Apartment vacation rentals in Big Pine Key

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.

4.86 out of 5 average rating, 312 reviews

#201 Key West Suites

Welcome to your charming, private studio apartment located right on Duval Street! Originally built in 1919, this historic building was once known as the Central Hotel, reflecting its prime location at the heart of Duval Street at Southard. While this is a vacation rental rather than a traditional hotel (there is no lobby or on-site services), we’ve preserved the nostalgic character by naming it “Key West Suites Hotel” in honor of its rich history.

Apartment in Key Colony Beach

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.

4.86 out of 5 average rating, 143 reviews

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, 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.

4.92 out of 5 average rating, 265 reviews

Sunset Suite-Historic 2 BR, K/Q, Sleeps 4, Spa!

Historic 1880's Cigar Maker's cottage completely renovated. 1 K and 1 Q BR’s, half bath upstairs between BR’s, 32” Smart TV's, Full kitchen with granite counter tops, new stainless steel appliances. A newly remodeled bath with tumbled marbled tile, hairdryer. Also a totally private outdoor shower located in your private patio. All bath amenities provided, plus pool towels and daily housekeeping!

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, 105 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.

4.85 out of 5 average rating, 262 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.

4.92 out of 5 average rating, 173 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 Big Pine Key apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

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, 1,699 reviews

At Mine | Lovely Suite steps from Duval Street

A spacious living area features a light-toned sectional sofa arranged around a central coffee table. A large television is positioned on a wooden stand. Soft lighting is provided by lamps, and decorative artwork adorns the walls, enhancing the open and airy feel of the space.

4.76 out of 5 average rating, 54 reviews

Sombrero Beach 2 bedroom apartment close to Beach!

5 out of 5 average rating, 22 reviews

#1 Island Hideaway 89 - OCEAN FRONT

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.

4.77 out of 5 average rating, 285 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, 123 reviews

Sky Suite with Balcony Overlooking Duval Street

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

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, 9 reviews

Boot Key Harbor Penthouse

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.

4.84 out of 5 average rating, 57 reviews

"Hemingway" 1 bedroom at Leo's

Private apartment rentals

The exterior of the rental unit is showcased, featuring a vibrant yellow facade. A welcoming entrance is framed by lush greenery and palm trees, with a seating area that includes bright red chairs. The American flag is displayed proudly above the doorway.

4.93 out of 5 average rating, 95 reviews

Fully furnished Efficiency 50 yards from ocean, 10

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

A balcony is shown with a round glass table at the center, surrounded by four metal chairs. Lush greenery can be seen in the background, and sunlight casts gentle shadows on the floor. The view invites relaxation and outdoor dining.

4.55 out of 5 average rating, 42 reviews

Barracuda Bay Two Bedroom Condo

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, 877 reviews

Duval Balcony Spanky's Retreat

4.95 out of 5 average rating, 355 reviews

Honeymoon Hideaway, King bed, Private Deck & Spa!

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 waterfront view captures a serene canal lined with tropical greenery and residential boats. The white boat is positioned on the dock, with steps leading to an inviting home painted in a soft yellow. Clear blue skies enhance the tranquil atmosphere.

4.85 out of 5 average rating, 73 reviews

Little Venice in Marathon (in the Beautiful Keys)

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

4.93 out of 5 average rating, 14 reviews

Ibis Suite | Bright Hideaway, Hot Tubs, Near Duval

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, 75 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

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.

5 out of 5 average rating, 5 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.

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.