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

Quiet tropical Oasis setting with 1 bed and 1 bath
Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

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.

Charming Key Largo Cottage on the Water w/Kayaks!
Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

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 FRONT WITH AMAZING VIEW AND PRIVATE BEACH
ENJOY THE FABULOUS FLORIDA KEYS IN THIS TOP FLOOR NEWLY REMODELED COZY BEACH CONDO Enjoy this updated 1 bedroom condo on the top floor with amazing ocean views! You will enjoy a full kitchen with stainless steel appliances and granite counter tops equipped for your culinary needs. Your living room has a queen pullout couch and small balcony with a fabulous view! Flat screen TVs are in both the living room and bedroom with a King bed. There is also a washer and dryer in your unit!

The Lighthouse - Beach Houses Key West
If youāre reading this, youāre already one step closer to paradise. Thank you for considering us for your getaway. Our charming Lighthouse Bungalow is a 2-bedroom, 1-bath loft-style retreat located just steps from our private beach. The master bedroom loft, accessed by a spiral staircase, offers a stunning birdās-eye view of the Atlantic Ocean. The nautical-inspired living area opens to an exterior deck overlooking the beachāan ideal spot for peaceful mornings and ocean breezes.

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!

āHave Fun at Hacienda ParaĆsoā Suite 1 | pool |
Welcome to Room 1, the first addition at Hacienda ParaĆso. This suite is conveniently located next to another Airbnb suite, providing flexibility for your stay. It features a private entrance, bathroom, kitchenette, and dining table, ensuring a comfortable and self-contained experience. Enjoy the convenience of hotel-like amenities paired with the added bonus of access to our stunning pool and lush yard, creating a truly relaxing retreat.

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.

The Paradise 2
Relax with the whole family at this peaceful place to stay. Our home is located right by the water. Modern spacious and spotless with private parking, fast Wi-Fi, cold AC plus cozy beds and pillows in every bed. Relax on the waterfront patio chairs, swim in our newly renovated pool, watch the manatees and dolphins swim by and go fishing from our backyard dock anytime. We are sure you will absolutely love our Tiny Home!
Popular amenities for Florida Keys rentals with a pool
House rentals with a pool

Discount Available! Pool 100' Dock, Fun Amenities!

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

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

Cudjoe Key Home with a View

Large Waterfront Home, w/Efficiency, Pool, Kayaks

The Breakaway: Heated Pool with Outdoor Kitchen in

Waterfront Home 37.5-ft dock, Cabana Club Included

Marathon one-level home on the Marina - with slip!
Condo rentals with a pool

SUNNY ISLES GORGEOUS 15A OCEAN FRONT (+hotel fees)

Reel Large END Unit in Ocean Point Suites

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath

2BR - Key Largo Sunshine Getaway

Light, Bright & Nautical Condo at Ocean Pointe

Ocean views at āSangria Sunriseā 10% off Charters

Tropical Getaway

Sugar Cane - Florida Keys tropical retreat
Other holiday rentals with a pool

Waterfront Oasis w/Private Pool-Dockage-Beach

Marathon Keys Escape ⢠Pool ⢠Hot Tub ⢠Near Beach

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

NEW! 4-Story Villa, Private Rooftop, Pool, Marina

Grand Arenas/Hted Pool/120'Dock/MiniGolf/GameRoom

Oceanfront 3-Story Luxury, Dockage, Gameroom

Bohemian Beach Bungalow
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