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, 113 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 large heated Olympic-sized pool is set within a tropical landscape, surrounded by palm trees and lounging chairs. The inviting blue water reflects the sky and is complemented by the nearby resort building, which features multiple levels and balconies.

4.92 out of 5 average rating, 199 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. Thank you for understanding. Spalling work hs begun on the balconies of the other building this may impact your enjoyment of the pool

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, 453 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.

A welcoming entrance features a door labeled '8A' and is flanked by two red chairs with blue and white striped cushions. A small table rests between them, surrounded by potted plants. A window offers a glimpse of natural light within the unit.

4.86 out of 5 average rating, 109 reviews

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat sofa and a small dining table with 2 chairs. Private bathroom. AC will keep you cool. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Optional boat slip can be rented for $25/night Efficiency has a 2 person maximum occupancy - no exceptions.

4.85 out of 5 average rating, 131 reviews

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.

Flat in Key Colony Beach

Beachside Unit 22 - Private Beach on Atlantic

Unit 22 Details: Main Floor, Walk-in Shower, 2 Queen Beds and Queen Sofa Pull-out, Maximum Occupancy 4 Guests, Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

4.98 out of 5 average rating, 529 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.

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.

4.91 out of 5 average rating, 305 reviews

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

Starr's Suite features a King Pillow-Top Memory Foam mattress. Renovated in 2010, it features a tumbled marble shower, granite counter-tops in kitchen with dishwasher and vanity. Tommy Bahama bath amenities are provided, as well as coffee, creamer and sugar. 56” Smart TV (bring UN/PW for Netflix, Amazon, etc. to watch your favorite shows). Private Solana spa in your private courtyard. Daily housekeeping is provided. Use of 2 heated pools.

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.

4.85 out of 5 average rating, 26 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 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, 159 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 private deck area features a Jacuzzi in the foreground, surrounded by lush greenery. French doors open to a cozy interior space, showcasing a seating area and warm natural light. Outdoor seating is visible, inviting relaxation.

4.78 out of 5 average rating, 157 reviews

Mango Hideaway @ the Eyebrow House off Duval

Mango Hideaway – Historic Old Town Suite with Private Spa Escape to the Mango Hideaway, a cozy vacation suite in a charming historic eyebrow house at 516 Olivia Street in the heart of Old Town Key West. Just a short stroll to Duval Street, the Ernest Hemingway Home, Key West Lighthouse, and Mallory Square, this location puts you steps from top restaurants, live music, beaches, and iconic attractions.

A light-filled living room features a blue sofa, a comfortable chair, and a glass coffee table. Large sliding doors open to a balcony with ocean views. A soft area rug lies on the tiled floor, adding warmth to the space, while sunlight illuminates the room.

4.97 out of 5 average rating, 109 reviews

Beachfront Condo w/ Ocean Views in Marathon

Beautifully decorated 2nd floor end unit with stunning panoramic ocean views from the balcony, living room and master bedroom. Two bedrooms / two full bathrooms and washer and drier in unit. Full kitchen. Directly on the beach! Beach chairs, umbrellas and towels provided for you. Guests have access to the heated swimming pool, tennis court and beach. Master bedroom king-size memory foam mattress

The spacious studio features two large beds with light bedding. A contemporary sofa and chairs are arranged around a coffee table in the living area. The room includes a flat-screen TV mounted on the white wall, with ceiling fans and wooden flooring enhancing the bright atmosphere.

4.88 out of 5 average rating, 292 reviews

#203 Key West Suites

Welcome to your charming private studio apartment right on Duval street! Built in 1919, it used to be called the Central Hotel because it’s located at the most central location on Duval Street bordering Southard Street and Duval Street! Although this a vacation rental and not a hotel per se with a lobby etc, we kept hotel in the name in keeping with historic nostalgia, "Key West Suites Hotel"

Popular amenities for Key West apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

The exterior of a charming house is presented with a covered front porch, featuring white rocking chairs. Lush palm trees and greenery provide a tropical backdrop, while a gravel pathway leads to the entrance. Nearby, parked vehicles are visible, hinting at convenient access.

