Islamorada is a charming village that covers six of the Florida Keys, a chain of islands that lines the southernmost edge of Florida. It is best known for its white sandy beaches and gorgeous ocean views. It is also the Sport-Fishing Capital of the World. Depending on the time of year, the waters are brimming with kingfish, sailfish, bonefish, tuna, marlin, and mahi-mahi. Islamorada is also home to some great accommodations, with many of them being beachfront properties ideal for seaside lazing. Some of these even come with a private pool, so you can go for a swim whenever you wish. To help you choose your ideal accommodation, here’s our pick of the best vacation rentals with private pool in Islamorada, Florida.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to private pool. The image galleries get refreshed with the latest updates regularly. They were last updated on April 12, 2024.
1. Lovely cottage with an expansive deck (from USD 415)
With a spacious deck and docking area for a boat, this cottage is designed for guests who love the outdoors. The swimming pool is kept pristine and has sun loungers by its side, so you can top up your tan. The second-floor has a terrace where you can enjoy your meals while taking in the canal and pool views.
Upstairs, there’s also a fully equipped kitchen and a plush living area with a TV. The four bedrooms can fit a total of eight guests, and the three bathrooms provide enough room for everyone to keep fresh and clean.
Top guest reviews
Amenities & Room:
recently remodeled with coastal decor great furnishings and a pool which was invaluable with the kids( ceiling fans throughout house and maintenance on the wood deck) beach privilege on bayside was enjoyableHost:
very pet friendly home with fenced in yardRead more reviewsLocation:
quick walk to fresh seafood market
2. Gorgeous oceanfront house with five bedrooms (from USD 1400)
This sleek and stylish oceanfront house can sleep 10 people in its 5 bedrooms. Each room boasts incredible views of the ocean. When not at the private beach, which is steps away from the property, cool off in a private pool. It can also be heated for extra relaxation.
When you aren’t going for a swim, you can even sit back and sunbathe poolside on the comfy lounge chairs. Active guests can fish or kayak from the private observation dock, or just enjoy the views. Three kayaks and two paddle boards are available in the house.
Top guest reviews
Cleanliness:
light bright and clean it has everything you need for a great beach vacationHost:
the owner was gracious and helpful with all of our questionsowners were easy to work withchausey is an awesome hosteverything was as expected from the listing and the host was helpful and easy to work withRead more reviewsLocation:
a wonderful location to rest relax and recoverwe loved the house and locationthe location the layout both inside and out and the access to fun activities were all huge benefitsexcellent location with magnificent views
3. Southern Diversion (from USD 1499)
With space for up to 16 guests, this 5-bedroom cabin is perfect for family gatherings or friends’ reunion. After a fun-filled day at the private beach with a dock and tiki hut, enjoy an afternoon cookout on the patio, complete with a gas grill and a dining area.
You can also hop into the outdoor pool and enjoy unobstructed views of the sea while swimming. The cabin also has a fully equipped kitchen, flat-screen TVs in all the rooms, and multiple balconies overlooking the sea.
Top guest reviews
Amenities & Room:
towels - everything you will need for outsideOur family came here to celebrate our parents 40th wedding anniversary and it was amazingThe house had plenty of room for all our extended family including a bunch of young kiddosThe bunk room was perfect for all the cousins to sleep inThe property was just beautiful - from the tree lined drive up to the front of the home to the postcard-like views of the ocean out backCleanliness:
The house was exactly as describedThe pool was lovely as were the views from this spacious propertyThe four bathrooms were greatthe house is very well appointed clean large and roomyWe were able to accommodate approximately fifty guests caterers a bandHost:
The caretaker John was very helpfulThey could use some more pool towels Owner not the easiest to work withthe groundskeeper was super-helpful and available whenever we needed himwell-kept responsive owner to questions and requests and a great conciergeI P experience and was very helpful in explaining the dock lift channel to bring our boat inRead more reviewsLocation:
Conveniently located to good restaurantsThe house is in the perfect location being close to restaurants and activitiesThe dock was a perfect This area of the island has plenty of restaurants activities bars and shoppingThis property is directly across the street from an amazing spaVery close to great dining and convenient to shopping and the tackle shop We will definitely return for another stay but longer
4. Happy Tarpon (from USD 500)
Happy Tarpon is an inviting and spacious house, with a large yard and a boat dock. Active guests can indulge in boating, fishing, canoeing, and other outdoor activities nearby. The house also has an outdoor swimming pool, which is easily accessible from the living area and kitchen. The pool is heated, so you can enjoy a swim at any time of the year.
