Vacation Rental Discounts and Special Rates

* PLEASE NOTE: The following special rates are a one time offer for the properties listed below. The rates and terms are subject to change without notice. For more information on terms and pricing please see our Rental Policies And Procedures. For faster response & more details please call 305-294-7358 ext. 1 or e-mail

There are no special deals at this time.

heavenly hideout at rainbows end
special rates available

April 29- May 10

Standard Rates: $2900 - $6700 per week

4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Sun deck on ground level

Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout Key West penthouse, you’re spot on, and you can do exactly that.


viva la links
special rates available

May 1- Sept 30

Monthly $3000

Standard Rates: $3000 - $5900 per month

3BR 2BA - Sleeps 6
View of the Golf Course Greens
Indoor - Outdoor Great-Room
Private Garden Deck
2 Shared Swimming Pools
Lush Tropical Landscaping
Wild Life Viewing
15 minutes from Old Town

On the Links with a beautiful view, creating a vibrant backdrop for your Key West indoor-outdoor lifestyle experience. Inside, joyful colors from sunshine yellow, to crimson red, to myriad shades of Caribbean Blue, dial in a playful and light-hearted tone. 

key west mile zero suite
special rates available

April 29- May 10
weekly $2000

Standard Rates: $0 - $3500 per week

2BR 2BA - Sleeps 4
2nd FL Condo Suite plus private back deck on ground level
Downtown - 1 block off 500 block of Duval Street near Margaritaville

When taking a selfie at the iconic Key West Mile Marker 0 just isn’t enough, now you can luxuriously live right next to this famous landmark ... in luxury and style!

amelias hideaway
special rates available

May 29- June 3
June 10-June 14
June 18-June 22

$600 night

Standard Rates: $3600 - $7400 per week

4BR 3.5BA - Sleeps 10
Heated Pool
Expansive Roof-Top Deck
Steps from Upper Duval Street

"In-the-know" travelers who return to Key West love to choose the more elegant area of Upper Duval St. as their favorite area to stay ... "Amelia's Hideaway."


cockadoodle cottage
special rates available

May 30- June 17
weekly $1900

Standard Rates: $1700 - $3225 per week

2BR 2BA (with Jacuzzi Bath Tub) - Sleeps 4-6
On Upper Duval St. - 1 min walk to South Beach.
Great for 2 couples or small family.

Key West cottage architecture has been time-tested in island life and culture in this infamous little wooden 'cigar maker's' cottage located on famous Duval Street, at the 'classier upper-end.'


key west wabi sabi
special rates available

June 1- June 10
July 4- July 15
weekly $3900
nightly $700

Standard Rates: $3500 - $6700 per week

4BR 3.5BA - Sleeps 8
Custom Interior Design
Heated Pool - Sun Deck
Steps from Duval St.

Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.

penthouse on duval
special rates available

June 7- June 29
weekly $3400

Standard Rates: $2900 - $6000 per week

4BR 4BA + (2 1/2 BA) - Sleeps 8
2 Kitchens
Entire 2nd + 3rd floors of the building
Porch overlooks Duval Street in the 700 Block.
Spacious deck in the back.
Adult Location

Perfectly staged on Duval Street Key West, this unique downtown Key West rental received a major renovation to become the  fabulous "Penthouse On Duval." Stroll to South Beach and Mallory Square. Plenty of room to spread out. Enviable Fantasy Fest location!  Mallory Square and the beach.

villa deja vu key west
special rates available

June 18- June 24
six nights $3600

Standard Rates: $3500 - $7400 per week

4BR 3BA - Sleeps 8
Heated Pool - Sun Deck
Lush Pool Garden
1/2 Block Off Duval Street

We invite you to discover that incredible experience of Déjà vu ... you know, when you enter someplace for the very first time, and instantly you get that sense that you’ve been there before. When I first walked into this house it happened to me. My mind sparked and I felt an instant kinship with the surroundings.

down island digs
special rates available

June 11- July 1
weekly $2300

Standard Rates: $1900 - $4175 per week

2BR 2BA - Sleeps 2-6
1/2 block off Duval Street
Unique large private manicured pool-side garden.

Everything about "Down Island Digs" adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street.


secret courtyard cottage quartet
special rates available

April 16-May 9
May 23- June 6
June 13- July 1

$1750 per week

Standard Rates: $1475 - $2800 per week

2BR 1BA - Sleeps 2-5
Private Renovated Cottage
Private Jacuzzi Tub
Steps from Duval St.

Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this hideaway, you'll never know you're right in the center of Old Town Key West.


classic key west estate
special rates available

April 29-May 3
May 9- May 13
June 4- June 8
Nightly $1100

Standard Rates: $5400 - $12100 per week

7BR 5BA - Sleeps 12-14
Heated Pool
Lush Tropical Gardens
Famous Historic Seaport neighborhood
Stroll to Duval St.

Classic Key West Estate is one of the few grand centurion wooden estate homes plus pool-side cottage, with private deck and swimming pool, licensed to rent weekly in the Historic Seaport neighborhood. It is located on famous Fleming St. with beautiful curb side appeal.

havana moon
special rates available

June 10- June 17

Standard Rates: $1900 - $4175 per week

2BR 2BA - Sleeps 4-6
Private Swimming Pool
On Upper Duval St. - 1 min. walk to South Beach.
Great for 2 couples or small family

Open the front door of this hand crafted Key West cottage and look south toward Havana Cuba and you'll catch a view of the ocean where the full moon rises with a soft salt southern breeze.


starlight siesta
special rates available

May 10- May 20
June 7- June 29
weekly $1750

Standard Rates: $1500 - $3500 per week

2BR 2.5BA - Sleeps 4
Private back deck at end of lane off Duval St. in the 700 block. Island urban. Best for Adults.

Cleverly staged in the island's city center, this downtown Key West rental is located in the 700 block of Duval Street, at the end of a narrow urban 'dead end' lane. Completely hidden from view on the 2nd and 3rd levels, spacious and creative renovation. Easy stroll to Mallory Square and South Beach.

key west dreamin
special rates available

April 29--- May 4


Standard Rates: $2300 - $4800 per week

2BR 2BA - Sleeps 4-6
Heated Pool
Private Bricked Courtyard
Lush Landscaping

This Old Town Key West premier rental home offers all the luxury amenities, including a privateback yard pool garden. Situated in a charming Upper Duval neighborhood, a stroll through the neighborhood is to rendezvous with an important part of our island's rich cigar and rum history.

lazy iguana
special rates available

June 11- June 21
weekly $3900
nIghtly $650

Standard Rates: $3500 - $6600 per week

Large Private Swimming Pool
with Spacious Outdoor Cabana
4BR 3.5BA Main house plus Studio Cottage
Sleeps 8

During the months of May through January 2,  this genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property can be your very own get-away.

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