Owner Direct Short Term Stays in Key West
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Explore the Best Key West Short Term Stays
Looking for the perfect Short Term Stays in Key West? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Key West character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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What makes our vacation homes stand out?

Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.

Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.

Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Key West vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
How to Reserve Your Key West Short Term Stays
Booking Made Simple
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Key West Short Term Stays FAQs
There are a lot of options in Key West. If you plan on staying in the Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the top Short Term Stays in Key West:
- Spring into Dubuque: Stroll, Shop, Sip & Stay in our Charming Cozy Bungalow!
- 3bed 2bath nestled in cozy Grandview neighborhood (pet friendly!)
- Custom Floating Cabin on Mississippi River backwater with a HOT TUB!
- Retro floating cabin on river backwaters. HOT TUB!
- Annabel Lee Barn ~ A Getaway of Warmth & Charm!
- Floating Studio Cabin. HOT TUB!
- 1970s Modern Floating River Cabin-HOT TUB!
- The Aster Cabin. 10 Minutes from Downtown Dubuque. Lorelei Cabin Collection
- The Edelweiss Cabin. 10 minutes from Downtown Dubuque. Lorelei Cabin Collection.
- Midcentury Modern Getaway * Quiet Neighborhood
At Ownerdirect short-term furnished accommodation in or near Key West ranges from $60 to $1,184 per night.
We have 2 places to stay near Key West. Check out the complete list of holiday rentals in Key West to find what works for your next trip.
Yes, there are 2 self-catering short-term rental homes in Key West that have hot tubs & other amenities The most popular self-catering top-rated rental homes are:
- Hidden Gem! Uniquely, fully-furnished, newly remodeled, 1860’s carriage house
- Jacuzzi tub - fireplace - Self check-in- off street parking!
- 3bed 2bath nestled in cozy Grandview neighborhood
- Spring into Dubuque: Stroll, Shop, Sip & Stay in our Charming Cozy Bungalow!
- Days Inn by Wyndham Dubuque
- Family friendly spacious with jacuzzi & fireplace!
There are more than 2 luxury temporary places to stay near Key West, with other amenities available according to 2026 data from Ownerdirect.



