Condo holiday rentals in Stock Island

Sky Loft - Steps from Duval Street & Shared Pool

Experience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duval Street, this top-floor gem puts you right at the heart of the action. From vibrant bars and restaurants to must-see local attractions, adventure is just steps away. Unwind by the inviting pool, complete with cozy lounge chairs, and soak in the island vibes. Bright, airy, and perfectly located, Sky Loft offers incredible value for couples or friends looking to enjoy the ultimate Key

Family · Location · Outdoor spaces

Waterfront Condo Dock Pool Downtown Near Duval

Time to relax and vacation in this spacious 1,350 sq ft waterfront corner condo in downtown Key West. Bring your family and friends and enjoy a private balcony with marina views, full kitchen, and open living space. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Amenities include a heated pool, tiki area, BBQ grills, free parking, elevator access, and secure entry. Located about 1 mile from Duval Street and 10 minutes from EYW airport.

Location · Family · Barbecue

Resort Escape | Pool+Hot Tub | Sleeps 6

Escape to Key Lime Paradise, a bright, modern 2bed, 2-bath, Sleeps 6, (queen size sofa bed ) condo in Key West. Perfect for couples or families, it features a private balcony, a fully equipped kitchen, and a dedicated workspace. Enjoy resort-style amenities, a pool, hot tub, gym, and tennis court. Just a short drive from the vibrant energy of Duval Street, this peaceful retreat offers the best of both worlds. Two elevators serve the building, providing quick and convenient access to the condo.

Family · Value · Hospitality

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.

Value · Location · Kitchen

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 & drip coffee New stainless appliances In-unit, full size washer/dryer Located near restaurants, a convenience store, Beach, beach towels One parking space, no charge

Value · Location · Quiet

Charming Key West By the Sea

Home of Famous Ernest Hemingway and Jimmy Buffet. Enjoy the downtown area on Duval Street where Sloppy Joe's and Captain Tony's bar are located. .Hemingway House greets thousands of visitors to experience the 6 toe cats living on the property. The Ole Light House Museum across the street is a highlight. A tropical boater's and angler's paradise boasts the best fishing and weather in the country. With tangerine sunsets glistening across the calm Atlantic and Gulf of America.

Family · Location · Nearby

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.

Location · Family · Pool

Tropical Heron Hideaway w/ Hot Tub + Pool

Welcome to our charming 1932 Key West retreat in the peaceful Meadows neighborhood. This unique getaway features a private porch, a private hot tub, access to a shared pool and BBQ grill, and all the comforts of home. Blending historic island charm with modern amenities, it’s just minutes from Duval Street, the Historic Seaport, beaches, restaurants, and local attractions—the perfect place to relax and experience authentic Key West.

Value · Location · Checkout

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.

Value · Family · Getting around

EYW Getaway

Relax with the whole family at this peaceful place to stay. Our two-bedroom two-bathroom condo with complete kitchen is located at Sunrise Suites Resort. Amenities include shared heated pool, hot tub, tennis court and a basic gym. Our condo is located 1mile from the airport, 1.5 miles from the beach and 3.5 miles from downtown Duval St.

Family · Location · Checkout

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!

Value · Family · Amenities

Moonlight Paradise Upgraded Family oasis Tropical

Moonlight is a totally renovated condo that is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own private balcony. Beautiful tropical decor. No attention to detail has been spared. Stainless Appliances & luxurious finishes.

Family · Location · Getting around