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Apartment vacation rentals in Big Pine Key

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Top-rated apartment rentals in Big Pine Key

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Two green chairs are positioned alongside a small round wooden table with a natural edge. A textured area rug covers the floor, while a gray sofa decorated with blue and white cushions completes the seating arrangement, creating a cozy living space.

Apartment in Tavernier

4.89 out of 5 average rating, 470 reviews

Capt Craigs Apartment

Capt. Craig’s Guest Quarters The Starfish is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer.

Top guest favorite

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.

Apartment in Key West

4.98 out of 5 average rating, 496 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 living area features a light green accent wall adorned with three framed blue art pieces. A light-colored sofa sits against the wall, complemented by a natural fiber rug on the bamboo flooring. A kitchen counter with a glossy black surface and wooden cabinetry is visible.

Apartment in Key West

4.84 out of 5 average rating, 104 reviews

The Green House ❀ Sunset

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 cozy living area is presented, featuring a gray sofa adorned with colorful cushions. A round wicker coffee table is centrally located, accompanied by two small wooden stools. A vibrant piece of wall art adds a pop of color, while light from a nearby lamp creates a warm glow.

Apartment in Tavernier

4.95 out of 5 average rating, 187 reviews

Capt Craigs Apartment

Capt. Craig’s Guest Quarters The Seahorse is a luxurious retreat located in Islamorada. Only 1 ½ hours from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From watersports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled with the traveler in mind, enjoy our little piece of paradise...minutes from all that the Upper Keys has. VR-012

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.

Apartment in Key West

4.92 out of 5 average rating, 184 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. Also there is discussion of spalling work in 2026 on balconies will firm dates as we get closer

A welcoming living room features two comfortable green sofas and a coffee table, set against large sliding glass doors that offer ocean views. Decorative lamps add a soft light, while a vibrant area rug enhances the space's warmth and connects with the outdoor scenery.

Apartment in Tavernier

4.83 out of 5 average rating, 259 reviews

Breathtaking Oceanfront Views at Tropical Daze

New Island Grill Pool Bar & Marina Cafe now open! Deluxe 2/2 right on the ocean, offering spectacular views of the purple and aquamarine waters of Tavernier Key. Jr Olympic Pool with hot tub. Resort community has a beach, iconic pier, marina, tennis & pickle ball. Gated entry with 24 hour security! Perfect location with popular waterfront restaurants, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

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.

Apartment in Key West

4.91 out of 5 average rating, 194 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.

Apartment in Marathon

4.97 out of 5 average rating, 103 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

The living area features a comfortable floral-patterned sofa positioned on a soft blue area rug. Light streams through windows adorned with white shutters, while framed palm tree artwork decorates the walls. A granite breakfast bar with three stools offers additional seating and connection to the kitchen.

Apartment in Key West

4.92 out of 5 average rating, 232 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!

The spacious studio apartment features a comfortable seating area with a leather sofa and armchair. Large windows allow natural light to enter, and the full kitchen with wooden cabinets is visible in the background. A dining area is positioned nearby, enhancing the open layout.

Apartment in Key West

4.85 out of 5 average rating, 270 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"

A historic conch home is showcased behind a vibrant green hedge and wooden gated entrance. The two-story structure features a light blue exterior with a spacious porch adorned with white railings, surrounded by lush tropical foliage.

Apartment in Key West

4.85 out of 5 average rating, 233 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!

Top guest favorite

An inviting living area is visible through open double doors. A spacious gray sofa and a wicker chair are arranged around a circular coffee table. A blue area rug adds a pop of color to the wood floor, with soft lighting illuminating the space.

Apartment in Key West

4.96 out of 5 average rating, 273 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).

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Villas

Luxurious estates for the ultimate escape

Popular amenities for Big Pine Key apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

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.

Apartment in Key West

4.88 out of 5 average rating, 49 reviews

Castaway Cove: Pet-friendly 2/2 condo near 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.

Apartment in Key Colony Beach

4.84 out of 5 average rating, 108 reviews

Beachside Unit 22 - Private Beach on Atlantic

A bright room features a casual seating area with a blue sofa and a patterned chair. A dining set with two chairs is positioned beside an open kitchen. The space is enhanced by a ceiling fan and showcases light-colored walls with natural light entering from a window.

Apartment in Key West

4.62 out of 5 average rating, 21 reviews

Shipyard 297-2 bed 2 bath condo in Truman Annex

A private balcony is furnished with a small round table and two chairs. Lush greenery surrounds the area, creating a serene environment. The white railing provides a classic touch, while the view includes tropical plants and glimpses of nearby buildings.

Apartment in Key West

4.83 out of 5 average rating, 6 reviews

Sailfish Suite on Duval

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.

