
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.

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.

Waterfront House with 37 ft Dock & Cabana Club
Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

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.

Oceanfront Sunrise Condo Private Beach Heated Pool
Impeccable condo directly on the ocean with water views. Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #20 offers one king bed, a fully equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys sunset.

Dbl Master |Oceanview |Jacuzzi |Beach |Marina |BBQ
Oceanview condo with tennis courts, pickleball, hot tub, BBQ, marina & private beach. ★ "We absolutely loved the condo - the beds were comfy, and you can see the ocean from the family room. Everything you could possibly need. Responsive hosts and inside was spotless!" ➠ Resort size heated pool + Jacuzzi ➠ Balcony w/ ocean view ➠ Private beach access w/ sun lounger ➠ Fully equipped + stocked kitchen ➠ Double Master Suites ➠ 55” smart TVs w/ cable ➠ Car park (2 cars max) ➠ 250 Mbps WIFI

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.

Ocean Views at Ocean Pointe
Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

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

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!

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
Popular amenities for Islamorada rentals with a pool
House rentals with a pool

Tiny Home on Waterfront | Bay Views | Deck | Pool

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

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Waterfront Home 37.5-ft dock, Cabana Club Included

Mariners 212 Great Location with Marina Views

Tiki Time

Beautiful open plan remodeled home in Key Colony

Private Pool Tropical Oasis - Centrally Located
Condo rentals with a pool

Luxury Top Floor Suite W/ Unobstructed Ocean View

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Your Happy Place - Oceanfront

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Enjoy sunsets & sunrise in your home away home.

🏝 Oceanfront Paradise Awaits You

Beachside Unit 33-Private Tropical Beach Plus Pool

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
Other vacation rentals with a pool

Coastal Oasis #44 Key Largo 4BR Villa | Partial

Islamorada bungalow 2 bed & pool

TheSandbar: Partial Ocean view,Pool,Free Dockage

Seas the Keys Getaway with plunge pool/spa

Condo in Tavernier

P31 - 2 bed, 2 bath with Spectacular Open Water on

Tequila Sunrise

Waterfront Pool Home w/ 30’ Dock, Kayaks & Outdoor
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 322 | € 377 | € 391 | € 322 | € 436 | € 314 | € 368 | € 320 | € 317 | € 274 | € 289 | € 315 |
| 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 € 61 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
- Long Beach
- Coral Castle
- Schnebly Redland's Winery & Brewery
- Sea Oats Beach
- Bahia Honda State Park
- Homestead-Miami Speedway
- Theater of the Sea
- Conch Key
- Everglades Alligator Farm
- Key Largo Kampground And Marina
- Calusa Campground
- Seven Mile Bridge
- Monkey Jungle
- Sunset Park
- Dolphin Research Center
- Founder's Park
- Florida Keys Aquarium Encounters
- Robbies Marina Of Islamorada
- The Turtle Hospital




