Apartment vacation rentals in Stock Island

4.98 out of 5 average rating, 528 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 & BlueTooth stereo system with CD player & radio.

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

Welcome to Poseidon Too! A newly renovated 2/2 bath condo @ Sunrise Suites. Our condo is located 1 mile to the beach, 5 miles to downtown Duval St. With a full renovation just completed from top to bottom, you will enjoy top of the line furniture, furnishings, a brand new kitchen, and private balcony to enjoy amazing sunsets. Things To Note: - Guests will have full access to shared pool, hot tub, fitness room, & tennis court - Free parking - Keurig and drip coffee - Smart TV's in each room

A spacious bedroom features a large bed with a plaid blanket, accented by a collection of framed artwork on a bright blue wall. Wood flooring complements the overall decor, while a nearby closet provides convenient storage.

4.78 out of 5 average rating, 382 reviews

Key West - Sunrise ❀ The Green House

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.

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

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, 198 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, 451 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.

Apartment in Stock Island

A spacious living area displays a blue sectional sofa, accented with patterned throw pillows. A wooden coffee table is positioned in front, featuring a small potted plant and a woven basket. The open-concept kitchen is visible in the background, equipped with modern appliances.

4.9 out of 5 average rating, 73 reviews

"Key Lime" 1 bedroom at Leo's

Our "Key Lime" one-bedroom apartment located in Stock Island is the perfect place for your Key West getaway. Located only two blocks from the entrance to Key West, you can ride a bicycle, scooter, or golf cart to Key West from here. This unit is located inside Leo's RV park and you can enjoy the amenities we have in place during your stay including common area Tiki Huts, outdoor ping pong, chess, billiards, and the view of our lovely nature preserve.

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.

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, 156 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.

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.

4.85 out of 5 average rating, 251 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!

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.

4.91 out of 5 average rating, 150 reviews

Duval Street Suites with full kitchen heated pool,

Mile Zero Suite is a one bedroom (queen) 1 bath suite with a sleeper sofa (queen) and kitchen. Overlooking Duval street 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.

Popular amenities for Stock Island apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

A well-appointed bedroom features a spacious bed adorned with crisp white linens and blue accent pillows. The vibrant lime-patterned wallpaper creates a lively atmosphere. A mounted television is present, and natural light filters through two sets of blinds on the windows, offering a bright yet relaxing space.

4.9 out of 5 average rating, 126 reviews

Duval Street Suites full kitchen Old Town with hea

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, 290 reviews

#203 Key West Suites

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, 105 reviews

Duval Street Suites full kitchen and heated pool

4.95 out of 5 average rating, 20 reviews

Private room in Key West

Duval street downtown

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, 843 reviews

Duval Balcony Spanky's Retreat

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!

4.88 out of 5 average rating, 365 reviews

Private room in Key West

Mallory House Room #1

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, 760 reviews

Duval Balcony - Suite Mischief

Private apartment rentals

A well-lit bedroom features a spacious bed adorned with striped bedding and decorative pillows. A red dresser contrasts with the soft blue accent wall. Natural light floods in through windows, highlighting the warm wooden floor.

4.85 out of 5 average rating, 80 reviews

Lovely Apartment *Key West Best Locations *Sunset

The kitchen area features wooden cabinetry and a black refrigerator. A countertop holds a coffee maker, toaster, and various utensils. Natural light filters in through a nearby window, illuminating the tile backsplash and dual sink, providing a functional space for meal preparation.

4.87 out of 5 average rating, 68 reviews

King Bed | Key West *Best Downtown Locations (4)

The exterior of a multi-level villa is shown, featuring a light-colored façade with green shutters and a metal roof. Lush palm trees surround the building, offering a tropical ambiance, while a glimpse of the ocean is visible in the background against a serene sky.

5 out of 5 average rating, 3 reviews

Hyatt Windward Pointe! Great Location!

The living area features a light blue couch positioned near a brightly painted green wall, adorned with three framed artworks depicting ocean hues. A kitchen bar with a dark countertop highlights wooden cabinetry, while a woven rug adds texture to the bamboo flooring.

4.8 out of 5 average rating, 10 reviews

Key West Sunset | Apartment

A light-filled living space features a teal sleeper sofa and a small dining table with two white chairs. A textured area rug adds warmth to the wood floor. Decorative wall art and a ceiling fan enhance the relaxed atmosphere.

4.93 out of 5 average rating, 129 reviews

Duval Street Suites full kitchen, free parking, &

Apartment in Stock Island

A comfortable living area is displayed with a spacious sectional sofa, accented by a decorative pillow. A wooden coffee table, featuring a unique design, is positioned on a patterned rug. Natural light enters through a window dressed with simple blinds, illuminating the space.

4.79 out of 5 average rating, 38 reviews

"Hemingway" 1 bedroom at Leo's

A spacious living area features a blue sofa paired with a white coffee table. The kitchen bar, outfitted with black stools, complements the warm yellow walls and wooden cabinetry. Light floods through the windows with white blinds, enhancing the vibrant atmosphere.

5 out of 5 average rating, 6 reviews

Key West Garden - Green House

Apartment in Big Pine Key

A multi-colored building features a light teal exterior with white railings. The raised structure is supported by concrete pillars, with an outdoor space underneath that offers separation by white fences. A bright blue sky with scattered clouds is visible above.

5 out of 5 average rating, 15 reviews

New Deluxe Duplex Unit, 1 Queen Bed, Unit E-2

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!

New place to stay

The Grand Turk | Spectacular Sunset View, Private

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.

5 out of 5 average rating, 5 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.

4.88 out of 5 average rating, 8 reviews

Henry's Penthouse On The Ocean

The exterior of the resort is displayed along a waterfront, featuring a charming building with multiple balconies. Lush palm trees sway beside the property, and clear blue waters are visible in the marina, enhancing the relaxing coastal ambiance.

5 out of 5 average rating, 10 reviews

Downtown KeyWest 2Bed Oceanfront

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.