Apartment holiday rentals in Key West

The living room features two sofas in contrasting colors with decorative cushions. A small white table is centered between them, and light streams in through windows adorned with wooden shutters. A ceiling fan adds to the airy atmosphere.

4.84 out of 5 average rating, 126 reviews

King Bed | Key West *Best Downtown Locations *Cool

AUGUST, SEPTEMBER, OCTOBER – We have significantly lowered our prices for the off-season. Please use part of the discount to purchase travel insurance at the time of booking. AirBnB Cancellations and Major Disruptive Events Policy excludes weather or natural conditions that are common enough to be foreseeable in a given location. Hurricanes are considered common and foreseeable in Florida between June and November, with peak activity typically occurring in August, September, and October.

A spacious bed is framed by elegant side tables, each topped with a softly glowing lamp. Above the headboard, three framed artworks create a balanced focal point. Decorative pillows add a touch of color, while a leafy plant provides a natural element to the serene space.

4.95 out of 5 average rating, 463 reviews

Studio Blu -Hip Studio/Old Town

*Recent Update (2025): We’ve made a wonderful upgrade to the studio bathroom — it’s now fully enclosed with walls extending to the ceiling and a new exhaust fan for ventilation. Situated in the heart of the Cuban district, just steps from arguably the best café con leche in Key West, this bright and breezy studio apartment is minutes from everything on the island. No car needed — bikes and beach chairs are provided free of charge so you can explore at your own pace.

4.98 out of 5 average rating, 542 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

1B/1B condo located in Old Town less than 1/2 block from Duval St. & a couple blocks from the Southernmost Point, Hemingway House & many other Key West attractions. Bella Vita accommodates 2 adults only and features a large porch with chairs & table, living room with leather sofa, galley kitchen with bar seating, king-size bed with Tempurpedic mattress, desk area, bathroom with large walk-in shower, wi-fi, sound machine, 2 Smart TVs & DVD players.

5 out of 5 average rating, 6 reviews

New! Waterfront Views | Pool & Tiki Bar

Be our first guest at the MYSTIC MERMAID a brand new built 1BR/1BA Waterfront Villa that sleeps up to 4 guests! This luxury retreat is located on a scenic canal with marina slips right outside its' door! Enjoy amazing resort amenities including a pool, Tiki Bar, restaurant, pickleball & volleyball courts, fitness center, complimentary breakfast & more. Perfectly situated in the middle of the FL Keys making it the ultimate Florida Keys escape!

A light and airy living area features a modern blue sofa adorned with patterned throw pillows. A wooden coffee table sits in front, complemented by a tall indoor plant. A full-length mirror reflects the space, while natural light brightens the room through the patio door.

4.89 out of 5 average rating, 37 reviews

Duval Corner - Pet friendly with Balcony

Welcome to Duval Corner! A beautifully updated one-bedroom condo in the heart of Downtown Key West. This second-floor retreat is perfect for travelers wanting to be steps from it all. Within walking distance to iconic attractions like the Southernmost Point, The Ernest Hemingway Home, and Mallory Square, plus dining hotspots such as Blue Heaven, 7 Fish, and Louie's Backyard; Duval Corner is the ideal base for your Key West adventure.

The entrance to the efficiency is framed by tropical landscaping and palm trees. Red umbrellas shade picnic tables while a charcoal grill is available nearby. Colorful fish signs direct guests towards unit 8A, enhancing the inviting exterior ambiance of the property.

4.78 out of 5 average rating, 78 reviews

Small Efficiency, 8b

Small efficiency located about 50 yards from the ocean. Unit has a queen bed, single chair, small dining table for two. A very small kitchen area, microwave and sink. Medium size refrigerator with freezer. Mini split ductless AC. Private bathroom with shower. Comfortable 3-seat sofa on porch. Access to shared pool. Optional boat slip can be rented for $25/night. The efficiency has a two person maximum occupancy.

4.92 out of 5 average rating, 255 reviews

Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!

Historic 1880's Cigar Maker's cottage completely renovated. 1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV's, Full kitchen with granite counter tops, new stainless steel appliances. A newly remodeled bath with tumbled marbled tile, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!