For those less athletically inclined, there’s a sunning deck for relaxing and cable TVs and wireless internet access to keep you entertained. Inside, you’ll also find three bedrooms and three bathrooms, allowing up to six guests to stay here. The kitchen is fully equipped for cooking and baking needs.
5. Perfect Escape (from USD 572)
If you want the perfect escape from the urban grind, the aptly named Perfect Escape residence is your ideal spot. With four bedrooms and four bathrooms, up to eight guests can sleep soundly here.
A large cabana, sun loungers, and a living room are all perfect spots where you can spend quality time with your family. You can splash around with your loved ones in the private pool, which can also be heated for an extra cost of 250 USD per week. For more water fun, a boat is also available for rent on site — just be sure to contact the owners in advance for arrangements.
Top guest reviews
Amenities & Room:
the balcony had amazing views of the pool and waterexcellent location nice pool gated yard and plenty of dock space that has recently been redonefantastic place for family and friends with a poolCleanliness:
upon arrival everything was super cleanone dish rag and one hand towel per bathroom was inconvenient since clean ones are needed dailythe house was clean and there was ample parking for three cars and a boat trailerthe house was spotless everything works well and arlene was a terrific and extremely accommodating hostHost:
everyone was very friendlythe owner was so easy to work witharlene was very responsive to questions prior to and throughout our stayarlene was super responsive to any questions and or needsthe set up is perfect for multiple families and the owner is very responsive with any questionsRead more reviewsLocation:
great house to stay and perfect location just minutes from the atlanticgreat location and convenient to have dock for boatgreat location with a boat rental company very closethe house and the location couldn’t be better
6. The Russell Estate (from USD 745)
This holiday retreat sits within a premium property that faces the ocean and boasts plenty of white sand. The outdoor pool with sun loungers is the best spot to enjoy unobstructed view of this scenery. The pool itself is a relaxing spot to take a dip during the hotter days.
Inside the home, you’ll find a wide selection of modern comforts, including a full kitchen, TVs, and even a small workspace, to name a few. The three bedrooms are more than enough for six guests to have a good night’s sleep.
Top guest reviews
Cleanliness:
the house is very cozy comfortable and cleanHost:
denira and alex were amazing hoststhanks for being a host and creating lifetime memories for our familycheck in was easy and the owner provided some much appreciated flexibility on check outthe long dock was a great lookout for all kinds of fishhe was responsive to texts and very helpfulRead more reviewsLocation:
location was so perfect and convenientgood location and great hoststhe perfect place to spend time on the best florida keythis is a wonderful place to stay and isla morada is beautifulif you're looking to relax this is the place to be
7. Bright and airy house for eight (from USD 449)
This eight-person house has all the amenities you’d want from a home away from home. Each of the property’s three bedrooms has a bathroom, so everyone can sleep well and feel fresh all day. You can spend your time watching TV while relaxing on the plush couch in the living area.
However, it’s the outdoor features that really shine in this property. On one end of the house is a mini putting green, and right beside it is the boat dock. The pool is perfect for the summer months, though you can have it heated during cooler months for an extra charge of 15 USD a day.
Top guest reviews
Amenities & Room:
the house is very comfortable and the peekaboo ocean view is fantasticthe pool is great with afternoon shade which was great after a day in the sunCleanliness:
the house was very clean and well maintainedclean fresh and great communication with the ownera++++ minutes from the ocean by boat lots of tarpons in backyard clean spacious quietthe home is stylishly decorated very clean great kitchen and plenty of spaceHost:
the host was extremely quick to respond and help us with whatever we neededwe loved this home in islamorada it is beautifully decorated and very clean the host provided most essentialsRead more reviewsLocation:
house is in excellent condition location is fairly privategreat location on and off the waterthe location of the house is perfect for getting to various local restaurants and marinasbeautiful home at a great location area was secluded and quietwe had a great week at jaime & mike’s place super convenient to the oceanside bayside and local marina
Superhost
8. Charming house with a large covered terrace (from USD 485)
Decked out in pastel blue and white hues, the cottage is reminiscent of the island’s pristine shores. It has a washer and dryer, so there’s no need to worry about your laundry. There’s also a well-equipped kitchen for self-catering, and you can enjoy your meals in the outdoor dining area.
