
Holiday rentals with a pool in Islamorada
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Islamorada
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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.

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

1BR - Key Largo Sun & Sand Hideaway
Welcome to Key Largo Sun & Sand Hideaway, where relaxation awaits in the beautiful Florida Keys. Our fully equipped one-bed, one-bath suite is the ideal destination for your next vacation. Nestled within an oceanfront resort, you'll enjoy access to a private beach, marina and other amenities. Indulge in a serene coastal experience just minutes away from restaurants, shopping, and other exciting water activities. Unwind, rejuvenate, and create unforgettable memories in this tropical paradise.

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

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.

Toes in the Sand - 2 Bedroom Condo Sleeps 4
2-bedrooms, 2 full baths located on the 4th floor with ocean views. This condo has a beach, viewing pier, rentable boat slips, & boat trailer storage, café and a very large heated pool with a bar and gated entry with 24 hour security! Perfectly located between Key Largo and Islamorada, close to Pennekamp State Park, Harry Harris State Park, popular restaurants on the water, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

Blue Haven Key Largo | Ocean Pointe 1315
Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!

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!

2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

Kawama N2 Relaxing Lagoon View free bikes & kayaks
Relax and enjoy our family friendly 3 bedroom/3 bathroom Villa Lago in Key Largo! Salt water swimming lagoon, Pools, the Ocean, fishing pier, Marina, Tennis, Bikes, fire pit and playground. Enjoy resort like amenities in the comfort of a home. This beautifully decorated villa sleeps 8 and is conveniently located in a very central location in Key Largo. Close to some great restaurants, diving, fishing, boat tours, State Park. Kawama is fun for all ages.

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

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

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

Blue House Marine in Key Largo

The Paradise 2

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Key Largo Waterfront: Tiki, Dock, Kayak & Pool

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes

Mariners Club Resort, Best in the Upper Keys

Waterfront House with 37 ft Dock & Cabana Club
Apartment rentals with a pool

Reel Large END Unit in Ocean Point Suites

Your Happy Place - Oceanfront

Enjoy sunsets & sunrise in your home away home.

Condo in Tavernier

Tequila Sunrise

Ocean views at “Sangria Sunrise” 10% off Charters

Beachside Unit 33-Private Tropical Beach Plus Pool

Tropical Getaway
Other holiday rentals with a pool

3 EnSuite Bedrooms,FREE boat dockage Sept-Oct only

Islamorada house with best location. Lic # 24-0055

Twilight #32 Key Largo 4BR Villa | Pool,

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Oceanfront 3‑Stories of Bliss • Dockage & Gameroom

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

Bayview Beautiful townhouse in Islamorada, FL KEYS

Bohemian Beach Bungalow
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 311 | € 364 | € 377 | € 311 | € 421 | € 303 | € 355 | € 309 | € 306 | € 264 | € 279 | € 304 |
| 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 |
Quick stats about holiday rentals with a pool in Islamorada

Total holiday rentals
Explore 620 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at € 59 per night before taxes and fees

Verified guest reviews
Over 4,040 verified reviews to help you choose

Family-friendly holiday rentals
420 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 320 rentals that welcome pets

Rentals with dedicated workspaces
390 properties have a dedicated workspace

Wifi availability
620 of Islamorada holiday rentals include wifi 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
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Coral Castle
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Everglades Alligator Farm
- Long Beach
- Conch Key
- Bahia Honda State Park
- Theater of the Sea
- Monkey Jungle
- Homestead-Miami Speedway
- Key Largo Kampground And Marina
- Calusa Campground
- Sunset Park
- The Turtle Hospital
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Founder's Park
- Seven Mile Bridge