4.79 out of 5 average rating, 159 reviews

Mesa House Dos - One block from Duval St

A comfortable room features a spacious bed with crisp white linens, positioned against a coral-themed accent wall. Natural light streams through a window with white shutters. A small dining table and chairs complement a kitchenette area, while a large mirror enhances the sense of space.

4.87 out of 5 average rating, 1,616 reviews

At Mine | Lovely Suite steps from Duval Street

A welcoming entrance pathway, lined with lush greenery, leads to a light green exterior of the studio condo. A porch is visible at the front, featuring a blue chair. The area is subtly accented by tropical plants and decorative stones.

4.58 out of 5 average rating, 12 reviews

Coconut Mallory Studio-401

The street view showcases a vibrant atmosphere, featuring a sign for 'Old Town Suites' and directional signage toward Duval Street. Palm trees line the sidewalk, and a bus is seen passing, indicating easy access to local attractions. Bright blue skies frame the scene.

4.78 out of 5 average rating, 260 reviews

Old Town Suites - 2 Bedroom Suite #2

A vibrant yellow two-story building features an inviting facade with terracotta roofing and large windows. Lush greenery surrounds the entrance, enhancing the tropical atmosphere. A staircase leads to the second floor, offering access to outdoor living spaces.

5 out of 5 average rating, 6 reviews

Boot Key Harbor Penthouse

A cozy living space features a blue sofa adorned with colorful throw pillows, set against a vibrant area rug with floral patterns. Decorative artwork and a staircase with a unique railing design add character to the room, while additional art pieces decorate the walls.

4.88 out of 5 average rating, 58 reviews

1BR with balcony & lighthouse view, steps to Duval

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.

OCEAN community, perfect condo

A refreshing pool area is surrounded by green palm trees and blue umbrellas. Lounge chairs are arranged neatly around the pool, while tables with chairs provide seating for guests. The clear blue sky enhances the inviting atmosphere of the community space.

4.88 out of 5 average rating, 114 reviews

Penthouse in Paradise

Private apartment rentals

The Cozy Nest.

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.

Best Resort in Key West, 2BD/2BA

A large swimming pool is surrounded by palm trees and lounge chairs. Umbrellas and shaded areas are present for guest comfort. The area is illuminated in a blue evening light, with a relaxed atmosphere enhanced by nearby dining options.

4.56 out of 5 average rating, 71 reviews

Accessible Deluxe 1 Bedroom King Suite w/ Balcony

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, 153 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, 846 reviews

Duval Balcony Spanky's Retreat

A spacious living area is presented, featuring a comfortable sectional sofa adorned with decorative pillows. A light-colored coffee table sits in front, complemented by a small plant. Large sliding glass doors allow natural light and provide views of the outdoor space.

4.94 out of 5 average rating, 17 reviews

Relax with the whole family at this peaceful place

A decorative wooden sign is mounted on a white post, featuring the text 'Center Court Historic Inn & Cottages' in bold letters. Lush tropical greenery surrounds the area, with palm trees and vibrant plants visible, creating a welcoming entrance to the property.

4.95 out of 5 average rating, 340 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

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, 762 reviews

Duval Balcony - Suite Mischief

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.

4.89 out of 5 average rating, 90 reviews

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

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, 59 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

New place to stay

The Grand Turk | Spectacular Sunset View, Private

A tranquil pool area features lounge chairs arranged around a crystal-clear pool. Palms sway gently nearby, and a tiki bar with a roof can be seen in the background, overlooking calm waters. The sky transitions to a soft blue as evening approaches.

5 out of 5 average rating, 4 reviews

Marathon Studio on Lovely Gulf Front Resort

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.