
Vacation rentals with a pool in Islamorada
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Islamorada

Total vacation rentals
Explore 640 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at R1,158 ZAR per night before taxes and fees

Verified guest reviews
Over 4,090 verified reviews to help you choose

Family-friendly vacation rentals
420 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 330 rentals that welcome pets

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wi-Fi availability
640 of Islamorada vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Islamorada rentals

4.7 Average rating
Islamorada stays receive an average rating of 4.7 out of 5 from guests
Top-rated rentals with a pool in Islamorada
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Islamorada bungalow 2 bed & pool
Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

Charming 2BR cottage in prime keys location w/pool
Your slice of Islamorada awaits at Key Lime Cottage! Step inside this 2-bedroom retreat and you’ll instantly feel at home. Tucked in a quiet neighborhood yet right in the heart of the Florida Keys, it’s the perfect blend of relaxation and convenience. Enjoy a full kitchen, access to a beautiful pool shared with just six homes, outdoor seating with a grill and fire pit and paddle boards. Whether you’re here to unwind, explore, or fish, everything you need for a perfect Keys getaway is right here.

Toes in the Sand - 2 Bedroom Condo Sleeps 4
Two bedrooms and two full bathrooms on the 4th floor with ocean views. Amenities include a huge heated pool and hot tub with a bar, a beach cafe serving food and drinks, a private Key's beach, viewing pier, rentable boat slips & boat trailer storage, tennis, pickleball courts, basketball, children's swings, and BBQ areas, and gated entry with 24-hour security! Just remember that you're on "Island Time," mon, relax and enjoy! Perfectly located between Key Largo and Islamorada, close to Penneka

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Best View Ocean Pointe Pool Beach King Bed, Gated
***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Your Happy Place - Oceanfront
Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

Waterfront Studio 2| Couples Oasis | Kayaks | Pool
Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Great key Largo home with water front and pool
we have a dog clean fee , always ask the before booking Fantastic canal front home located in Key Largo. Bring your own boat and enjoy it all! The home is minutes away from Gilbert resort, best seafood in the world at any number of local restaurants, Souvenir stores and the best fishing and diving spots. The home has 2 bedrooms and 2 bathrooms, fully furnished, spacious living room with large TV, Full kitchen with all appliances and amenities and a beautiful deck

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views
Popular amenities for Islamorada rentals with a pool
House rentals with a pool

Beach House in Marathon with Amazing Backyard!

Blue House Marine in Key Largo

3/2 Home w Dock, lagoon, kayaks!

4BR 3B, Heated Pool & Spa, 60' Dock

Marathon one-level home on the Marina - with slip!

The Villa by the Bay Unit 2 Private Pool/Boat Dock

SAY'S BY THE SEA

Ocean view, seaside paradise with golf cart.
Condo rentals with a pool

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Ocean Views at Ocean Pointe

Ocean Shores Villa 2 with pool and boat slip

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

Ocean views at “Sangria Sunrise” 10% off Charters

Turtle Nest 1 Private beach,Pool, 2bed 2bath

Beachside Unit 33-Private Tropical Beach Plus Pool
Other vacation rentals with a pool

Key Largo's Best Kept Secret!

Luxury condo with boat slip overlooking the bay

Oceanfront mermaid house pool and dock

Waterfront Key Largo Home - Tropical Paradise

Castillo Del Mar- Ocean access from your backyard

Panoramic Ocean Views, Ocean Pointe Condo

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

Condo in Tavernier
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R6,103 ZAR | R7,145 ZAR | R7,410 ZAR | R6,103 ZAR | R8,270 ZAR | R5,954 ZAR | R6,980 ZAR | R6,070 ZAR | R6,004 ZAR | R5,194 ZAR | R5,475 ZAR | R5,971 ZAR |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
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- Rentals with pools Monroe County
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Long Beach
- Coral Castle
- Homestead-Miami Speedway
- Schnebly Redland's Winery & Brewery
- Sea Oats Beach
- Bahia Honda State Park
- Theater of the Sea
- Everglades Alligator Farm
- Conch Key
- Calusa Campground
- Sunset Park
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Monkey Jungle
- Robbies Marina Of Islamorada
- Dolphin Research Center
- Founder's Park
- Florida Keys Aquarium Encounters
- The Turtle Hospital




