Compare Fleming Key Villas

Start date: Check-in selected.
To Date
End date: Check-out

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 Fleming Key

Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

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
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

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
Secret Villa II @ Old Town: with Private Pool, close to Duval!

Secret Villa II @ Old Town: with Private Pool, close to Duval!

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
Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!

$685 nightly
The price is $760 total per night
$760 total
Nov 12 - Nov 13
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!

Two Bedroom Two Bath Balcony Villa Steps from Duval!

$614 nightly
The price is $683 total per night
$683 total
Nov 3 - Nov 4
Total with taxes and fees
This villa features a hot tub and laundry facilities.
Pool
Hot Tub
Secret Villa I @ Old Town with Private Pool, close to Duval!

Secret Villa I @ Old Town with Private Pool, close to Duval!

This villa offers a terrace, laundry facilities, and local meal delivery service. Helpful staff is there to provide concierge services, as well as offer insight about the area. Additional amenities include a garden and barbecue grills.
Pool
Kitchen
Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access

Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access

At this villa, guests have access to features like laundry facilities. This smoke-free villa also has a garden.
Pool
Kitchen
Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool

4 out of 5
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
Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!

Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!

At this villa, guests have access to features like laundry facilities.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Fleming Key
View all properties
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 Fleming Key

    Oceans Edge Key West Resort, Hotel & Marina

    Oceans Edge Key West Resort, Hotel & Marina

    5950 Peninsular Avenue, Key West, FL
    $189 nightly
    The price is $212 total per night from Oct 28 to Oct 29
    $212 total
    Oct 28 - Oct 29
    Total with taxes and fees
    8.8/10 Excellent! (1,742 reviews)
    Margaritaville Beach House Key West

    Margaritaville Beach House Key West

    2001 South Roosevelt Boulevard, Key West, FL
    $235 nightly
    The price is $264 total per night from Nov 18 to Nov 19
    $264 total
    Nov 18 - Nov 19
    Total with taxes and fees
    8.6/10 Excellent! (1,784 reviews)
    Southernmost Beach Resort and Guesthouses

    Southernmost Beach Resort and Guesthouses

    1319 Duval Street, Key West, FL
    $211 nightly
    The price is $238 total per night from Oct 30 to Oct 31
    $238 total
    Oct 30 - Oct 31
    Total with taxes and fees
    8.6/10 Excellent! (2,804 reviews)

Luxury Villas

Book luxury villas in Fleming Key
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Fleming Key. 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 Fleming Key, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Fleming Key
You won’t have a problem finding your own space in Fleming Key. 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 Fleming Key on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Fleming Key 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!

Fleming Key Villas essential information

Accommodation
16 Villas
Lowest Price
$212
Highest Price
$760
Popular accommodation
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking, Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere, Secret Villa II @ Old Town: with Private Pool, close to Duval!, Two Bedroom Two Bath Poolside Villa Steps from Duval!, Two Bedroom Two Bath Balcony Villa Steps from Duval!, Secret Villa I @ Old Town with Private Pool, close to Duval!, Admirals Gold Key West - Truman Annex Villa - Close to Beach and Duval w Parking and Pool Access, Coral Garden by Avantstay Great Location w/ Balcony & Shared Pool, Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!

More to Explore