An open concept studio apartment features a modern kitchen with stainless-steel appliances, including a coffee maker and oven. A dining table with black chairs is positioned near the kitchen. In the background, a spacious bed is visible, illuminated by natural light from large windows.

4.86 out of 5 average rating, 256 reviews

The Bartlum - Steps to Duval Street

Welcome to the Bartlum, a historic and luxurious studio apartment just steps to Duval Street. This studio, located on Caroline St, has been designed with comfort in mind, offering large windows for natural sunlight and plenty of space to spread out. Enjoy an updated kitchen, spacious bathroom, open concept layout, and all the hot spots of Key west within walking distance!

A cozy bedroom features a spacious bed dressed in white linens and decorative pillows. Natural light filters through a window adorned with wooden blinds. A mirror and wicker accents complement the tropical wall decor, while dark hardwood flooring adds warmth to the space.

4.96 out of 5 average rating, 126 reviews

Duval Street Suites full kitchen, free parking, he

Paradise Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. In historic Old Town, Key West. Free parking available and the pool is privately located behind the building . Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

A shared pool area is showcased overlooking Garrison Bight Marina. Lounge chairs are arranged around the pool, with a thatched gazebo providing shaded seating. The marina is visible in the background, featuring moored boats and palm trees against a clear sky.

4.92 out of 5 average rating, 101 reviews

Waterfront Condo FREE Slip & Pool 2B2B in Key West

🌴 Key West Waterfront Paradise – FREE Dockage Included! Wake up to breathtaking marina views, unwind in the heated pool, and walk or bike to Duval Street in minutes. Enjoy a spacious condo with a private balcony, exclusive boat slip, and all the comforts you need for an unforgettable stay in the heart of Key West.

A charming building situated on a bustling street features a wraparound porch adorned with white railings. Palm trees offer shade, and an American flag adds a pop of color. Nearby vehicles are parked along the lively street, showcasing the vibrant atmosphere of the area.

4.83 out of 5 average rating, 252 reviews

#204 Key West Suites

Welcome to your charming private studio apartment right on Duval street! Built in 1919, it was called the Central Hotel because it’s located at the most central location on Duval bordering Southard Street and is on the second floor overlooking both Duval and Southard Streets.

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.

4.91 out of 5 average rating, 162 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

Popular amenities for Key West apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

4.89 out of 5 average rating, 9 reviews

Quiet Canalfront Retreat • Near Sombrero Beach

A lush garden expanse is depicted, featuring vibrant greenery and colorful flowers. Palm trees sway in the gentle breeze, while the ocean is visible in the background. A pool is nestled within the landscaped area, complemented by a shady outdoor dining space under a canopy.

5 out of 5 average rating, 3 reviews

Best Resort in Key West, 2BD/2BA

4.94 out of 5 average rating, 48 reviews

Private room in Key West

Duval street downtown

A bright and airy bedroom features a spacious bed with a checked blanket. A white dresser sits against the wall beside a decorative fish and tall red accents. Natural light enters through double doors that lead to a small balcony, enhancing the tranquil atmosphere.

4.83 out of 5 average rating, 296 reviews

Sunrise - Best Downtown Locations

A well-lit bedroom features wooden paneling and a spacious bed with a patterned blanket. Shelves filled with books are situated beside the bed. A sliding glass door leads to an outdoor area, while warm lighting enhances the cozy atmosphere.

4.89 out of 5 average rating, 54 reviews

Apartment at Safe Harbor Marina

An oceanfront heated pool is presented, with clear water reflecting the sky. Surrounding palm trees harmonize with the serene coastal backdrop, and lounge chairs offer seating options. The pool area is enclosed by a fence, providing a defined relaxing space with views of the ocean.

5 out of 5 average rating, 7 reviews

OCEAN community, perfect condo

The resort's outdoor pool area features a clear blue pool surrounded by lounge chairs. Palm trees are seen in the background, alongside a two-story building. Red umbrellas provide shade for guests enjoying the poolside atmosphere under a bright blue sky.

