Condo holiday rentals in Key West

A modern living area features a spacious layout with a comfortable seating arrangement and a large flat-screen TV mounted on the light green wall. Natural light floods in through expansive glass doors, revealing views of the outdoors. A stylish kitchen island with sleek countertops complements the space.

4.95 out of 5 average rating, 166 reviews

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

Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.

5 out of 5 average rating, 101 reviews

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.

Condo in Key Colony Beach

A spacious studio features a comfortable bed dressed in soft blue and white linens, complemented by decorative pillows. A cozy seating area with a light blue sofa and armchair stands nearby. Windows provide unobstructed ocean views, framed by tropical artwork and natural light.

4.92 out of 5 average rating, 249 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

A private balcony is shown, featuring colorful patio chairs and vibrant tropical plants. The space is framed by white railings and light blue shutters, creating a fresh and inviting setting for relaxation.

4.89 out of 5 average rating, 254 reviews

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.

A spacious wooden deck features two light blue lounge chairs and a white umbrella, offering a relaxing spot to enjoy ocean views. The gentle waves of the Atlantic can be seen in the background, while the shore is lined with natural sand and small rocks.

4.97 out of 5 average rating, 107 reviews

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

Condo in Key Colony Beach

The image captures a view of the Atlantic Ocean framed by lush palm trees. A pathway meanders alongside the vibrant green lawn, leading toward the beach. The clear blue sky is visible above, enhancing the calm and serene coastal atmosphere.

4.87 out of 5 average rating, 135 reviews

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.”

Superhost

A spacious living room is furnished with a soft blue sofa and matching armchair. Light wooden flooring complements the room's bright atmosphere, and a coffee table sits in the center. Large sliding glass doors lead to a patio area, allowing natural light to fill the space.

4.89 out of 5 average rating, 147 reviews

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.

A scenic view of the waterfront reveals a calm harbor lined with boat slips. The vibrant blue water reflects the sky, while a tiki hut and chaise lounge chairs surround a heated pool in the foreground, enhancing the coastal ambiance.

4.88 out of 5 average rating, 224 reviews

Florida | Waterfront 2BR/2BA w/ Pool + Dock Access

Bring friends and family to this updated 1,350 sqft waterfront corner condo in historic downtown Key West! Just 1 mile to Duval St, the Seaport, and Hemingway House. Enjoy on-site boat slips, heated pool, tiki bar, BBQ grills, parking, elevator, and secure keyless entry. Fish cleaning station and commercial ice machine available. Large park with tennis courts next door. Walk or bike everywhere—only 10 minutes from EYW airport!

4.91 out of 5 average rating, 139 reviews

A light-filled dining area features a round table surrounded by four wicker chairs, providing a cozy setting for meals. The kitchenette showcases white cabinetry and a full-sized fridge. The outdoor pool area is expansive, lined with lounge chairs and palm trees under a bright blue sky.

Condo in Marathon

Waterfront Condo w/ Pool, Tiki Bar & Marina

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.

A spacious bedroom features a dark wooden bed framed by warm lamps on either side. A gray blanket covers the bed, complemented by decorative pillows. Natural light fills the room through a large window with sheer drapes, enhancing the soft, neutral tones of the walls and flooring.

4.91 out of 5 average rating, 109 reviews

The Island Suite @ KW vacation

The Island Suite is part of a historic Key West property built around 1889. Suite #16 is located on the first floor at the rear of the 411 William Street building. The Island Suite has one of the premiere locations in Old Town, Key West with lively Duval Street just 3 blocks away and the neighborhood boasting some of the finest older homes in Key West.

A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.

5 out of 5 average rating, 41 reviews

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.

An Olympic size pool is highlighted in the image, surrounded by palm trees and lounge chairs. The building in the background offers several balconies, and a well-maintained garden area is visible, enhancing the outdoor setting next to the beach.