
Vacation 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.

Paradise Casa Bayfront sunsets,pool,King bed ,dock
Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

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!

Paradise Palace 3/3 Waterfront Pool Kayak 60' Dock
Close to restaurants and dining, parks, and great views. You’ll love my home because of the peaceful atmosphere, sitting on your own dock watching the boats pass by or friendly manatees swim up. Enjoy swimming in the pool or just relaxing on the patio with a drink in your hand. This home is in a private, gated community and about 10 homes from the bay. A Pontoon boat rental is available(ask for details). Great for families, couples and/or adventurers. Must be age 25 or older to book.

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.

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!

Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.

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!

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Blue House Marine in Key Largo
The house is a Duplex style house for guest it is very quite and private it has 3 bedrooms and two bathrooms kitchen living room and dining area also a walk around balcony its screen in, it has 2 queen style beds and two twin beds. the home has been remodel you have canal views and open ocean viewsfull bathroom by the pool, barbecue area table and chairs for dining plus out door furniture. P.S There is no longer pool heating

Key Largo! Tavernier! Welcome to Paradise!
A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )

Florida Keys Getaway - Slps 4 - Ocean View
Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.

Waterfront Tiny House w Pool, Beach, and Boat Dock
Private community with 2 small beach areas, boat ramp, swimming pool, beach volleyball, children's area with playground, laundry facilities and more. Experience a tastefully decorated, modern 2-bedroom/1-bathroom waterfront tiny house. Relax outdoors with high-top bar seats, lounge chairs, and a grill, perfect for enjoying evenings under the twinkling patio lights.
Popular amenities for Islamorada rentals with a pool
House rentals with a pool

Sea Ray Cove w/ 80' Dock, Pool, Beach & Tiki Hut

Keys to Ohana. Ocean views. Private Pool, Hot Tub

The Paradise 2

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Renovated Anglers Reef 2BR + Sleeper + Ocean Views

Waterfront Home 37.5-ft dock, Cabana Club Included

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

Grand Arenas/ 120'Dock/Mini Golf/HtPool/GameRoom
Condo rentals with a pool

Gorgeous lagoon-front 2BR Townhouse with 2 pools

2BR - Key Largo Sunshine Getaway

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Enjoy sunsets & sunrise in your home away home.

Ocean Views at Ocean Pointe

Luxurious Suite+Open Ocean Views+Pool & Cabana Bar

🏝 Oceanfront Paradise Awaits You
Other vacation rentals with a pool

Sombrero Beach Getaway

Beach House, Private Pool, Dock, Gulf View Sunsets

Panoramic Ocean Views, Ocean Pointe Condo

Casa Blue Flamingo

Ocean Pointe | Pool, Hot Tub, View, Beach, Parking

Saltwater Social ~ Game Room ~ Pool ~ Dock ~ Views

FL Keys Ocean Front Escape

Grouper House: 4 Masters/6 BA, Pool/Dock, BoatRamp
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$77,091 GYD | G$90,253 GYD | G$93,596 GYD | G$77,091 GYD | G$104,460 GYD | G$75,211 GYD | G$88,164 GYD | G$76,673 GYD | G$75,838 GYD | G$65,601 GYD | G$69,152 GYD | G$75,420 GYD |
| 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 vacation rentals with a pool in Islamorada

Total vacation rentals
Explore 620 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at G$14,624 GYD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 320 rentals that welcome pets

Rentals with dedicated workspaces
390 properties have a dedicated workspace

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




