Apartment holiday rentals in Big Pine Key

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Top-rated apartment rentals in Big Pine Key

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Guest favourite
Flat in Marathon
5 out of 5 average rating, 7 reviews

Villa 4204 on Duck Key - Boat Slip available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This apartment boasts breathtaking sunsets, close to water sports, 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

Top guest favourite
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.
Flat in Key West
4.95 out of 5 average rating, 465 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.

Guest favourite
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.
Flat in Marathon
4.87 out of 5 average rating, 113 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.

Guest favourite
Flat in Key West
5 out of 5 average rating, 8 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 !

Top guest favourite
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.
Flat in Key Colony Beach
4.86 out of 5 average rating, 136 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.”

Top guest favourite
Flat in Key West
4.98 out of 5 average rating, 542 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.

Guest favourite
Flat in Key West
4.92 out of 5 average rating, 257 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!

Superhost
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.
Flat in Key West
4.85 out of 5 average rating, 302 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"

Superhost
Flat in Marathon
5 out of 5 average rating, 3 reviews

Complimentary Breakfast & Daily Housekeeping!

The Moonlit Manatee, a fresh waterfront villa in Marathon, FL, made for easygoing Keys escapes. This 1BR/1BA villa sleeps 4 and features a king bedroom, spa-inspired bath, inviting living space with sleeper sofa, and a fully stocked kitchen. Enjoy coffee on your private patio with marina views, or keep your boat at your slip and settle into island time.

Guest favourite
A cozy bedroom features a spacious bed dressed in white linens and decorative pillows. Natural light filters through a window adorned with wooden blinds. A mirror and wicker accents complement the tropical wall decor, while dark hardwood flooring adds warmth to the space.
Flat in Key West
4.96 out of 5 average rating, 126 reviews

Duval Street Suites full kitchen, free parking, he

Paradise 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.

Guest favourite
A shared pool area is showcased overlooking Garrison Bight Marina. Lounge chairs are arranged around the pool, with a thatched gazebo providing shaded seating. The marina is visible in the background, featuring moored boats and palm trees against a clear sky.
Flat in Key West
4.92 out of 5 average rating, 106 reviews

Waterfront Condo FREE Slip & Pool 2B2B in Key West

🌴 Key West Waterfront Paradise – FREE Dockage Included! Wake up to breathtaking marina views, unwind in the heated pool, and walk or bike to Duval Street in minutes. Enjoy a spacious condo with a private balcony, exclusive boat slip, and all the comforts you need for an unforgettable stay in the heart of Key West.

Top guest favourite
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.
Flat in Key West
4.91 out of 5 average rating, 163 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

Popular amenities for Big Pine Key apartment rentals

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Quick stats about flat rentals in Big Pine Key

  • Total holiday rentals

    Explore 10 holiday rentals in Big Pine Key

  • Nightly prices starting at

    Big Pine Key holiday rentals start at £45 per night before taxes and fees

  • Verified guest reviews

    Over 540 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Wifi availability

    10 of Big Pine Key holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Big Pine Key rentals

  • 4.7 Average rating

    Big Pine Key stays receive an average rating of 4.7 out of 5 from guests

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