Key West Vacation Rentals and Vacation Homes

Vacation Homes Of Key W...
888-404-2802

From charming little cottages to elegant luxurious estates, experience the original island charm of Key West through our variety of top qu...

Browse 71 Vacation Rentals

Rentalsfloridakeys.com
305-743-5181, 888-743-5635

Florida Keys Vacation Rentals manages hundreds of vacation rental properties ranging from luxurious to budget-conscious throughout The Flo...

Browse 321 Vacation Rentals

RentKeyWest.com
305-294-0990

Key West, FL Rent a private home, cottage, villa, or condo as an alternative to your typical Key West hotel stay.

Browse 85 Vacation Rentals

trumanannex.com
305-292-1881

We are the exclusive on-site rental agency for the Truman Annex and Key West Golf Club. Our staff of professional, licensed Realtors® is ...

Browse 164 Vacation Rentals

AtHomeKeyWest.com
888-459-9378

Located throughout Key West many homes, cottages and compounds are open for vacation rentals. These homes offer a private haven in the tro...

Browse 88 Vacation Rentals

347 Rentals in Key West

Displaying 1-25 of 347

Property 19796

Family Reunion KEYS

12 Bedroom Family Reunion Vacation Rental - Key West
House in Key West (Near Old Town)
12 Bedroom(s), Sleeps 22-28
8 Bathroom(s)
Weekly Rates from $7,500

Property 19247

South Point Selection

South Point Selection 7 Bedroom Home - Key West
House in Key West
7 Bedroom(s), Sleeps 14-16
6.5 Bathroom(s)
Weekly Rates from $6,700

Property 19250

Key West Coral Country 30

Key West Luxury Home
Townhouse in Key West (Near Old Town)
7 Bedroom(s), Sleeps 16
9 Bathroom(s)

Property 19252

Grande Dame Key West 525

Grande Dame Key West Vacation Rental - Exclusive Heart of Old Town Location - Amazing Luxury Mansion Estate - Key West
House in Key West
7 Bedroom(s), Sleeps 16
7 Bathroom(s)
Weekly Rates from $6,800

Property 19251

Island Rendezvous 5730

Island Rendezvous Vacation Rental - Key West
Villa in Key West (Near Old Town)
6 Bedroom(s), Sleeps 14
5 Bathroom(s)
Weekly Rates from $5,850

Property 19793

Classic Key West Estate

Classic Key West Estate Vacation Rental
House in Key West (Near Old Town)
6 Bedroom(s), Sleeps 12-14
4 Bathroom(s)
Weekly Rates from $5,000

Property 31946

The Watson House

Award Winning Victorian Home in the Heart of Old Town Key West.
House in Key West (Near Old Town)
6 Bedroom(s), Sleeps 12
4 Bathroom(s)
Weekly Rates from $5,400

Property 58629

Duval Compound

Duval Compound - Great property for your large group or family
House in Key West
6 Bedroom(s), Sleeps 14
5.5 Bathroom(s)
Weekly Rates from $7,500

Property 19246

Victorian Mansion 4379

Victorian Mansion Vacation Rental - Key West
House in Key West (Near Old Town)
5 Bedroom(s), Sleeps 10
3 Bathroom(s)
Weekly Rates from $4,450

Property 19792

Amanda's Dream Suites

Amanda's Dream Suites Vacation Rental - Key West
House in Key West (Near Old Town)
5 Bedroom(s), Sleeps 8-10
3 Bathroom(s)
Weekly Rates from $3,100

Property 28715

The Victoria House

The Victoria House - Historical Property - Walk to Duval Street
House in Key West
5 Bedroom(s), Sleeps 12
5.5 Bathroom(s)
Weekly Rates from $5,500

Property 57895

Real World Key West

Luxurious Home of the Real World Key West
House in Key West
5 Bedroom(s), Sleeps 20
4.5 Bathroom(s)
Weekly Rates from $7,000

Property 91007

Casa Del Mar

Casa Del Mar
House in Key West
5 Bedroom(s), Sleeps 12
5 Bathroom(s)
Weekly Rates from $9,000

Property 10858

Villa Tropicale

"Villa Tropicale" This Magnificent Vacation Rental Home is Best Described as Tropical Seclusion
House in Key West
4 Bedroom(s), Sleeps 9
5 Bathroom(s)
Weekly Rates from $4,830

Property 10863

Southard Street

Key West Vacation Rentals
House in Key West (Near Old Town)
4 Bedroom(s), Sleeps 14
4 Bathroom(s)
Weekly Rates from $4,760

Property 19243

Amelia's Hideaway 3714

Amelia's Hideaway Vacation Rental - Key West
Villa in Key West (Near Old Town)
4 Bedroom(s), Sleeps 2-10
3.5 Bathroom(s)
Weekly Rates from $3,800

Property 19790

Pavilion Villa

Pavilion Villa Vacation Rental - A Private Tropical Paradise - Key West
Villa in Key West
4 Bedroom(s), Sleeps 10
3 Bathroom(s)
Weekly Rates from $3,800

Property 23187

Amelia's Great Escape

"Amelia's Great Escape "Tucked Away Getaway In The Heart Of Old Town
House in Key West
4 Bedroom(s), Sleeps 8-11
3 Bathroom(s)
Weekly Rates from $3,150

Property 31921

Tropical Tranquility

Luxury Villa in the Heart of Key West with Guest Cottage
Villa in Key West
4 Bedroom(s), Sleeps 8
3.5 Bathroom(s)
Weekly Rates from $4,500

Property 31947

Twice as Nice

Twin Cottages On Duval Street,Pool,Sun Deck,Nice Sitting Front Porch.
Cottage in Key West
4 Bedroom(s), Sleeps 4-8
4 Bathroom(s)
Weekly Rates from $3,550

Property 31951

Luxurious Manor

Luxurious Key West Vacation Home
House in Key West
4 Bedroom(s)

Property 31968

Island Interlude

Cottage in the heart of Old Town Key West,Pool,Historic Neighborhood.
Cottage in Key West
4 Bedroom(s), Sleeps 8-10
4 Bathroom(s)

Property 44507

Louisa House

Wonderful Key West Location - Louisa House
House in Key West
4 Bedroom(s), Sleeps 8
3.5 Bathroom(s)
Weekly Rates from $3,150

Property 44512

Bloom'n Paradise

Apartment in Key West
4 Bedroom(s), Sleeps 8
4 Bathroom(s)
Weekly Rates from $5,000

Property 58590

Casa Laguna

Key West Vacation Rentals House
House in Key West
4 Bedroom(s)
2.5 Bathroom(s)