Apartment vacation rentals in Big Pine Key

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.

4.77 out of 5 average rating, 363 reviews

Key West - Sunrise ❀ The Green House

Unique and beautifully renewed apartment in the heart of Key West. Spacious bedroom with King Size bed and Walk-in Closet, large living room with pull-out sofa bed and kitchen. Take advantage of our unbeatable price and enjoy! ♡ Best location for exploring Key West, in the epicenter of Old-Town and all attractions. One corner from world-famous Sloppy Joe's (Hemingway's favorite place) and Duval Loop, the free local ride. Check out the map and see all attractions right around The Green House!

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, 505 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, 319 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 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.

4.91 out of 5 average rating, 186 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 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.

4.88 out of 5 average rating, 1,504 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. Located on a quiet street, it offers a private pool and peaceful stay for vacationers and business travelers. The unit includes a comfy Queen bed, mini fridge, microwave, iron & board, hangers, TV, and AC. Enjoy Key West's warm weather year-round. This special place is close to everything, making it easy to plan your trip. Just a heads-up: Key West’s famous roosters love to strut and crow—part of the island charm!

A welcoming entrance features a door labeled '8A' and is flanked by two red chairs with blue and white striped cushions. A small table rests between them, surrounded by potted plants. A window offers a glimpse of natural light within the unit.

4.86 out of 5 average rating, 107 reviews

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat sofa and a small dining table with 2 chairs. Private bathroom. AC will keep you cool. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Optional boat slip can be rented for $25/night Efficiency has a 2 person maximum occupancy - no exceptions.

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.

4.84 out of 5 average rating, 115 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.”

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.

4.9 out of 5 average rating, 201 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.*

A light-filled living room features a blue sofa, a comfortable chair, and a glass coffee table. Large sliding doors open to a balcony with ocean views. A soft area rug lies on the tiled floor, adding warmth to the space, while sunlight illuminates the room.

4.97 out of 5 average rating, 105 reviews

Beachfront Condo w/ Ocean Views in Marathon

Beautifully decorated 2nd floor end unit with stunning panoramic ocean views from the balcony, living room and master bedroom. Two bedrooms / two full bathrooms and washer and drier in unit. Full kitchen. Directly on the beach! Beach chairs, umbrellas and towels provided for you. Guests have access to the heated swimming pool, tennis court and beach. Master bedroom king-size memory foam mattress

A cozy living area features a sectional sofa in a muted tone, paired with a wicker chair. A round coffee table sits in the center, with light blue area rug beneath. Large windows provide views of an outdoor space while allowing natural light to fill the room.

4.96 out of 5 average rating, 280 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

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, 116 reviews

Duval Street Suites full kitchen, free parking, &

The Key West Suite is a one bedroom (king) 1 bath suite with a sleeper sofa (queen) and kitchen. 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.

Apartment in Big Pine Key

A modern kitchen is equipped with stainless steel appliances, including a refrigerator, stove, and microwave. Light-colored cabinetry contrasts with the granite countertops, while a window adorned with patterned curtains allows natural light to brighten the space.

4.87 out of 5 average rating, 70 reviews

New Deluxe Duplex Unit, 1 Queen Bed, Unit C

This is a Brand New One Bedroom Duplex unit with central AC, Dishwasher, garbage Disposal, etc. This unit has a queen bed in the bedroom, and a queen sofa sleeper in the living room. It is elevated and has absolutely Gorgeous views of Old Wooden Bridge Marina. All furnishings are brand new. This property is not pet friendly.

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Popular amenities for Big Pine Key apartment rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

The image presents a view from a balcony overlooking the tranquil ocean. Palm trees line the property, and the aquamarine water can be seen in the distance. Nearby, a well-maintained path separates the buildings from the fishing dock.

5 out of 5 average rating, 15 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

A large swimming pool is surrounded by palm trees and lounge chairs. Umbrellas and shaded areas are present for guest comfort. The area is illuminated in a blue evening light, with a relaxed atmosphere enhanced by nearby dining options.

