Condo vacation rentals in Big Pine Key

Villa 5027 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 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 and NO pets.

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.

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.

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.

Ocean Oasis!OceanView-Private Beach/Pool/TikiHuts

Welcome to Ocean Oasis, your tropical haven in Marathon, Florida! Our stunning 2-bedroom, 2-bathroom condo is located at 501 E Ocean Dr, Marathon, FL 33050. Ocean Oasis offers the ultimate beachfront retreat, with a King-sized bed in the master bedroom and two full-sized beds in the second bedroom, comfortably sleeping six. The spacious balcony boasts breathtaking views of the ocean and pool, perfect for sipping morning coffee or enjoying a sunset cocktail. No Pets Allowed.

"Abaco" Key West • 2/2 End Unit Waterfront+Dockage

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & building elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

Condo de Paradise/Salt Water Pool/Boat Dock

This is one of the best kept secret locations. Can be a very romantic escape. This is a good place for honeymooners, guys or gals getaway, fishermen/fisherwomen weekend get away or family time. A private unit in paradise in a gated community. Only 10 miles to Duval Street and all that Key West has to offer. There is a dock that can be used to dock up to a 26 foot boat that can be launched at Geiger Key, a mile down the road and they will store your trailer.

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.”

Keys Fall Escape: Pool, Marina & Tiki Bar

Celebrate the season in paradise at THE DAPPER DOLPHIN, an updated coastal-themed 1-bedroom, 1-bathroom condo, accommodating up to 4 guests. Featuring a complete kitchen, balcony, and access to 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!