Apartment holiday rentals in Big Pine Key

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

Sombrero Beach Tropical Paradise Hotel

Spacious 1 Bedroom Condo at Skip Jacks Resort in the heart of Marathon, located at Mile Marker 50 Positions you in the perfect spot to explore all that the Florida Keys has to offer, Just 1 hour to Key West or Key Largo Spend your day,Boating,Snorkeling, Fishing, Lounging by the Pool or spend the Day at Sombrero Beach. The Condo has TV's with Wifi and a Fully Stocked Kitchen if you just want to Stay in sit on the Balcony and Enjoy the Music coming from the Live band at the Tiki bar VACA-24-205

Dock POOL Kayaks Bikes Beach2mi WalkToStores

Come enjoy tranquil Atlantic breezes at our DUPLEX. Enjoy all the keys islands & adventure in three (3) bedrooms & two (2) bathrooms with full tubs. Enjoy cooking & baking for family & friends On-site gated parking and dock space for ocean toys/ boat (35 ft max) on the 75 ft waterfront concrete seawall & wood dock complete with fish cleaning station and outdoor kitchen & grill to prepare your daily catches. Enjoy the multiple spacious outdoor spaces (shared) for playing, relaxing & dining.

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!

Ocean Isles Rustic Inn VACA-23-101

Escape to paradise in a brand new 1 bedroom/1.5 bathroom home, centrally located in Marathon, in Ocean Isles Fishing Village. Our condo is steps away from open ocean views with an enormous elevated pool overlooking the Atlantic. Condo is fully furnished will brand new amenities. Living room has a sleeper sofa with a queen memory foam mattress. Master bedroom has a king size memory foam cooling mattress, along with a twin trundle bed. Living and bedroom both equipped with 65" Smart Tvs.

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.

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.”

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.

#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"

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!

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.

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.