Apartment in Key West

4.9 out of 5 average rating, 115 reviews

Duval Street Suites with full kitchen heated pool,

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.

Apartment in Key West

4.68 out of 5 average rating, 50 reviews

Charming 1BR two-story apartment with 2 balconies

A cozy living area is presented with wooden walls and hardwood floors. Seating includes a comfortable couch adorned with a colorful throw and two blue chairs. A wooden coffee table sits in the center, complemented by a large lamp providing warm light. A television is positioned on a wooden console.

Apartment in Key West

5 out of 5 average rating, 11 reviews

Key West Garden Oasis, Best location!

A comfortable living area is furnished with a tropical-patterned couch, accompanied by a vibrant red coffee table. Decorative artworks adorn the walls, and natural light illuminates the space. A dining area with a wooden table can be seen in the background, while a staircase leads to the upper level.

Apartment in Key West

4.92 out of 5 average rating, 12 reviews

Key West Casa by AvantStay | Week-Long Stays

Private 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.

Apartment in Marathon

5 out of 5 average rating, 13 reviews

"O" Fish Ally Paradise @Ocean Isle Fishing Village

An outdoor shower is positioned beside a vibrant mosaic wall, with water cascading down in front of a swimming pool area. Lounge chairs in shades of blue and green surround the pool, complementing the tropical foliage visible in the background.

Apartment in Tavernier

5 out of 5 average rating, 3 reviews

Superb Ocean View w/heated pool, beach, tennis

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

4.77 out of 5 average rating, 39 reviews

Poolside 2 queen Apartment

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.

Apartment in Marathon

4.92 out of 5 average rating, 13 reviews

Relax with the whole family at this peaceful place

A bright living area features a comfortable turquoise sofa and an armchair with tropical patterns. A wooden coffee table is centered in the space. A wall-mounted television provides entertainment options. Light spills in from glass doors leading to an outdoor balcony with views of palm trees.

Apartment in Key West

4.86 out of 5 average rating, 7 reviews

Coconut Mallory 2 Bedroom w/ Pool 114

An aerial view captures a coastal area featuring a hotel building alongside a waterway. A sandy beach area with lounge chairs is visible near the water, while lush greenery surrounds the landscape. The scene showcases a calm and inviting atmosphere with clear blue skies.

Apartment in Tavernier

5 out of 5 average rating, 6 reviews

Panoramic Ocean Views, Ocean Pointe Condo

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.

Apartment in Key West

4.83 out of 5 average rating, 23 reviews

Apartment at Safe Harbor Marina

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.

Apartment in Marathon

5 out of 5 average rating, 5 reviews

Boot Key Harbor Penthouse

Apartment rentals with a hot tub

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.

Apartment in Key West

5 out of 5 average rating, 7 reviews

Partial ocean view studio with king bed

Top guest favorite

A tranquil beach scene is depicted with clear blue skies and gently swaying palm trees. Soft sand lines the shore, while calm waters reflect the greenery of surrounding mangroves. Beach loungers are positioned on the sand, inviting relaxation amidst a natural landscape.

Apartment in Tavernier

4.97 out of 5 average rating, 86 reviews

Turtles Nest 2 Ocean Point condo

Top guest favorite

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.

Apartment in Key West

5 out of 5 average rating, 40 reviews

Newly Renovated 2/2 Bath Condo, with shared pool

A bright living area features a comfortable gray sofa, decorative chairs, and a coffee table on a patterned rug. Natural light floods the space through large windows, creating a relaxed atmosphere. A wall-mounted TV and a small desk can also be seen, along with coastal decor.

Apartment in Tavernier

5 out of 5 average rating, 45 reviews

When Paradise is Key: Tropical Oceanfront Condo

A modern living area features a clear glass coffee table supported by natural wood elements. Two light-toned armchairs complement a textured area rug, while a media console displays decorative accents. A sliding glass door allows natural light in, alongside minimalistic wall décor.

Apartment in Tavernier

4.67 out of 5 average rating, 3 reviews

Seaside Serenity Brand New Remodeled 2 Bed 2 Bath

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.

Apartment in Key West

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.

Apartment in Key West

4.75 out of 5 average rating, 4 reviews

The Samana Cay | Tropical, Airy Retreat w/ Private

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.

Apartment in Key West

5 out of 5 average rating, 4 reviews

Henry's Penthouse On The Ocean

Quick stats about apartment rentals in Big Pine Key

Total rentals
10 properties
Nightly prices starting at
G$10,449 GYD before taxes and fees
Total number of reviews
460 reviews
Wifi availability
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
Local attractions
No Name Pub, Kiki's Sandbar Bar & Grille, and Big Pine Rooster

Destinations to explore