Key West Vacation Villas
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  • (305) 294-7358
Key West Time
October 21st
4:44pm · 88°F

Key West ~ Vacation Villas

Vacation Villas - Private 'free standing' single family homes which vary in architectural style from traditional Key West Victorian to modern. Residences range from one to five bedroom dwellings.

Choose from our inventory of Key West vacation rentals. We offer something for everyone; from charming cottages, to beachfront condos, to luxury estates, to tropical pool-garden homes.

* PLEASE NOTE: Some properties displayed may not be available for rent due to other inquires and pending reservation. Please contact our office to be sure of availability. or 305-294-7358 ext. 1

There are no properties available that fit all of your search options. Please contact our office if you would like assistance. or 305-294-7358 ext. 1

flower power house
special rates available

Nov 4- Nov 7
Nov 26- Nov 29
Nightly $800
Weekly $4900

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Standard Rates: $3950 - $8225 per week

5-6BR (Sleeping Porch) - Sleeps 12+
Attached 1BR Cottage
Overlooks Large Tropical Garden Large Shared Pool.
Boho style. Great value.
Easy walk to Higgs Beach

Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the 'real Key West'  than the shiny hotels around town.

heavenly hideout at rainbows end
special rates available

Oct 28- Nov 1
Nov 20- Nov 23
Nov 30- Dec 4
Dec 12- Dec 23
Weekly $3500
Nightly $700

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Standard Rates: $3500 - $6825 per week

4BR 4BA - Sleeps 8
Famous Mile 0 Location
1 block off Duval Street.
Custom Interior Design
Private Heated Pool
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.


ocean view luxury villa

Standard Rates: $5400 - $7900 per week

3BR 4BA – Sleeps 6-8
Ocean View - Walk to Fort Zachary Taylor Beach
Heating Swimming Pool – Sun Deck
Exclusive Truman Annex Neighborhood

If you've been searching for a Key West Ocean View Luxury Home, this could be the place for you! Holding an enviable spot in Key West’s gated community of Truman Annex, this classic home offers an open water view, easy beach access, and is a short walking distance to downtown Old Town.

key west sunset sojourn

Standard Rates: $10000 - $17000 per month

2BR + Office 3BA - Sleeps 6
Private Tropical Resort Island
Roof Top Viewing Deck
White Sandy Beaches
Oasis Swimming Pool

Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – a sojourn on a private island surrounded by sparkling turquoise waters and balmy breezes. 

dancing palms villa
special rates available

Nov 20- Dec 1
Weekly $1825

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Standard Rates: $1850 - $3525 per week

2BR 2BA - Sleeps 4
Manicured Tropical Swimming Pool Garden
Shared Heated Pool
Walk to Duval St. in 3 minutes

I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what you’ll experience as you make your entrance to this beautiful Bahamian ‘eyebrow’ style home, nestled away in private back corner of the small Old Town Key West gated community of Windward Park.

island elegance

Standard Rates: $5400 - $9500 per month

3BR 3BA - Sleeps 6
Timeless Historic Features
Split-bedroom Design
Spacious Front Porch
Tropical Landscaping
Bricked Private Driveway
Close to Key West Beaches on the South Shore

Channeling the island spirit in oft-missed mid-town, this home makes a classical curbside statement. Timeless craftsman-colonial architecture, lush mature tropical landscaping.Here you live away from the hubbub, yet close enough to beaches and Old Town. With many places to place a hammock, you may even find yourself making a new daily island ritual of swinging, reading, and sipping wine.

amelias hideaway
special rates available

Oct 30- Nov 2
Nov 18- Nov 23
Dec 10- Dec 13
Nightly $700
Weekly $3700

Jan 3- Jan 9
Six Nights $4200
Nightly $900

Jan 13- Jan 18
5 nights $3500
Nightly $900

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Standard Rates: $3600 - $7500 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."


key west wabi sabi
special rates available

Oct 28 Nov 1
Dec 16- Dec 22
Weekly $3500
Nightly $700

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Standard Rates: $3500 - $6825 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.

