
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 670 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at R 1,137 ZAR per night before taxes and fees

Verified guest reviews
Over 4,630 verified reviews to help you choose

Family-friendly vacation rentals
400 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
4.95 out of 5 average rating, 106 reviews
Sunrise Escape - Ocean Front Villa - Sleeps 10
Wake up to the sunrise over the ocean and unwind with sunset views from your private jetty. This marina-front, ocean-view townhouse in Kawama Yacht Club puts you steps from kayaking, snorkeling, and the best of the Keys. Spacious, stylish, and designed for unforgettable family and friend getaways. Breathtaking sunrises from one of two private terraces, coffee in hand, overlooking the marina and the Atlantic Ocean. Located in an exclusive, quiet section of Kawama Yacht Club, this beautifully po
4.87 out of 5 average rating, 181 reviews
Tiny Home on Waterfront | Bay Views | Deck | Pool
Down by the waters of Manatee Bay, you’ll find this idyllic tiny home for 6. With a full kitchen, three comfy beds,and access to a community pool, this is a prime location to enjoy the best of Key Largo. Sit on the deck and dip your toes in the water or explore the bay using the available kayaks and paddle boards. 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!
4.91 out of 5 average rating, 207 reviews
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.
4.97 out of 5 average rating, 234 reviews
Oceanfront Lookout Point w/two Kayaks & Deck
Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.
4.96 out of 5 average rating, 213 reviews
Largo Getaway: 3 King Suites + In-Law Space
🔑 Managed by KEYLARGOTRAVELS See our profile for all listings. VIRTUAL TOUR: YouTube @Keylargotravels, go to Shorts it is called Mariners 🛏 SLEEPING Bedroom 1 – First Floor In-Law Suite: King bed, en-suite full bathroom with shower, plus a full-size sleeper sofa in the living area Bedroom 2 – Third Floor Master: King bed, en-suite full bathroom, plus a twin floor mattress available if needed Bedroom 3 – Third Floor Guest Suite: King bed plus twin bunk beds, en-suite full bathroom
4.93 out of 5 average rating, 100 reviews
My Little Oasis3 Waterfront Retreat Key Largo
Best of the Best, very exclusive, located on the oceanfront with a million dollar view, this tiny house is on a higher level than the others, is comfortable and cozy. It is ideal for a couple who want to escape. The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property. 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
4.99 out of 5 average rating, 113 reviews
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.
4.99 out of 5 average rating, 225 reviews
Oceanfront Resort W/Indoor Pickleball - Speakeasy!
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Key Largo's most upscale oceanfront community. The area has the distinction of being Key Largo's newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simple desire the very best in luxury accommodations. Unique amenities include a Speakeasy Themed Rec. Area.
4.82 out of 5 average rating, 126 reviews
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.
5.0 out of 5 average rating, 120 reviews
2BR Island Cottage | Pool • Grill • Near Robbie’s
SEPTEMBER & OCTOBER SPECIAL — SAVE 30%! 🍋 Escape to Key Lime Cottage, a charming 2BR retreat in the heart of the Florida Keys. Enjoy a full kitchen, beautiful pool shared with just 6 neighboring cottages, outdoor seating, grill & fire pit, and paddle boards. Close to Robbie’s Marina and perfectly located for fishing, dining, exploring or simply relaxing. Limited fall dates remain at this special rate — book your Keys getaway while the deal lasts!
4.96 out of 5 average rating, 152 reviews
Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
Stylish, fully remodeled end-unit condo in Ocean Pointe — steps to the beach! ☞ Resort access (pool + hot tub) ☞ Private beach access w/ sun loungers ☞ Fully equipped + stocked kitchen ☞ Smart TVs + bluetooth sound system ☞ Workspace + 350 Mbps wifi ☞ Tennis/pickleball courts ☞ BBQ grill + picnic tables ☞ Parking lot (2 cars max) 5 mins → DT Tavernier (cafes, dining, shopping) 15 mins → John Pennekamp Coral Reef State Park
5.0 out of 5 average rating, 103 reviewsPopular amenities for Islamorada rentals with a pool
House rentals with a pool

Florida Keys Resort-Style Home w/ Pool & Dock 5/3
4.95 out of 5 average rating, 152 reviews
The Paradise 2
4.9 out of 5 average rating, 174 reviews
Waterview from three sides, Cabana Club, 30' Docks
4.85 out of 5 average rating, 189 reviews
Mariners 212 Great Location with Marina Views
4.93 out of 5 average rating, 123 reviews
El Encanto | Private pool & tropical tiki
4.96 out of 5 average rating, 24 reviews
Islamorada Bungalow #5
4.81 out of 5 average rating, 42 reviews
OceanView 2/2.5 w Beach Pool & Marina Islamorada
5.0 out of 5 average rating, 22 reviews
Marathon Oceanfront 4BR Private Pool 60’ Boat Dock
5.0 out of 5 average rating, 6 reviewsCondo rentals with a pool

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
4.96 out of 5 average rating, 252 reviews
Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
4.94 out of 5 average rating, 160 reviews
Your Happy Place - Oceanfront
4.95 out of 5 average rating, 152 reviews
Amazing Ocean Front Views Key Colony Beach
4.97 out of 5 average rating, 286 reviews
Gorgeous lagoon-front 2BR Townhouse with 2 pools
4.91 out of 5 average rating, 171 reviews
SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
4.9 out of 5 average rating, 338 reviews
Mad Mahi | Housekeeping + Waterfront + Marina View
4.9 out of 5 average rating, 156 reviews
BEAUTIFULLY DESIGNED OCEANFRONT CONDO
4.93 out of 5 average rating, 172 reviewsOther vacation rentals with a pool

When Paradise is Key: Tropical Oceanfront Condo
4.88 out of 5 average rating, 102 reviews
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
4.96 out of 5 average rating, 79 reviews
Fishing Getaway | Dock, Pool & Sunrise
5.0 out of 5 average rating, 14 reviews
NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom
4.97 out of 5 average rating, 35 reviews
The Lighthouse | Ocean + Pool Views, Gameroom
5.0 out of 5 average rating, 3 reviews
4-Bedroom Coastal Retreat *Special Fall Rates*
5.0 out of 5 average rating, 11 reviews
Condo in Tavernier
4.96 out of 5 average rating, 55 reviews
Tropical Keys Retreat | Pool | Hot Tub | Cinema
5.0 out of 5 average rating, 81 reviewsWhen is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R 6,156 ZAR | R 7,439 ZAR | R 7,732 ZAR | R 6,887 ZAR | R 5,896 ZAR | R 5,441 ZAR | R 6,855 ZAR | R 5,961 ZAR | R 5,896 ZAR | R 5,100 ZAR | R 5,376 ZAR | R 5,864 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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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Homestead-Miami Speedway
- Schnebly Redland's Winery & Brewery
- Coral Castle
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Everglades Alligator Farm
- Key Largo Kampground And Marina
- Theater of the Sea
- Ernest F. Coe Visitor Center
- Florida Keys Aquarium Encounters
- Harry Harris Beach and Park
- Dolphin Research Center
- Monkey Jungle
- Founder's Park
- History Of Diving Museum
- Homestead Bayfront Park
- Calusa Campground
- Conch Key





