Compare Key West Vacation Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Key West Rentals

Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Perfect Location, Private Heated Pool, Pristine Luxury Home!

Heart of Downtown Key West Cottage With Off-Street Parking

Comfortable Condo with Pool, Private Balcony, & Beach Access

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Coconut Mallory Resort And Marina By Kees Vacations
Key West Large Group Rentals

SUNKISSED ~ Come Enjoy this Charming 3 Bedroom Home When Location Is Key!

CONCH HEAVEN ~ Stylish 2B/2Ba, Sleeps 6 in Old Town w/ Heated Cocktail Pool!

LADY ADMIRAL ~ Sweet cottage & guest house with private pool off Duval!

Sept.mid wk.spec.117. lod + 10 min walk beach, close to all + full kitch& patio

ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!

DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!
How to Book Vacation Rentals in Key West
🏠 What is the best price for Key West vacation rentals?
Key West vacation rentals range in price, starting at $224 per night.
🏠 What types of vacation rentals in Key West can I rent?
Orbitz offers a wide range of Key West rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Key West condo rentals.
🏠 Is it free to cancel my Key West vacation rental with Orbitz?
Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.
🏠 How do I find the best deals to rent a Key West vacation rental with Orbitz?
There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Key West. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.
🏠 How can I cancel my vacation rental booking through Orbitz?
Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.
🏠 What are the advantages of booking a vacation rental in Key West?
Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Key West apartments and enjoy an extended stay.
🏠 Why should I book my vacation rental with Orbitz in Key West?
Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Key West package deals will get you even more savings.
More to Explore
More to Explore
- Hotels near Key West Lighthouse and Keeper's Quarters Museum
- Hotels near South Beach
- Hotels near Audubon House and Tropical Gardens
- Hotels near Duval Street
- Hotels near Oldest House Museum and Garden
- Hotels near Tennessee Williams Key West Exhibit
- Cheap Hotels in Old Town Key West
- Hotels with Pool in Old Town Key West
- Pet Friendly Hotels in Old Town Key West
- Old Town Key West Hotels
- Hotels near Harry S. Truman Little White House
- 5 Star Hotels in Truman Annex
- Hotels near Papa's Pilar Rum Distillery Hemingway Rum Company
- Hotels near St. Paul's Episcopal Church
- Hotels near Ernest Hemingway Home and Museum
- 3 Star Hotels in Key West Historic District
- 4 Star Hotels in Key West Historic District
- Kid Friendly Hotels in Key West Historic District
- Golf Resorts & in Key West Historic District
- Hotels with Balconies in Key West Historic District
- Hotels with Bar in Key West Historic District
- Hotels with Free Breakfast in Key West Historic District
- Hotels with a Gym in Key West Historic District
- Hotels with Free Parking in Key West Historic District
- Pet Friendly Hotels in Key West Historic District
- Romantic Getaways & Hotels in Key West Historic District
- Ski Resorts & in Key West Historic District
- Spa Resorts & in Key West Historic District
- Key West Historic District Hotels
- Hotels near Southernmost Point
- Hotels near Key West Cemetery
- 4 Star Hotels in Bahama Village
- 5 Star Hotels in Bahama Village
- Boutique Hotels in Bahama Village
- Golf Resorts & in Bahama Village
- Hotels with Pool in Bahama Village
- Hotels with Childcare in Bahama Village
- Hotels with Free Breakfast in Bahama Village
- Bahama Village Hotels
- Meadows Hotels
- Hotels near Waterfront Playhouse
- Beach Resorts & in Sunset Key
- Hotels on the River in Sunset Key
- Ski Resorts & in Sunset Key
- Sunset Key Hotels
- Hotels near Key West Shipwreck Museum
- Hotels near Custom House Museum
- Hotels near Jackson Square
- White Street Gallery District Hotels
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Simonton Beach
- Hotels near Donkey Milk House
- Hotels near Red Barn Theater
- Hotels near Mallory Dock
- Hotels near MLK Community Pool & Community Center
- Hotels near Curry Mansion Museum
- Hotels near Mallory Square
- Hotels near Florida Keys Eco - Discovery Center
- Hotels near Key West Butterfly and Nature Conservatory
- Cheap Hotels in Downtown Key West
- Hotels with Pool in Downtown Key West
- Pet Friendly Hotels in Downtown Key West
- Hotels near Florida Keys National Marine Sanctuary
- 5 Star Hotels in Historic Seaport
- Beach Resorts & in Historic Seaport
- Historic Seaport Hotels
- Duval Street
- Sails To Rails Museum at Flagler Station
- San Carlos Institute - Casa Cuba
- Ernest Hemingway Home and Museum
- Southernmost Point
- The Kite House
- Fort Zachary Taylor Historic State Park
- Donkey Milk House
- Mlk Community Pool & Community Center
- Florida Keys Eco - Discovery Center
- Key West Butterfly and Nature Conservatory
- Car rentals near Uptown - Upper Duval
- Car rentals near Key West Historic District
- Avis Rental Cars in Sunset Key
- Budget Rental Cars in Sunset Key
- Car rentals near Sunset Key
- Hertz Rental Cars in Sunset Key
- National Car Rental Rental Cars in Sunset Key
- Sixt Rental Cars in Sunset Key
- Thrifty Car Rental Rental Cars in Sunset Key
- Everglades City Vacation Rentals
- Key Haven Vacation Rentals
- Lower Florida Keys Vacation Rentals
- Chokoloskee Island Vacation Rentals
- Conch Key Vacation Rentals
- Bahia Honda Key Vacation Rentals
- Lower Keys Vacation Rentals
- Big Pine Key Vacation Rentals
- Boca Chica Key Vacation Rentals
- Marathon Vacation Rentals
- Islamorada Vacation Rentals
- Cudjoe Key Vacation Rentals
- Sugarloaf Key Vacation Rentals
- Hotels in Key West Historic District
- Hotels near Duval Street
- Visit Harry S. Truman Little White House
- Hotels in Old Town Key West
- Visit Duval Street
- Hotels near Ernest Hemingway Home and Museum
- Key West vacation rentals
- Hotels in Truman Annex
- Visit Ernest Hemingway Home and Museum
- Hotels near Mallory Square