Apartment vacation rentals in Stock Island

A bright and welcoming living space features a galley kitchen with a counter and two stools. The refrigerator is visible along with colorful walls in shades of yellow and coral. A TV unit stands nearby, and a red sofa adds a pop of color to the cozy area.

4.98 out of 5 average rating, 520 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 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, 337 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

This Historic unit has Pale blue interiors, small efficiency kitchen, platform Pottery Barn King 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. Bose 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!

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, 291 reviews

Sunrise - Best Downtown Locations

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.

4.86 out of 5 average rating, 102 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, 194 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 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, 35 reviews

Apartment at Safe Harbor Marina

Take it easy at this unique and tranquil getaway. Enjoy Waterfront Views on both sides, boat docks right outside front door, Hogfish restaurant right next door and 4 Miles to Downtown Key West. If you’d like any activities or equipment rentals please reach out to Shon the property manager and checkout his website “Fun In The Sun Key West”. Boat rentals & charters, golf carts, dry tortugas charters, and more. When checking in be sure to follow the arrival guide! Thanks!

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.

5 out of 5 average rating, 3 reviews

Oceanview condo w/pool, jacuzzi

Plan your next vacation at this peaceful, breathtaking, Ocean-view condo at La Brisa resort located across the street from largest beach on the island, Smathers Beach. Take advantage of the pool, tennis courts, hot tub, and sauna or just enjoy the Atlantic Ocean view from your private balcony. The condo is in a gated community with private parking and elevator access. Bring your family and lets enjoy your vacation in Key West 🌴☀️ No pets allowed !

A well-lit bedroom features a queen-sized bed with white linens and a wooden frame. A lay flat couch is situated against the wall. Two bedside lamps and a wooden dresser with rattan detail enhance the space. An air conditioning unit is visible on the window.

4.91 out of 5 average rating, 217 reviews

Duval St Apartment w/ Balcony w/parking Adult Only

This large apartment overlooks Duval Street from a private balcony. Perfect location in the heart of Old Town within easy walking distance of restaurants, live music, and historic sites. Guests enjoy daily complimentary continental breakfast in the garden and dips in our heated pool. *Please note you must be 21 or older to make a reservation on this property and all guests must be at least 18 years old.*

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.

4.9 out of 5 average rating, 152 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, 154 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.

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, 288 reviews

#201 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 bordering Southard Street and is on 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"

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, 245 reviews

Studio Near Downtown - The Bartlum

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!

Popular amenities for Stock Island apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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, 377 reviews

Key West - Sunrise ❀ The Green House

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.

4.84 out of 5 average rating, 825 reviews

Duval Balcony - Street Suite

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, 141 reviews

Duval Street Suites with full kitchen heated pool,

4.94 out of 5 average rating, 17 reviews

Private room in Key West

Duval street downtown

A cozy living area is adorned with a teal sofa and a circular side table. A vibrant area rug anchors the space, while large glass doors lead to a balcony, offering views of the outdoors. Natural light fills the room through multiple windows.

4.67 out of 5 average rating, 67 reviews

Charming 1BR two-story apartment with 2 balconies

A light-filled living area features a comfortable gray sofa and two accent chairs, arranged around a coffee table. A media console with a television is placed against the wall. Large sliding glass doors lead to a private screened-in porch, with views of palm trees.

4.67 out of 5 average rating, 3 reviews

Welcome to Your Tropical Key West Island Getaway

4.88 out of 5 average rating, 361 reviews

Private room in Key West

Mallory House Room #1

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, 296 reviews

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

Private apartment rentals

Apartment in Big Pine Key

A modern kitchen features white cabinetry and a granite countertop. Stainless steel appliances, including a refrigerator and oven, are present. A coffee maker and additional kitchen equipment are visible on the counter. Soft grey curtains adorn the window, allowing natural light to enter.

4.95 out of 5 average rating, 41 reviews

New Deluxe Duplex Unit, 2 Queen Beds, Unit H-5

The suite interior features a spacious king bed against a light-colored wall, complemented by a large flat screen TV mounted opposite a cozy seating area. A black sofa with plush white cushions is positioned nearby, and a kitchenette is visible in the background.

4.83 out of 5 average rating, 23 reviews

Honeymoon Banyan Suite near Higgs Beach

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.

4.88 out of 5 average rating, 74 reviews

Lovely Apartment *Key West Best Locations *Sunset

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.

4.91 out of 5 average rating, 70 reviews

"Key Lime" 1 bedroom at Leo's

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, 119 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, 285 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.

4.92 out of 5 average rating, 97 reviews

Duval Street Suites full kitchen and heated pool

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, 241 reviews

#204 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.

4.91 out of 5 average rating, 82 reviews

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

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, 54 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

A charming entrance is framed by lush tropical plants and palm trees. The light green door complements the inviting beige exterior of the home. A cozy seating area is situated on the porch, and brick pathways lead through a landscaped yard filled with vibrant foliage.

4.93 out of 5 average rating, 46 reviews

Heron Hideaway

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!

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 bright living area features a coral-colored sofa, rattan seating, and a flat-screen TV. Natural light floods the space through large sliding glass doors leading to a private balcony with outdoor seating. The adjoining bedroom is visible through an open doorway.

4.89 out of 5 average rating, 9 reviews

The Samana Cay | Tropical, Airy Retreat w/ Private

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.