4.61 out of 5 average rating, 1,183 reviews

Standard 1 Bedroom King Suite with Balcony

4.71 out of 5 average rating, 75 reviews

Charming 1BR two-story apartment with 2 balconies

Private apartment rentals

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.86 out of 5 average rating, 136 reviews

Beachside Unit 22 - Private Beach on Atlantic

A welcoming bedroom is highlighted by a spacious bed adorned with vibrant floral bedding. Two wall art pieces complement the green and wood tones, while natural light filters through the dual windows with blinds. A bedside table with a lamp adds to the cozy ambiance.

4.91 out of 5 average rating, 112 reviews

Duval Street Suites full kitchen and heated pool

The entrance to a charming village is marked by an archway adorned with colorful lettering and a distinctive emblem. Lush palm trees line the quiet street, which is paved with bricks, and features colorful buildings along either side.

4.92 out of 5 average rating, 166 reviews

Duval Street Suites with full kitchen heated pool,

A lively street scene showcases a classic two-story building featuring blue shutters and a prominent sign for Venter Surf & Sport. People are seen browsing the shop, while bicycles are parked along the curb, indicating a vibrant, active atmosphere in the heart of Duval Street.

4.91 out of 5 average rating, 858 reviews

Duval Balcony Spanky's Retreat

A landscaped outdoor area features a paved path surrounded by lush tropical plants and trees. Seating options include colorful adirondack chairs and tables with umbrellas, inviting relaxation under soft lighting. The space creates an ambient atmosphere for evening gatherings.

4.67 out of 5 average rating, 15 reviews

Hogfish Hideaway Two Bedroom Condo

A comfortable living area features a patterned sofa and matching loveseat, organized around a glass-top dining table with woven placemats. The space is illuminated by natural light from two windows, while a wall-mounted air conditioning unit provides climate control.

4.88 out of 5 average rating, 777 reviews

Duval Balcony - Suite Mischief

A private courtyard is displayed, featuring a hot tub, two chairs, and a small table. The entrance to the suite is visible with elegant French doors that open to the interior. Lush greenery enhances the tranquil ambiance, with a striped awning offering partial shade.

4.92 out of 5 average rating, 314 reviews

Starr's Suite - 2 person K Suite w/Private Spa!

The spacious studio features two king beds, a leather sofa, and a wooden dining area. Large windows allow natural light to fill the room, showcasing a relaxation space with a wall-mounted TV and a full kitchen visible in the background.

4.86 out of 5 average rating, 301 reviews

#201 Key West Suites

Apartment rentals with a hot tub

A bright living area features light-colored furniture, including a comfortable sofa and armchair. A wooden coffee table is centrally placed. Art displays adorn the walls, enhancing the inviting ambiance. Nearby seating accommodates dining for four, with large windows allowing natural light to flow in.

4.87 out of 5 average rating, 93 reviews

Castaway Cove: Pet-friendly 2/2 condo near beach!

5 out of 5 average rating, 3 reviews

Sunset Harbor 2 bed Ocean views!

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.

4.98 out of 5 average rating, 64 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

The resort pool is surrounded by palm trees and lush greenery, creating a serene atmosphere. Several lounge chairs are arranged neatly along the pool's edge, inviting relaxation under the clear blue sky. Breezy shades from umbrellas offer spots for comfortable seating.

Hyatt Beach House, Key West - 2 bedroom suite

The property is positioned near the shoreline, featuring a modern design with multiple balconies. Lush palm trees frame the exterior, while a landscaped garden adds greenery. The serene ocean can be seen in the background under a twilight sky.

4.86 out of 5 average rating, 7 reviews

Hyatt Windward Pointe! Great Location!

The image captures a scenic view of a zero-entry pool surrounded by lush palm trees and manicured landscaping. Several lounge chairs are positioned nearby. In the foreground, a straw hat and two beverages are placed on the poolside, creating a relaxed atmosphere.

Hyatt Resort Club at Beach House. 2 Bedroom/2 Bath

An inviting outdoor lagoon pool is surrounded by lush tropical landscaping and tall palm trees. A spacious deck with sun loungers provides ample space for relaxation. The pool area is well-maintained, showcasing clear blue water under bright skies.

2 BR @ Hyatt Beach House Resort

A spacious pool area features a large swimming pool surrounded by lounge chairs and vibrant blue umbrellas. Lush palm trees provide shade, and ocean views are visible in the background, enhancing the tranquil atmosphere of the outdoor space.