Holiday rentals with a pool in Key West

A sparkling in-ground pool is visible in the foreground, surrounded by a spacious patio. Lounge chairs are positioned along the deck, offering views of the lagoon. Lush palm trees provide shade, while a clear sky enhances the tranquil atmosphere of the waterfront setting.

4.99 out of 5 average rating, 151 reviews

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

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.

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 168 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

A charming cottage features a covered deck with a dining table and chairs, positioned beside a pool. Lush palm trees and tropical plants surround the area, adding greenery. The pool water is clear and inviting, with a depth marking visible at the edge.

4.95 out of 5 average rating, 364 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Apartment in Key Colony Beach

A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.

4.91 out of 5 average rating, 197 reviews

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.

4.86 out of 5 average rating, 341 reviews

A three-story historic building is framed by palm trees and tropical foliage. White decorative railings and an ornate archway lead to the entrance, while soft sunlight brightens the exterior's yellow siding. The inviting architecture complements the serene surroundings.

Holiday home in Key West

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.

5 out of 5 average rating, 103 reviews

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

4.89 out of 5 average rating, 258 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Home in Upper Sugarloaf Key

The bungalow stands illuminated against a night sky, surrounded by swaying palm trees. Soft reflections shimmer on the water's surface, while the sandy beach extends along the shoreline. The structure features large windows, showcasing a welcoming interior visible from outdoors.

4.94 out of 5 average rating, 105 reviews

Lighthouse - Beach Houses Key West

If you’re reading this, you’re already on the path to paradise! Thank you for considering us for your dream vacation—we can’t wait to host you. Our amazing Lighthouse is a 2 bed 1 bath Loft Bungalow sitting just a few feet from our private beach. The master bedroom loft is accessed by a spiral stair, and has a beautiful bird’s eye view of the Atlantic Ocean. Our nautical inspired living room leads outside to an exterior deck facing the beach perfect for peaceful mornings.

A serene waterfront scene is captured at sunset, featuring palm trees, boat docks, and a gently reflecting harbor. A large boat is tied up alongside the dock, with colorful lights and silhouettes of the surrounding structures visible in the background.

4.91 out of 5 average rating, 230 reviews

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

4.9 out of 5 average rating, 399 reviews

Three modern Aqua Lodges are positioned on water, featuring white exteriors and blue roofs. Each lodge has a furnished deck with chairs, providing relaxed seating options. A smooth, concrete path runs alongside the lodges, leading to a marina setting with sailboats in the background.

Villa in Marathon

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!

A modern two-story home with a spacious outdoor area featuring a private pool. Comfortable lounge chairs surround the pool, and a staircase leads to the upper level. The structure is complemented by a rooftop terrace with a sail shade, enhancing the coastal atmosphere.

4.97 out of 5 average rating, 124 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

As published in Condé Nast Traveler, this is one of the best Airbnb's in Florida. Newly Built two story Tropical Oasis with pool has been thought-out meticulously. An open, very light & spacious floor plan, carefully appointed furnishings, and great location provide the perfect surroundings. Decorated with a Zen sensibility, It’s outdoor Patio deck and Rooftop Terrace extends your living space into the private quiet ocean setting with panoramic views

4.92 out of 5 average rating, 174 reviews

A serene pool area features a clear blue water swimming pool surrounded by lounge chairs and umbrellas. A lush landscape of palm trees and green foliage complements the setting, with a charming cottage visible in the background.

Townhouse in Key West

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Popular amenities for Key West rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 53 reviews

A serene waterway is framed by charming homes, with a white boat bobbing gently at the dock. The sky displays a vibrant sunset in shades of orange and pink, reflecting softly on the calm water, creating a peaceful waterfront scene.

Home in Cudjoe Key

Waterfront, Dock, Pool, Pickleball, near Key West!

A spacious wooden dock extends over calm waters, featuring a thatched tiki hut and several lounge chairs in a soft blue hue. Lush greenery surrounds the area, complemented by a serene sky at sunset, providing a peaceful atmosphere for relaxation.

5 out of 5 average rating, 32 reviews

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

4.93 out of 5 average rating, 186 reviews

Home in Cudjoe Key

106- Newly Renovated House with Oceanview and Pool

A tranquil pool is surrounded by lush palm trees, offering a serene atmosphere. The water reflects sunlight, while seating options are provided by the poolside. The design features a curved edge and a spa section, creating an inviting outdoor retreat.

5 out of 5 average rating, 9 reviews

The Roseate House at Grassy Key

4.95 out of 5 average rating, 128 reviews

A paved outdoor patio features two lounge chairs and a small round table, surrounded by tropical plants and palms. The tranquil canal is visible in the background, offering a serene waterfront view.

