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.

4.83 out of 5 average rating, 142 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 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.

4.84 out of 5 average rating, 140 reviews

Penthouse in Paradise

Coconut Mallory is a waterfront private community that provides resort amenities. Hop in one of the two on-site pools to cool down after soaking up the sun at Smathers Beach, Key West's largest public beach just 2 miles away. There is also a Jacuzzi and a picnic area with BBQs for guest use. This unit is a two bedroom two bath. It also features two off street parking spaces included. *The Master Tub is not to be used per the community as leaks have occurred in other units before.

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, 470 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.

4.95 out of 5 average rating, 354 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

This Historic unit from 1880's has a kitchen, platform Pottery Barn King 14" memory foam bed with multiple basket drawers underneath for storage, large shower. Large private deck with 2 person spa, hammock, outdoor sofa and table/chairs. Bluetooth speaker, Alexa. Private gated compound and gated entrance to Honeymoon Hideaway. Renovated August, 2019 with new full bathroom and designer kitchen with dishwasher, 2 burner stove, refrigerator with freezer, microwave!

4.98 out of 5 average rating, 554 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 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.

4.79 out of 5 average rating, 162 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 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.

4.88 out of 5 average rating, 104 reviews

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

Welcome to the tranquil, tucked away community of Sunrise Suites in beautiful Key West, Florida. When you choose to spend your vacation with us at the pet-friendly Castaway Cove Condo, you will be just 1 mile from Smather's Beach and a quick 10 minute drive to the fun and excitement of downtown Duval Street with tons of restaurants, bars, art galleries, museums, live music and people watching.

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, 261 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 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.

4.93 out of 5 average rating, 116 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.

4.92 out of 5 average rating, 119 reviews

Duval Street Suites full kitchen and heated pool

The Little Palm Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking the pool in historic Old Town, Key West. Located in the middle of everything yet quiet and away from it all. This space is truly unique and sure to please all ages.

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, 163 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

A warm-toned room features wood-paneled walls accented by natural light from two windows. A spacious bed with an orange bedspread is positioned alongside a cozy seating area comprising two cream-colored couches facing a small round table.

4.83 out of 5 average rating, 876 reviews

Duval Balcony - Street Suite

5 out of 5 average rating, 3 reviews

Two Bedroom Condo W/ Resort Amenities! 210

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, 876 reviews

Duval Balcony Spanky's Retreat

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, 62 reviews

Apartment at Safe Harbor Marina

4.86 out of 5 average rating, 310 reviews

#201 Key West Suites

A vibrant sunset casts warm hues over the beach, where two figures stand with arms outstretched, silhouetted against the colorful sky. The calm ocean reflects the golden light, with a sailboat visible in the distance and grasses framing the foreground.

4.68 out of 5 average rating, 165 reviews

Heart of Old Town Key West

5 out of 5 average rating, 10 reviews

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.

Flat in Marathon

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.

Flat in Marathon

4.62 out of 5 average rating, 1,328 reviews

Standard 1 Bedroom King Suite with Balcony

Private apartment rentals

A living area features a comfortable gray sofa adorned with several cushions, positioned between two side tables. A decorative mirror hangs above a console table, while light streams through glass doors leading to the patio. A textured area rug complements the tile flooring.

4.84 out of 5 average rating, 31 reviews

Sandbar Suite | 2 bed near Duval & waterfront

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

A modern kitchen and dining area feature light tile flooring and dark cabinetry. A dining table, surrounded by upholstered chairs, sits adjacent to a comfortable living space with a sofa and decorative pillows. Natural light fills the room from large windows, inviting a pleasant ambiance.

5 out of 5 average rating, 12 reviews

Key West at Hyatt Beach House

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, 314 reviews

#203 Key West Suites

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, 173 reviews

Duval Street Suites with full kitchen heated pool,

A bright living room features warm yellow walls and hardwood flooring. A light gray sofa with decorative cushions is positioned beside a coffee table. French doors lead to an outdoor space, while a ceiling fan adds comfort to the atmosphere.

4.66 out of 5 average rating, 32 reviews

Key West Garden - Green House

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.

4.82 out of 5 average rating, 262 reviews

#204 Key West Suites

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, 324 reviews

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

Apartment rentals with a hot tub

Fantasy Fest Huge 2 Story Townhouse Oldtown

An unobstructed view of the Atlantic Ocean is presented, featuring gentle waves and a sandy beach area. Lush palm trees frame the scene, while lounge chairs are arranged on a sun-drenched patio. Nearby, a set of white stairs leads to the beach, enhancing accessibility.

5 out of 5 average rating, 10 reviews

Key West ocean front Resort w/private sandy beach

5 out of 5 average rating, 4 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.

4.99 out of 5 average rating, 74 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

5 out of 5 average rating, 5 reviews

An inviting pool area is surrounded by palm trees and lounge chairs, creating a relaxed atmosphere. The spacious pool is illuminated by soft lights as twilight approaches, with a tiki bar nearby offering seating and scenic views of the tranquil waters.

Flat in Marathon

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.

4.89 out of 5 average rating, 9 reviews

Hyatt Windward Pointe! Great Location!

A modern kitchen is displayed, featuring dark blue cabinetry and stainless steel appliances. A sleek countertop hosts a sink and modern stove, while a microwave is mounted above. Natural light enters from a nearby window, enhancing the kitchen's functional layout.

5 out of 5 average rating, 3 reviews

Rare Beach Front Resort Key West- 2BD/2BA

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.