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Apartment holiday rentals in Big Pine Key

Find and book unique apartments on Airbnb

Top-rated apartment rentals in Big Pine Key

Guests agree: these apartments are highly rated for location, cleanliness and more.

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Top guest favourite
A private hot jacuzzi is nestled under a sheltered area, surrounded by green foliage. Soft seating is positioned nearby, and natural light filters through the striped curtains. A staircase in the background leads to an upper level, while a wooden fence offers privacy.
Apartment in Key West
4.94 out of 5 average rating, 103 reviews

Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our unique and charming Airbnb. This cozy retreat offers the perfect blend of comfort and style, featuring a private porch where you can relax and enjoy the island breeze. Take a dip in the refreshing pool or unwind in the private hot jacuzzi after a day of exploring. Enjoy cooking a delicious meal on the grill, and experience a peaceful stay in a one-of-a-kind space. Whether you're here to relax or explore, our home provides everything you need for an unforgettable Key West getaway!

Guest favourite
A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.
Apartment in Key West
4.95 out of 5 average rating, 197 reviews

Fully renovated 2/2 bath condo w/ shared pool!

**Brand New Listing** Welcome to Captains Choice - The NICEST Unit at Sunrise Suites Key West, unit 302. Tropical winds, sunset views and Key West charm await when you book your stay in this gorgeous completely renovated two bedroom, two bathroom condo "Captain's Choice". Highlights include: Smart TVs in each room Keurig New stainless Kitchen/appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, & Smathers Beach End unit One parking space, free of charge

Guest favourite
The image captures a serene view of the Atlantic Ocean, featuring varying shades of blue and green water. A sandy beach is visible in the foreground, along with lounge chairs arranged on a patio. Lush palm trees frame the scene, adding to the tropical ambiance.
Apartment in Key West
4.9 out of 5 average rating, 102 reviews

Ocean Front Studio private Sandy Beach in Key West

Studio unit with fridge, microwave, settings for 2 and a king sized bed. Doors that open to a balcony overlooking the Atlantic Ocean. There is pool, hot tub, and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street. The resort is located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. There is free garage parking with the room. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy air conditioning.

Top guest favourite
Apartment in Marathon
4.97 out of 5 average rating, 117 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

7 DAY MINIMUM BOOKINGS / MAX 4 PERSONS NAUTI HIDEAWAY - This Nauti Stays Vacation Rental property is a 2-bedroom, 2-bath 2nd level 925 sq ft. condo located in Coco Plum, Marathon. Set in a well-protected, deep canal on the Atlantic, comes with a deep slip (length up to 40 ft) next to pool allowing access to the Atlantic Ocean and Florida Bay. ONSITE boat ramp & trailer (36 ft max) parking! Enjoy a heated or chilled pool after a boat day! Dock has water, power hook ups & fish cleaning station.

Top guest favourite
A private balcony overlooks calm waters with a soft sunrise reflecting on the surface. Green mangroves frame the view, while white columns and railing enhance the serene atmosphere. The balcony is furnished with a chair, inviting relaxation while enjoying the scenic vista.
Apartment in Key West
4.98 out of 5 average rating, 133 reviews

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

Guest favourite
An outdoor deck features a wooden table surrounded by a mix of chairs, including colorful green and brown options. Lush palm trees and vibrant landscaping fill the view, creating a tranquil atmosphere ideal for relaxation.
Apartment in Duck Key
4.87 out of 5 average rating, 109 reviews

Villa 5087 on Duck Key BOAT SLIP available

Enjoy a Fully Renovated Villa on Duck Key. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors, NO pets. Please do not take any items from the Villa. No pool access

Top guest favourite
Apartment in Key West
4.89 out of 5 average rating, 135 reviews

Waterfront Condo Dock Pool Near Duval St

Relax above it all in this spacious top-floor waterfront condo in downtown Key West, offering added privacy and sweeping marina views. Perfect for families and groups, enjoy a full kitchen, open living space, and private balcony. Dockage available with a fish cleaning station and ice maker, ideal for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and 10 minutes from EYW airport, with a heated pool, tiki area, BBQ grills, parking, and secure entry.

Guest favourite
The resort-style pool is surrounded by lush tropical landscaping, featuring palm trees and colorful plants. Lounge chairs are positioned near the pool's edge, reflecting in the calm water. Clear blue skies enhance the tranquil ambiance of this inviting outdoor space.
Apartment in Summerland Key
4.97 out of 5 average rating, 30 reviews

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Superhost
Apartment in Marathon
4.93 out of 5 average rating, 114 reviews

Waterfront Luxury Condo | Pool + Tiki Bar

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and resort amenities including a pool, Tiki Bar, restaurant, Marina, and more. Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

Guest favourite
A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.
Apartment in Key West
4.89 out of 5 average rating, 290 reviews

Tropical Old Town Bungalow

Great Location, Close to Duval & Beach Welcome to paradise! This Tropical Old Town Bungalow is located perfectly between Key West’s best beaches and the best restaurants and nightlife! The rental unit sits right between the White Street Art Gallery District and the Historic District, which features some of Key West’s most historic homes and properties. Whether you are walking, riding bikes or grabbing a quick cab, no destination is too far from this conveniently located rental.

Guest favourite
A clear pool glimmers under the sun, surrounded by palm trees. Lounge chairs are positioned by the poolside, while tiki huts can be seen in the distance. The condominium buildings frame the view, creating a peaceful outdoor space.
Apartment in Key Colony Beach
4.88 out of 5 average rating, 156 reviews

Beachside Unit 33-Private Tropical Beach Plus Pool

Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and 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.”

Guest favourite
A modern kitchen is showcased, featuring stainless steel appliances, including a microwave, oven, and refrigerator. Sleek white cabinetry complements the light-colored countertops. A view into the adjoining space is visible, hinting at a well-lit dining area.
Apartment in Key West
4.9 out of 5 average rating, 174 reviews

Tropical Escape at Sunrise

We thoroughly sanitize upon check-out. This luxurious condo features a wonderful tropical interior design. It includes 2 spacious BR's: king bed/ full bath, queen bed/ full bath). Our living room sofa bed accommodates 1 guest. A fully equipped kitchen. Patio overlooks pool. WiFi, basic cable, 3 TV's, A/C, washer-dryer, workout center, BBQ, tennis court, elevator, parking. Accommodates no more than 5 guests. Must be 25 and older.

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