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Vacation rentals with a pool in Sunset Key

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sunset Key

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The image captures a circular pool surrounded by palm trees and a wooden deck. Lounge chairs in blue are arranged for relaxation. A light-colored cottage is visible in the background, creating an inviting atmosphere. The sky above is bright and partly cloudy.

Home in Key West

4.95 out of 5 average rating, 358 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.

Cottage in Cudjoe Key

4.93 out of 5 average rating, 137 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

The image showcases a bright pool area surrounded by lush tropical foliage. A two-story wooden building features multiple balconies, enhancing the serene environment. Several lounge chairs are positioned on the pool deck, inviting relaxation under the sunlight.

Vacation home in Key West

4.86 out of 5 average rating, 337 reviews

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.

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.

Condo in Key West

4.89 out of 5 average rating, 252 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.

A clear blue sky with scattered clouds is visible above the pool area. Palm trees line the edge of the space, providing a tropical feel. A rectangular pool and a smaller octagonal pool are present, surrounded by lounge chairs and an open expanse of sandy ground.

Home in Cudjoe Key

4.97 out of 5 average rating, 167 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

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

4.92 out of 5 average rating, 165 reviews

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

Home in Cudjoe Key

4.9 out of 5 average rating, 115 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.

A scenic view of the waterfront reveals a calm harbor lined with boat slips. The vibrant blue water reflects the sky, while a tiki hut and chaise lounge chairs surround a heated pool in the foreground, enhancing the coastal ambiance.

Condo in Key West

4.87 out of 5 average rating, 220 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

A tranquil view features a sparkling turquoise pool surrounded by tropical palms. A private fence encloses the area, providing a clear sightline to the ocean's horizon under a bright blue sky. Several lounge chairs are positioned poolside, inviting relaxation in the sun.

Home in Cudjoe Key

4.89 out of 5 average rating, 243 reviews

101- Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

The expansive outdoor pool is framed by palm trees and surrounded by lounge chairs with blue umbrellas. The area is well-lit and features a shaded pavilion. The surrounding building showcases tropical landscaping, providing a relaxing atmosphere for guests.

Apartment in Key West

4.9 out of 5 average rating, 152 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.85 out of 5 average rating, 257 reviews

Key West Luxury Houseboat at Yacht Club Resort

PANORAMIC Ocean Views - POOL 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, 500 square foot Rooftop Sky-Deck - 2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV, 42 inch TV, 32 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

A spacious outdoor area is depicted, with an Olympic-size swimming pool surrounded by lounge chairs and umbrellas. Lush palm trees and landscaped gardens frame the scene, while a sandy beach and ocean are visible in the background, enhancing the resort-like atmosphere.

Condo in Key West

4.78 out of 5 average rating, 300 reviews

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!

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Popular amenities for Sunset Key rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

A two-story waterfront home is situated under a clear blue sky, surrounded by palm trees and lush greenery. The property features a bright white exterior with a balcony, along with a manicured yard of decorative rocks and native plants.

Home in Cudjoe Key

4.91 out of 5 average rating, 56 reviews

Keys Island Villa - Venture Out Home 354

Home in Cudjoe Key

5 out of 5 average rating, 3 reviews

Oceanfront 2BR in Venture Out - 35’ Dock + Pool

Home in Key West

4.94 out of 5 average rating, 115 reviews

Paradise found

Home in Cudjoe Key

4.81 out of 5 average rating, 280 reviews

Oct. Special 50% off! Waterfront, 4 Bikes 2 Kayaks

A private pool glistens under the sun, surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. In the background, a tiki palapa with a thatched roof offers shaded seating, complemented by lush tropical foliage and a distant pink house.

Home in Summerland Key

4.9 out of 5 average rating, 42 reviews

Pelico Palms Sunset Suites

An aerial view showcases a spacious waterfront home surrounded by lush greenery and palm trees. A private heated pool is bordered by a white fence, with lounge chairs and umbrellas nearby. A boat dock extends into the water, enhancing the serene setting.

Home in Summerland Key

5 out of 5 average rating, 4 reviews

Waterfront Beach House with Dock & Heated Pool!

A spacious pool area is highlighted by a heated swimming pool surrounded by a safety fence. Lounge chairs are positioned for relaxation, with the house elevated above, showcasing a wraparound balcony and greenery in the background. The clear blue sky adds to the inviting atmosphere.

Home in Cudjoe Key

4.81 out of 5 average rating, 95 reviews

Palm Breezes! Room for Everyone on the Ocean.

