
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.

Sea Ray Cove; Pool, 75’ Dock and steps to Beach
2025 - New concrete dock, fenders & fish filet table. This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Condo in the Keys, Peaceful ocean view retreat!
Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
***9/2/25 to mid-November, building , elevator and balcony improvements will take place and our rates are heavily discounted for the inconvenience. Balcony access may be affected. No work on weekends , holidays or Thanksgiving week. All amenities are open.*** Stay at our tropical hideaway rated one of the “Coolest Airbnb’s in the Keys” by Trips to Discover! Our romantic condominium (sleeps 4) is located at the gated Ocean Pointe resort with full amenities- pool, beach, marina, tennis, cafe

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.

Exquisite Oceanfront Paradise - Key Colony Beach
Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

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.

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.

Luxury Heated Pool/Jacuzzi, Games & Nice Backyard.
✨Bring the whole family to this great located house with a nice pool with spa, combo game table and lots of room for fun, and enjoy the beach, restaurants and entertainments around the area. ✨5BRs with smart TVs and comfortable mattresses and pillows. 3BR upstairs/2BR downstairs. ✨3 bathrooms, 1BR downstairs/2BR upstairs. ✨2 kitchens fully equipped with everything you may need. ✨Nice and quite neighborhood. ✨Sunsets are amazing at The Florida Keys. ✨Guest are always our priority.

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.

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

Pristine pool front home w/ocean views Anglers 148

Tiny Home on Waterfront | Bay Views | Deck | Pool

Conch Cottage at Hawks Cay - Chic Tropical Retreat

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

CASA AZUL Golf Cart, Kayaks, Pools, Beach, 2 Kings

Waterfront House with 37 ft Dock & Cabana Club

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

Tiki Time
Condo rentals with a pool

1BR - Key Largo Sun & Sand Hideaway

Reel Large END Unit in Ocean Point Suites

500 Burton Drive Tavernier, Key Largo

Serenity In The Sun

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Ocean Views at Ocean Pointe

Ocean views at “Sangria Sunrise” 10% off Charters

Studio with Balcony, Kitchen, Open Living Space
Other vacation rentals with a pool

Islamorada bungalow 2 bed & pool

Islamorada house with best location. Lic # 24-0055

When Paradise is Key: Tropical Oceanfront Condo

Beach House, Private Pool & Dock, Gulf Sunset view

New! 4-Story Villa w/ Rooftop & 3 Private Suites

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

Panoramic Oceanside Luxury, Dockage & Gameroom

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis
Quick stats about vacation rentals with a pool in Islamorada
Total vacation rentals
Explore 630 vacation rentals in Islamorada
Nightly prices starting at
Islamorada vacation rentals start at R1,214 ZAR per night before taxes and fees
Verified guest reviews
Over 3,880 verified reviews to help you choose
Family-friendly vacation rentals
440 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
- Coral Castle
- Cannon Beach
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Conch Key
- Theater of the Sea
- Everglades Alligator Farm
- Far Beach
- Monkey Jungle
- Sea Oats Beach
- Horseshoe Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
- Keys' Meads
- Sandspur Beach
- Long Beach
- Schnebly Redland's Winery & Brewery