
Condo vacation rentals in Key West
Find and book unique condos on Airbnb
Quick stats about condo rentals in Key West

Total vacation rentals
Explore 420 vacation rentals in Key West

Nightly prices starting at
Key West vacation rentals start at $127 CAD per night before taxes and fees

Verified guest reviews
Over 16,980 verified reviews to help you choose

Family-friendly vacation rentals
330 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Vacation rentals with a pool
380 properties feature pools

Rentals with dedicated workspaces
190 properties have a dedicated workspace

Wifi availability
410 of Key West vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Key West rentals

4.8 Average rating
Key West stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated condo rentals in Key West
Guests agree: these condos are highly rated for location, cleanliness, and more.

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

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.

Waterfront Condo Dock Pool Near Duval St
Relax above it all in this spacious top-floor waterfront condo in downtown Key West, offering added privacy and sweeping marina views. Perfect for families and groups, enjoy a full kitchen, open living space, and private balcony. Dockage available with a fish cleaning station and ice maker, ideal for boating and fishing. Located about 1 mile from Duval Street, restaurants, and nightlife, and 10 minutes from EYW airport, with a heated pool, tiki area, BBQ grills, parking, and secure entry.

Orchid Suite @ the Old Town Villas, steps from
The Orchid Suite is a bi-level suite decorated in a rich contemporary Danish style. The bedroom is located upstairs with a bookcase divider separating two different sleeping areas, each with a queen bed. The upstairs bathroom features a tiled shower with a glass door, hairdryer, and all necessary linens. Large beach towels are also provided. Downstairs is a living room. With A/C, ceiling fans, a TV, DVD player, stereo with CD player, and free wi-fi you can keep cool and connected to the

Exquisite Oceanfront Paradise - Key Colony Beach
Stunning direct ocean views. Everything is brand new in this gorgeous condo with comfy king bed and fully equipped kitchen with full-size appliances and everything you need to cook and serve meals. Fast, free, reliable WiFi, and SmartTV to enjoy your favorite movies and shows. Heated pool and private sandy beach just steps away. Sunset Park next door is perfect for catching beautiful nightly sunsets. Centrally located to awesome Keys adventures just a few miles drive from the condo.

Waterfront Condo, daily housekeeping & breakfast!
Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and 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!

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.

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.

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.

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.

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!

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.
Popular amenities for Key West condo rentals
Weekly condo rentals

Seas the Breeze – Poolside Condo Near the Beach

Condo de Paradise/Salt Water Pool/Boat Dock

Palm Garden retreat with Hot Tub & Prime Key West

Bright Condo in Paradise

Private Beach in Marathons Key Colony Beach

Sky Loft - Steps from Duval Street & Shared Pool

EYW Getaway

2 BR Condo Banyan Tree, Key West,FL
Pet-friendly condo rentals

Steps to Duval! Old Town. 3 blks to South Beach

180 Degrees of Ocean Views, Lagoon and Florida Bay

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Andy’s Attic | Budget-Friendly!

Seashells Getaway - Pool, Boat Slip/Parking/Ramp

Walkable 1BR | Deck | Pool | Dog Friendly

La Maisonnette~ Gated Condominium 1 Block to Duval

Waterfront Condo + Dock Pool Downtown Near Duval
Condo rentals with a pool

Island Time - Old Town Key West

Resort Escape | Pool+Hot Tub | Sleeps 6

Pool View Suite | Beachside Resort

Hyatt Beach House-Quiet Key West Spot!

2-story condo w/ panoramic bay views and balconies

Steps to Duval Street, beach, Mallory Square, more

Paradise found! Sea-Esta Condo beach and pool.

Charming Key West By the Sea
When is the best time to visit Key West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $587 CAD | $720 CAD | $686 CAD | $478 CAD | $444 CAD | $404 CAD | $417 CAD | $380 CAD | $330 CAD | $401 CAD | $485 CAD | $563 CAD |
| Avg. temp | 21 °C | 22 °C | 24 °C | 25 °C | 27 °C | 29 °C | 30 °C | 30 °C | 29 °C | 27 °C | 25 °C | 23 °C |
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- Sombrero Beach
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