Home in Cudjoe Key

4.86 out of 5 average rating, 110 reviews

Waterfront Sanctuary in the Keys!

Condo rentals with a pool

A community pool is shown, featuring a clear blue water surface with visible lane markings. Surrounding the pool are lounge areas with light-colored decking and palm trees in the background, adding to the open and airy feel of the space.

Condo in Key West

4.82 out of 5 average rating, 288 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

A cozy sleeping area features a spacious bed with crisp white linens, framed by warm wooden walls. Light streams in through multiple windows with plantation shutters. A wall-mounted TV and a small shelf are positioned across from the bed, and a ceiling fan provides ventilation.

Condo in Key West

4.9 out of 5 average rating, 31 reviews

Chagall’s Corner | Newly Remodeled!

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.

Condo in Key West

4.96 out of 5 average rating, 80 reviews

Oceanfront 3 bed condo Ocean Edge w/ optional slip

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.

Condo in Key West

4.89 out of 5 average rating, 147 reviews

Tropical Escape at Sunrise

Condo in Key West

4.89 out of 5 average rating, 35 reviews

New Listing! Key Lime Paradise/Condo

A spacious outdoor pool area is surrounded by lush greenery and palm trees. Lounge chairs are positioned around the pool for relaxation. A shaded area is available, providing a place for guests to gather. Clear water reflects the blue sky above.

Condo in Key West

4.99 out of 5 average rating, 75 reviews

The Palms

A spacious balcony overlooks the ocean, featuring blue Adirondack chairs and a dining table. Lush greenery and palm trees frame the view. The sky is clear and sunny, reflecting on the water, creating a serene atmosphere.

Condo in Key West

5 out of 5 average rating, 6 reviews

Southermost Serenity an exclusive 3 Bedroom Ocean

Top guest favorite

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.

Condo in Key West

5 out of 5 average rating, 40 reviews

EYW Getaway

Other vacation rentals with a pool

Condo in Key West

5 out of 5 average rating, 4 reviews

Southard Quarter at Truman Annex | Walk to Duval

An open living area is showcased with a light brown leather sofa and a modern dining set positioned by large windows, allowing natural light and views of the marina. A sleek kitchen with a white countertop and stainless steel appliances is visible, creating a welcoming gathering space.

Boat in Key West

4.93 out of 5 average rating, 54 reviews

Waterfront & Heated Pool - Awai's Floating Villa

A private pool area is surrounded by lush greenery and palm trees. Lounge chairs are arranged around the shallow pool, providing a relaxing space for guests. The paved area includes a small seating arrangement under a canopy, offering shaded spots to unwind.

Apartment in Key West

4.87 out of 5 average rating, 1,562 reviews

At Mine | Lovely Suite steps from Duval Street

A sandy beach transitions to calm waters, framed by palm trees and greenery. Sun loungers are arranged neatly along the shore. A private spiral staircase leads to the beach, while a wooden dock extends into the water, inviting leisurely excursions.

Condo in Key West

4.84 out of 5 average rating, 128 reviews

Ocean Front Suite with Direct Beach Access

A spacious outdoor patio is displayed, featuring a dining table surrounded by six chairs. The railing offers a view of Garrison Bight Marina, where boats are docked and palm trees sway. Sunlight casts patterned shadows across the patio floor.

Apartment in Key West

4.89 out of 5 average rating, 54 reviews

Key West Condo 2B/2B with Pool & Boat FREE Slip

An outdoor lanai features a round glass table surrounded by four green cushioned chairs. A ceiling fan is mounted above, and a tree partially shades the area, providing a serene setting for relaxation.

Home in Key West

5 out of 5 average rating, 8 reviews

Roost Haven w/ free private parking spot

A clear pool surrounded by palm trees offers a serene atmosphere. Lounge chairs are arranged around the pool, inviting relaxation. The property features well-maintained landscaping, enhancing the tranquil environment.

Townhouse in Key West

4.96 out of 5 average rating, 284 reviews

Stunning Townhouse * Full kitchen! * Sleeps 6

Top guest favorite

A motor yacht glides over the turquoise waters, leaving a wake in its path. The skyline of a city is visible in the distance, complemented by a clear blue sky and scattered clouds. The scene captures a moment of elegance and adventure on the open water.

Boat in Key West

5 out of 5 average rating, 14 reviews

FREE TIME 50’ 2 Cabin Yacht-Key West

Destinations to explore