4.56 out of 5 average rating, 64 reviews

Accessible Deluxe 1 Bedroom King Suite w/ Balcony

A well-lit bedroom features two spacious beds with white bedding, positioned beside a nightstand with a lamp. A large window offers natural light, complemented by green walls. A closet and a dresser are visible in the background, enhancing the room's functionality.

Apartment in Islamorada

4.78 out of 5 average rating, 46 reviews

Poolside 2 queen Apartment

A private patio features a heated dipping pool surrounded by lush greenery. Comfortable lounge chairs and a shaded seating area are arranged on an elegant wooden deck. The distinctive red brick wall of the house adds character to the serene outdoor space.

4.73 out of 5 average rating, 37 reviews

Red Room at the Grand Maloney

A spacious living area is presented, featuring a comfortable sectional sofa adorned with decorative pillows. A light-colored coffee table sits in front, complemented by a small plant. Large sliding glass doors allow natural light and provide views of the outdoor space.

4.94 out of 5 average rating, 16 reviews

Relax with the whole family at this peaceful place

The living area features a colorful floral sofa and a vibrant orange coffee table. A ceiling fan provides airflow, while a blue accent chair adds comfort. The dining area is visible in the background with a table set for four, and a staircase leads to the upper level.

4.92 out of 5 average rating, 12 reviews

Key West Casa by AvantStay | Week-Long Stays

The open living space features a cozy couch and vibrant armchair, with a seating area seamlessly connected to the kitchen and dining space. Large glass doors offer a view of the balcony and serene harbor, allowing natural light to brighten the room.

5 out of 5 average rating, 6 reviews

Boot Key Harbor Penthouse

A sandy beach area extends towards calm blue waters, featuring lounge chairs positioned for relaxation. A private dock is visible, alongside the jetty, leading into the water. Lush greenery surrounds the space, enhancing the tranquil coastal setting.

Apartment in Islamorada

4.88 out of 5 average rating, 51 reviews

Endless Bay Views, Sues Promise Islamorada FL

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Private apartment rentals

A serene bedroom is adorned with a blue and white palm leaf wallpaper, featuring a spacious bed dressed in a deep blue quilt. Two bedside lamps provide soft lighting, and a colorful decorative pillow adds contrast. A framed artwork depicts a bird against the wall.

4.89 out of 5 average rating, 109 reviews

Duval Street Suites full kitchen Old Town with hea

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, 127 reviews

Duval Street Suites with full kitchen heated pool,

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.

5 out of 5 average rating, 9 reviews

Duval Corner - Pet friendly with Balcony

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.

4.63 out of 5 average rating, 60 reviews

Charming 1BR two-story apartment with 2 balconies

The outdoor area features a charming pool surrounded by lush tropical landscaping and palm trees. A view of the two-story home is visible in the background, showcasing its inviting exterior. Several loungers are strategically placed beside the pool, offering a relaxing space.

5 out of 5 average rating, 16 reviews

Horse Conch~ Amazing Location With Shared Pool

Apartment in Big Pine Key

A two-story building with a bright green exterior is shown, featuring elevated construction on concrete pillars. The front porch is lined with white railings, and the entrance includes double doors. Nearby, a paver driveway leads to a boat, adding functional appeal to the setting.

4.82 out of 5 average rating, 17 reviews

New Deluxe Duplex Unit, 2 Queen Beds, Unit I-6

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.

4.86 out of 5 average rating, 29 reviews

Apartment at Safe Harbor Marina

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, 279 reviews

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

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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, 56 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.

5 out of 5 average rating, 43 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

A waterfront view showcases a multi-story building surrounded by palm trees, with balconies overlooking the marina. The clear blue water is visible in the foreground, bordered by a wooden dock, providing access to several boats moored at the slips.

4.25 out of 5 average rating, 4 reviews

Downtown Sunset Harbor Studio!

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.

5 out of 5 average rating, 14 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, 4 reviews

Hyatt Windward Pointe! Great Location!

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.

4.86 out of 5 average rating, 7 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.