Compare Key West Villas
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
Featured Villas in Key West
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Key West FL
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Key West FL
$685 nightly
The price is $760 total per night
$760 total
Dec 20 - Dec 21
Total with taxes and fees
Guests staying at this villa enjoy a hot tub and laundry facilities.
Pool
Hot Tub
Two Bedroom Two Bath Balcony Villa Steps from Duval!
Key West FL
$904 nightly
The price is $1,004 total per night
$1,004 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
This villa features a hot tub and laundry facilities.
Pool
Hot Tub
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
key west FL
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. This smoke-free villa also has barbecue grills.
Pool
Hot Tub
Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access
Key West FL
At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
Secret Villa II @ Old Town: with Private Pool, close to Duval!
Key West FL
This villa offers a water park, an outdoor pool, and laundry facilities. Staff members can answer questions about accommodations, and also provide concierge services. Other amenities at this family-friendly villa include local meal delivery service, barbecue grills, and a garden.
Pool
Kitchen
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool
12 Coral Way Key West FL
Guests staying at this villa enjoy an outdoor pool, free WiFi in public areas, and a garden. If you decide to drive, there's free parking. Friendly staff can provide concierge services, and also offer advice about sightseeing.
Pool
Kitchen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Hotel Options in Key West
Beachside Resort & Residences
3841 N Roosevelt Blvd Key West FL
$235 nightly
The price is $265 total per night from Dec 18 to Dec 19
$265 total
Dec 18 - Dec 19
Total with taxes and fees
8.6/10 Excellent! (1,780 reviews)
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
$171 nightly
The price is $192 total per night from Dec 18 to Dec 19
$192 total
Dec 18 - Dec 19
Total with taxes and fees
8/10 Very Good! (1,763 reviews)
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
$253 nightly
The price is $285 total per night from Dec 18 to Dec 19
$285 total
Dec 18 - Dec 19
Total with taxes and fees
8.6/10 Excellent! (2,924 reviews)
Luxury Villas
Book luxury villas in Key West
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Key West. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Key West, so book one now. You’ll feel like a million bucks before you even check in.
Spacious luxury villas in Key West
You won’t have a problem finding your own space in Key West. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Key West on your own and use a one-bedroom villa as your home base.
A top-end villa experience in Key West rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!
Key West Villas essential information
Accommodation | 32 Villas |
|---|---|
Lowest Price | $192 |
Highest Price | $1,004 |
Popular accommodation | Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere, Two Bedroom Two Bath Poolside Villa Steps from Duval!, Two Bedroom Two Bath Balcony Villa Steps from Duval!, Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking, Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access, Secret Villa II @ Old Town: with Private Pool, close to Duval!, Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool, AZURE KEY WEST - Stunning New Home with Heated Pool - 4 Bedrooms Available, Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool |
More to Explore
- Hotels near Key West Lighthouse and Keeper's Quarters Museum
- Hotels near Audubon House and Tropical Gardens
- Hotels near Tennessee Williams Key West Exhibit
- Hotels near Mallory Dock
- Inns in Monroe County
- Town Houses in Monroe County
- Hotels near Florida Keys Eco - Discovery Center
- Hotels near MLK Community Pool & Community Center
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Southernmost Point
- Hotels near Waterfront Playhouse
- 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
- Hotels near Curry Mansion Museum
- 5 Star Hotels in Historic Seaport
- Beach Resorts & in Historic Seaport
- Historic Seaport Hotels
- 5 Star Hotels in Truman Annex
- B&B in Stock Island
- Condo Rentals in Stock Island
- Houseboats in Stock Island
- Vacation Homes in Stock Island
- Resorts in Stock Island
- Hotels near Key West Butterfly and Nature Conservatory
- Hotels near Papa's Pilar Rum Distillery Hemingway Rum Company
- Apartments in Cow Key
- B&B in Cow Key
- Cabin Rentals in Cow Key
- Condo Rentals in Cow Key
- Cottages in Cow Key
- Hostels in Cow Key
- Houseboats in Cow Key
- Vacation Homes in Cow Key
- Rv Parks in Cow Key
- Villas in Cow Key
- Hotels near Jackson Square
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Red Barn Theater
- 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 Key West Shipwreck Museum
- Hotels near Custom House Museum
- Hotels near Donkey Milk House
- Apartments in Fleming Key
- B&B in Fleming Key
- Cottages in Fleming Key
- Guest Houses in Fleming Key
- Hostels in Fleming Key
- Houseboats in Fleming Key
- Resorts in Fleming Key
- Apartments in Dredgers Key
- Cabin Rentals in Dredgers Key
- Cottages in Dredgers Key
- Hostels in Dredgers Key
- Houseboats in Dredgers Key
- Villas in Dredgers Key
- Hotels near Mallory Square
- Hotels near St. Paul's Episcopal Church
- 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
- Guest Houses in Flamingo
- Hotels near Harry S. Truman Little White House
- Hotels near Duval Street
- Hotels near Key West Cemetery
- Hotels near Oldest House Museum and Garden
- 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 in Truman Annex
- Visit Duval Street
- Visit Harry S. Truman Little White House
- Hotels in Old Town Key West
- Hotels in Key West Historic District
- Villas in Key West
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Mallory Square
- Hotels near Duval Street
- Visit Ernest Hemingway Home and Museum