porch was comfortable and the gas grill was a work of art! The boat ramp was a 1 mile away, Publix and Winn Dixie right around the corner and many restaurants all around made the location perfect for us. We had such a great stay and would definitely stay here again!! Thank You Christy for sharing your beautiful home with us!
Guest favorite
A two-story duplex is set amidst palm trees, featuring a blue exterior and multiple balconies. A vehicle is parked in the driveway, with a pathway leading towards the entrance, surrounded by landscaped areas that include gravel and greenery.
Home in Key Largo
4.91 out of 5 average rating, 169 reviews

Blue House Marine in Key Largo

AprilRating, 5 stars1 week ago
Beautiful home. Close to everything. Easy check in. Very responsive hosts. We would definitely book here again.
Guest favorite
An aerial view captures the Snapper House situated alongside expansive canals, with direct access to the water. A red marker highlights the property’s location. Surrounding homes and palm trees create a vibrant neighborhood environment, reflecting the essence of coastal living.
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 month 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.
Superhost
A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.
Home in Cudjoe Key
4.83 out of 5 average rating, 264 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

AlexRating, 5 stars3 weeks ago
The house was exactly as pictured and in a very peaceful community. The beds were comfortable, as was the couch (two of our group opted to sleep on the couch itself instead of pulling out the sleeper sofa, and said it was pretty comfy!). Several of our group enjoyed using the bikes at night, and while we didn’t use the kayaks, it’s nice they were available. We didn’t get to do everything we hoped to do on our trip to Keys, but we plan to stay here again someday when we come back!
Superhost
An aerial view of a spacious pool surrounded by lush greenery and palm trees. The pool features a unique, winding shape, with several lounge chairs arranged around the perimeter and shaded spots provided by umbrellas.
Home in Key Largo
4.92 out of 5 average rating, 132 reviews

Mariners Club Resort, Best in the Upper Keys

AaronRating, 5 stars1 month ago
7 of us got together to celebrate our brother getting married, and it was super relaxing and chill. A lot of oceanic adventures and things to do in the area, plus the resort amenities was nice bonuses to enjoy, which is all exactly what he wanted. We had a swell time, and everyone was friendly in the area too. Host was communicative and everything went smoothly for us. Thank you!
Guest favorite
A tranquil sunset casts warm hues over the water, with gentle ripples reflecting the orange and yellow tones. Silhouetted trees and distant mangroves create a natural backdrop, contributing to the serene ambiance of the scene.
Home in Key Largo
4.89 out of 5 average rating, 95 reviews

Little Peace of Haven

breeRating, 5 stars1 week ago
very spacious super clean perfect for a family and hist was very easy to get a hold of i would highly recommend
Guest favorite
A serene view overlooks the water at sunrise, with soft pastels reflecting on the surface. A white patio table and chairs are positioned under the covered porch, inviting relaxation. The horizon features gentle clouds and distant islands, creating a peaceful atmosphere.
Home in Cudjoe Key
4.91 out of 5 average rating, 34 reviews

Rise And Shine On The Water

FlorianRating, 5 stars2 weeks ago
There were five of us in the house and we felt immediately comfortable. Everything was super clean. The location right on the water was overwhelming as expected. Everything that is needed was there. The kitchen and terrace were very large and the mattresses were very comfortable. Key West is about 30 minutes away. Check-in and check-out as well as contact were completely unproblematic. We will be back!

Weekly house rentals

Guest favorite
A tranquil canal scene is depicted, lined with palm trees and private docks. Water reflects the clear blue sky, creating a serene atmosphere. Boats are moored along the canal, showcasing direct access to Gulf and Ocean waters.
Home in Marathon
5 out of 5 average rating, 40 reviews

Yellowtail Getaway with Boat Dock and Pool 2

HopeRating, 5 stars2 months 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.
Top guest favorite
A serene waterfront scene captures colorful sunset hues reflecting off calm waters. Palm trees sway gently in the breeze, while boats are moored along the canal. The peaceful atmosphere of the neighborhood is evident in the backdrop of charming docks and nearby structures.
Home in Marathon
4.91 out of 5 average rating, 69 reviews

Blue Ocean Bungalow Spring discounts available

HixRating, 5 stars2 months 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
The image captures a sandy beach scene with clear turquoise waters. Sunbathers and beachgoers are seen enjoying the sun on the shore, while lush palm trees line the beach. A beachfront villa is visible in the background, enhancing the coastal setting.
Home in Marathon
4.91 out of 5 average rating, 178 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars2 weeks ago
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!
Guest favorite
A bright exterior view showcases a charming home perched on the canal's edge. Lush greenery frames the property, while a private dock extends into the water. Sunlight reflects off the calm water, and a blue sky dotted with fluffy clouds enhances the tranquil setting.
Home in Marathon
4.96 out of 5 average rating, 70 reviews

Private 174ft Dock, Boat Launch, Sombrero Beach

JesseRating, 5 stars2 weeks ago
The place was very beautiful! Excellent view of the water and manatees. Great experience.
Top guest favorite
A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.
Home in Key Colony Beach
4.98 out of 5 average rating, 104 reviews

Waterfront House with 37 ft Dock & Cabana Club

CatherineRating, 5 stars1 month ago
Jorge was an excellent host! The home is beautiful, right on the canal. It is very well stocked with thoughtful amenities. We particularly appreciated the paddle board/kayaks, beach chairs/umbrella, and well-supplier kitchen. We would recommend his home to anyone visiting the keys!
Superhost
A pair of outdoor chairs is positioned on a balcony, overlooking a vibrant canal. Palm trees and neighboring homes line the waterway, while a bright sky filled with fluffy clouds enhances the serene waterfront view.
Home in Cudjoe Key
4.87 out of 5 average rating, 104 reviews

Island Oasis ~ YOUR Paradise Awaits!

AbbyRating, 5 stars1 month ago
Bonnie was a nice, responsive host and even brought us additional kayaks to use. We had a great stay!
Guest favorite
A private backyard features a newly renovated pool and spa combo, surrounded by a concrete patio. The stilted house above is complemented by a spacious screened-in porch with teal seating. Lush greenery enhances the tropical ambiance of the outdoor space.
Home in Marathon
4.97 out of 5 average rating, 35 reviews

Marathon 3BR Canal Home w Pool Spa Combo 55' Dock

MattRating, 5 stars1 month ago
Great peaceful place to stay. We saw manatees, tarpon and many other species in the canal. Also had some short visits from different types of lizards and iguanas. The pool and hot tub were amazing everyone in our group enjoyed them. The dock was a great place to keep our rental boat. I would 100% come back.
Guest favorite
A vibrant exterior view of the Purple Pelican Inn is presented, showcasing a colorful building with a light blue facade and purple accents. A picnic table is located beneath a large umbrella, surrounded by lush greenery and blooming purple flowers. Gravel paths lead toward the entrance.
Home in Key Largo
4.9 out of 5 average rating, 87 reviews

The Purple Pelican Inn/Private Hot Tub

DanaRating, 5 stars1 week ago
Our stay was really nice, we enjoyed riding our bikes around the camp ground at night to cool off and we felt very safe. It was an extremely charming location and allowed us to go to other places where we had excursions planned. It was a nice clean space to come back to after our long days of exploring. (:

Quick stats about house rentals in Islamorada

  • Total rentals

    330 properties

  • Nightly prices starting at

    $100 before taxes and fees

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    310 properties are a good fit for families

  • Pet-friendly rentals

    160 properties allow pets

  • Rentals with a pool

    210 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. House rentals