Home in Key Colony Beach

Waterfront Home 37.5-ft dock, Cabana Club Included

4.82 out of 5 average rating, 285 reviews

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

Home in Cudjoe Key

Nov. & Dec. 50% off! Oceanfront, 4 Bikes 2 Kayaks

A private pool area is surrounded by lush greenery, with chaise lounges arranged around the pool. The wooden deck provides space for outdoor furniture, including a dining set. Bright natural light filters through the trees, creating an inviting atmosphere.

5 out of 5 average rating, 3 reviews

Jasmine Jewel at The Annex

4.97 out of 5 average rating, 115 reviews

A serene view of a canal populated by several pelicans floating on the water's surface. Palm trees line the shore, and colorful houses are visible in the background. A boat is docked nearby, enhancing the peaceful coastal scene.

Home in Key Colony Beach

Waterfront House with 37 ft Dock & Cabana Club

Apartment rentals with a pool

A spacious outdoor patio is viewed, featuring a dark wooden table and black wicker chairs. A decorative rope centerpiece is placed on the table. The horizon displays a vivid sunset with shades of orange, pink, and purple, casting a serene reflection over the calm water.

4.96 out of 5 average rating, 80 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

4.94 out of 5 average rating, 101 reviews

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Apartment in Marathon

Canal View Condo w/ Pool, Balcony & Bar

5 out of 5 average rating, 26 reviews

A beachfront view captures a well-maintained property featuring multiple levels of balconies. Sun loungers are arranged on the sandy shore, accompanied by vibrant beach umbrellas. The ocean's gentle waves meet the sand under a clear blue sky, enhancing the coastal atmosphere.

Apartment in Marathon

*NEW LUXURY*Sea Glass-Beach/Pool

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.89 out of 5 average rating, 148 reviews

Tropical Escape at Sunrise

A private balcony features a round table set with soft blue plates and glasses of juice. Comfortable chairs surround the table, with a bowl of fresh fruit placed in the center. Lush greenery and partial ocean views contribute to a serene outdoor setting.

4.85 out of 5 average rating, 160 reviews

Anchor Drop modern elegance upgrades throughout vi

A spacious living area is furnished with blue sofas and an accent chair. Large windows allow natural light to fill the room, while tropical plants add a touch of greenery. A ceiling fan and decorative wall art complement the inviting ambiance.

5 out of 5 average rating, 7 reviews

Fair Winds @ The Foundry~ Frolic On Duval St

An open-concept living area offers a view of comfortable seating arrangements and natural light. The kitchen features a marble countertop and modern appliances. A balcony is visible through sliding glass doors, surrounding greenery enhancing the serene environment.

4.9 out of 5 average rating, 39 reviews

Key Lime Paradise 2BR w/ Pool, HotTub, Near Beach!

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

5 out of 5 average rating, 42 reviews

EYW Getaway

Other holiday rentals with a pool

5 out of 5 average rating, 5 reviews

Parrot Perch by AvantStay | Week-Long Stays

4.98 out of 5 average rating, 55 reviews

A modern living area is presented with a comfortable grey sofa and two patterned chairs facing a large sliding door. Natural light fills the space, illuminating a textured wood coffee table and a side table with a lamp. A mounted television displays vibrant sunset imagery.

Flat in Key West

Newly Renovated 2/2 Bath Condo, with shared pool

An inviting outdoor space features comfortable seating and a hot tub, surrounded by lush greenery. A large screen is set up for movie nights, and ambient lighting enhances the evening atmosphere as the sun sets.

5 out of 5 average rating, 55 reviews

Marathon Keys Escape • Pool • Hot Tub • Near Beach

A spacious swimming pool is surrounded by lush tropical greenery and lined with lounge chairs. Tiki-style huts provide shaded areas for relaxation, while the pool's clear blue water reflects the vibrant sky, creating a serene and inviting environment.

5 out of 5 average rating, 26 reviews

Funky Chicken Cottage with Shared Pool in Paradise

5 out of 5 average rating, 27 reviews

An open living space is featured, highlighted by a round dining table surrounded by comfortable seating. A large television is mounted on the wall, while light-colored walls enhance the bright atmosphere. A serene coastal artwork depicting a pier adds a calming touch to the decor.

Home in Key Colony Beach

Bohemian Beach Bungalow

5 out of 5 average rating, 4 reviews

A private balcony features a round table surrounded by four chairs, providing a comfortable space to enjoy the ocean view. Lush greenery and palm trees are visible in the background, with the tranquil ocean further enhancing the outdoor setting.

Flat in Key West

Oceanview condo w/pool, jacuzzi

5 out of 5 average rating, 83 reviews

A private backyard features a heated pool surrounded by tropical landscaping. Lounge chairs are positioned on the wooden deck beside the pool. The two-story home includes large glass doors that open onto the deck, providing easy access to outdoor spaces.

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located