Apartment holiday rentals in Stock Island

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, 144 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.

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.

4.85 out of 5 average rating, 59 reviews

"Hemingway" 1 bedroom at Leo's

Our Hemingway” 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 easily ride a bicycle, scooter, or golf cart into town. This unit is located inside Leo’s RV Park, where guests can enjoy shared amenities including common-area tiki huts, outdoor ping pong, chess, billiards, and beautiful views of our nature preserve. For the comfort of all guests, pets are not allowed in this unit.

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, 473 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.

5 out of 5 average rating, 15 reviews

Key West Beach House

Welcome to the Hyatt Beach House, a Hyatt Residence Club, your own private sanctuary in Key West with crystal-clear water views and direct beach access. Enjoy the private beach, furnished with thick-cushioned chairs, picnic tables, barbeque grills and a private dock. Soak up the sun in the zero-entry lagoon shaped pool and hot tub. Walk down stairs and enjoy the complimentary kayaking, gorgeous beach area and pool. Spend a wonderful week in the sunny Florida Keys!

4.98 out of 5 average rating, 556 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.

4.92 out of 5 average rating, 326 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 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, 106 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.

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, 200 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.

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, 263 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!

4.92 out of 5 average rating, 120 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, 165 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 Stock Island apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

5 out of 5 average rating, 3 reviews

Cayo-Hueso Suite | Chic 1BR + Balcony in

4.96 out of 5 average rating, 27 reviews

Casa Caribe 2bed2bath sleeps 6 beautiful decorated

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.

4.86 out of 5 average rating, 1,711 reviews

At Mine | Lovely Suite steps from Duval Street

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.

4.86 out of 5 average rating, 50 reviews

Duval Corner - Pet friendly with Balcony

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.

4.88 out of 5 average rating, 88 reviews

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

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.

4.76 out of 5 average rating, 288 reviews

Old Town Suites - 2 Bedroom Suite #2

A spacious common area features high ceilings and large windows allowing natural light to fill the room. A wooden dining table seats six, complemented by light blue chairs. A plush sofa is arranged with textured cushions. French doors open to the balcony, enhancing the indoor-outdoor connection.

4.84 out of 5 average rating, 125 reviews

Sky Suite with Balcony Overlooking Duval Street

A charming cottage exterior features a bright red door framed by white railings. American and local flags adorn the entrance, while tropical foliage is visible in the foreground. The house displays classic architectural details with light blue trim and a detailed gable.

4.63 out of 5 average rating, 97 reviews

Porchside Paradise @ Conch Republic Cottages

Private apartment rentals

4.56 out of 5 average rating, 9 reviews

Key West Condo 2nd Floor 2BDR beach, pool, balcony

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, 883 reviews

Duval Balcony Spanky's Retreat

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, 19 reviews

Coconut Mallory Studio-401

4.94 out of 5 average rating, 357 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

4.88 out of 5 average rating, 65 reviews

1BR with balcony & lighthouse view, steps to Duval

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, 264 reviews

#204 Key West Suites

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, 795 reviews

Duval Balcony - Suite Mischief

4.82 out of 5 average rating, 11 reviews

Beautiful Getaway in the Heart of Key West

Apartment rentals with a hot tub

Fantasy Fest Huge 2 Story Townhouse Oldtown

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

The suite features two Queen beds placed against a blue accent wall. A small dining table occupies one corner, complemented by wooden chairs. Natural light fills the room through a nearby window, while terracotta tiles provide a warm, inviting atmosphere.

4.8 out of 5 average rating, 15 reviews

Pelican Suite | Cozy Cottage, Hot Tubs, Close to D

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.

4.82 out of 5 average rating, 11 reviews

Hyatt Windward Pointe! Great Location!

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, 77 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.

Apartment in Marathon

Marathon Studio on Lovely Gulf Front Resort

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 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.