The outdoor pool is the perfect spot to cool off on a warm day, while the large covered terrace upstairs is great for relaxing in the evening as the sun goes down.
Top guest reviews
Cleanliness:
a nice fish cleaning table and fresh water on the dock for easy clean upthe house was just as described and was very clean on arrivalvery clean great location and communicative hostHost:
we highly recommend this home as adriana was an amazing host and the home is well cared forleft the owner just a few tips to make future visits that much betterthe neighborhood was quiet welcoming friendly & safeRead more reviewsLocation:
place is well worth it beautiful home and great locationgreat spot in a great location sweet little private beach within walking distance was icing on the cakethe house and location are hard to beat very nicely decorated and furnisheda great place to vacation
9. Bayside house in the heart of Islamorada (from USD 1125)
This luxurious oceanside retreat is ready to accommodate up to 10 guests, with 5 bedrooms and 4 baths allowing everyone to feel at ease. It comes with mod-cons such as a large-screen TV, two-door fridge, and central air conditioning, perfectly complement the house’s chic interior.
With a full kitchen at your disposal, preparing delicious meals for everyone is a breeze. At the backside of the property, there’s a gorgeous pool area where you will be treated to stunning views of the sea and sun as you take a dip in the swimming pool.
Top guest reviews
Amenities & Room:
the heated pool came in handy as the nights got very cool during our staywe fished watched the manatees and loved the heated poolCleanliness:
the house was very clean and extremely well stocked (kitchen towels extra linens cleaning supplies puzzles)it is so classy and clean and stylisheverything was great the property was very clean and has clearly been renovated recentlythis property is absolutely beautiful clean everything you need and morehouse is tastefully decorated in a clean upscale beachy decor and very comfortable for all ages 1-64Host:
the home owners couldn’t be more courteous and attentive when ever we contacted themshe is extremely responsive and made us feel that she was always a text or call awaythe owners were great and very prompt in respondingthe owners were fantastic to deal with and extremely responsiveour group which was three couples thoroughly enjoyed the updated waterfront home and the owners attention to detailRead more reviewsLocation:
great location walking distance to many great restaurants and storesexcellent property and great locationthe house is conveniently located close to all of the best restaurants and barsvery convenient location bedrooms are spacious and our group of 10 slept very comfortably
10. Well-furnished cottage with unobstructed views of the sea
This beachfront cottage is a treat for families thanks to its modern features, seaside location, and relaxed atmosphere. You can enjoy your morning coffee out while taking in the ocean views and tropical breeze on the upper-floor balcony or the main level patio.
The cottage also has a smart TV, full kitchen, and laundry facilities for your convenience. After a long day, you can take a swim in the outdoor pool overlooking the sea. You can even view the sunset from here, which is a spectacular sight to behold.
Islamorada, Florida, United States
48.44 km (30.1 mi) from Everglades National ParkAccommodates: 4
Top guest reviews
Amenities & Room:
it is a true two bedroom with a king (great memory foam mattress) and queen bedthe pool/hot tub were great for a quick dip before dinneryou are welcome to use the overflow hot tub and the poolCleanliness:
this is a clean and quiet escape for your familywe would do it again and again clean house? yesplenty of space for our family it is clean private and quietHost:
thank you for being gracious and responsive hosts and sharing this home with our familywe did like everything else great wait staff there as wellowners are very responsive and a pleasure to deal with during your staygood owner communication? yesRead more reviewsLocation:
amazing location - one of our new favorite places on the planeta more casual and fun place to eat is lazy days
Enjoy the sun, sea and sand in Islamorada
With gorgeous beaches and a laid-back vibe, Islamorada is a tropical getaway that easily matches the charm and beauty of more well-known coastal cities in Florida, such as Miami and Daytona. Before you pack your flip-flops and shades to head to this stunning destination, be sure to book any of these vacation rentals with private pool in Islamorada, Florida.
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