Apartment holiday rentals in Key West

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

Coral Palms 1BR/King/Queen, Pool, block to Duval

Escape to this charming 1BR, 2nd-floor condo in the heart of Historic Key West. Sleep soundly in a plush king bed and additional guests in a Queen & sofa bed in a spacious living area and a fully equipped kitchen. Lounge poolside under the palms, grill, or relax in the refreshing pool. No transportation needed, you're just steps from lively Duval Street, world-class dining, nightlife, and beaches. Perfect for a romantic getaway or a fun retreat, your island escape awaits! Hosted by Nautipussy!

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.

A Cuban Club Suite by Rent Key West Vacations

Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon became the center of social and community life for the Cuban population in Key West. After the original Cuban Club burned down in 1983, it was restored and converted to luxurious and spacious suites. The Cuban Club Suite stands as an award-winning historical landmark converted to a gorgeous two-bedroom suite filled with all the amenities needed for comfortable living.

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.

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.”

Exquisite Oceanfront Paradise - Key Colony Beach

Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #10 offers one king bed, a fully equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys sunset.

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.

Old Town Key West | Waterfront 2BR | Pool

Bring friends and family to this 1,350 sq ft waterfront corner condo in Downtown Key West. Just 1 mile to Duval Street, the Historic Seaport, and the Hemingway House—more space, more comfort, Key West done right. Enjoy a heated pool, tiki bar, BBQ grills, parking, building elevator, and secure keyless entry. Note: Dock access will be unavailable late April through May due to scheduled improvements; some daytime noise possible.

Orchid Bay Condo + Pool • Old Town • Walk to Duval

Stay in the heart of Old Town Key West—just 3 blocks from Duval—while enjoying a peaceful retreat with a pool and historic island charm. Start your mornings with coffee in a quiet tropical setting, then explore nearby shops, restaurants, and nightlife. After a day out, unwind by the pool or relax in your private suite. Perfect for couples or small groups who want to be close to everything without the noise.

Canal Front Luxury Condo | Pool + Breakfast

Welcome to THE MAD MAHI – your ultimate waterfront getaway! This stunning 1-bedroom condo (sleeps 4) in Marathon is the perfect spot for a relaxing retreat. Enjoy the season while relaxing with a full kitchen, private balcony, resort pool, Tiki Bar, restaurant, & Marina with boat ramp, trailer parking, boat and slips. Located between Key Largo & Key West, with shops and dining just a walk or bike ride away.

Affordable Beachfront Luxury Condo Sleeps 6

My place sits on Smather's beach! Close to downtown and the airport. You’ll love the condo because of the location, the large indoor space, it's quiet, the pool, and has all the comforts of home. My condo is good for couples, solo adventurers, business travelers, families (with kids), and big groups. It’s spacious - and very clean!