avant garde key west luxury home

Standard Rates: $4950 - $9500 per month

2BR 2.5BA
Sleeps 4
Premier Heart of Old Town neighborhood
Classic architecture / upscale minimalist interior renovation
Private Heated Pool

Extraordinary upscale renovation. Traditional Key West architecture is flawlessly melded with a minimalist contemporary interior. Exotic and calming, this unique home is offers all the best features of classic and modern island living.

villa deja vu key west
special rates available

Nov 18- Nov 23
Dec 9- Dec 13
Weekly $3850
Nightly $700

Dec 16- Dec 26
Weekly $5700
4 Nights $4400

Jan 12- Jan 16
Jan 23- Jan 26
4 nights $3000
nightly $900

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Standard Rates: $3500 - $7500 per week

4BR 3BA - Sleeps 8-10
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.

belle maison du port

Standard Rates: $13000 - $25000 per month

3BR 3.5BA
Victorian Home + Private Guest Cottage
Available to rent separate from the estate from May through October
Gated and Grand
Large Private Heated Pool
Premier Historic Seaport location. Steps from the boardwalk!

Extraordinary French Caribbean style Victorian home, Belle Maison du Port (Fine Harbor House), is available as a monthly vacation rental from May through November. Situated on the grounds of the Seaport Treasure Estate. Comprised of a stunningly renovated 2 – Story Victorian home, plus an adjoining one-bedroom guest cottage, and large private resort-style swimming pool.

key west spa villa
special rates available

Nov 24- Nov 28
Dec 15- Dec 19
Weekly $3900
Nightly $700

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Standard Rates: $3600 - $7500 per week

4BR 4BA - Sleeps 8
Dipping Pool w/ Waterfall
Large Hot Tub
Sun Deck
Just off Upper Duval Street

This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites.

tropical tranquility
special rates available

Nov 14- Nov 18
Dec 15- Dec 22
Weekly $3900
Nightly $1100

Jan 5- Jan 9
Jan 23- Jan 26
4 nights $3900
Nightly $1100

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Standard Rates: $3900 - $8575 per week

4BR 3.5BA - Sleeps 8
Heated Oasis Swimming Pool
Private Manicured Pool Garden
Little lane in the Heart of Old Town Key West

Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real.


private pool garden villa

Standard Rates: $3200 - $5200 per week

3BR 2.5BA - Sleeps 6
Main House
Large Private Swimming Pool
with Spacious Outdoor Cabana
Close to Higgs Beach

Experience true tropical Key West living in this lush garden oasis home with large swimming pool and garden cabana located just one block from the beach. Easy bike ride to center of Old Town.

pavilion villa
special rates available

Jan 12- Jan 17
5 nights $3500
3/4 nights $3000

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Standard Rates: $3600 - $7500 per week

4BR 3BA - Sleeps 10
Unique 2 Cottage Design
Heated Pool - Sun Deck
Deck + Balconies
1/2 Block Off Duval Street

A Private Tropical Paradise... is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St. in Old Town Key West.

tropical luxury

Standard Rates: $3500 - $6700 per week

4BR 3BA - Sleeps 7-8
Heated Free-Form Pool - Sun Deck
Heart of Old Town Key West - Preferred Heart of Old Town neighborhood

Old-world charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening heart pine from floor to ceiling, the interior rooms radiate a warm and magical feel. The grounds offer a classic front sitting porch, and generous size resort style back deck with custom free-form swimming pool.  

fantasy resort villa

Standard Rates: $3600 - $7500 per week

3BR 3BA - Sleeps 8
Just Off Upper Duval Street
Private Adjoining Cottages
with 2 Private Pools

Rare one-of-a-kind property, on Duval Street, yet hidden from the street. Two cottages jointed with a bricked courtyard and swimming pool create a secret resort residence. 

twice as nice
special rates available

Nov 18- Nov 23
Nov 30 - Dec 3
Weekly $3900
Nightly $800

Dec 23- Dec 26

Jan 2- Jan 8
6 nights $4300
Nightly $900

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Standard Rates: $3600 - $7250 per week

4BR 4BA Sleeps 8-10
Heated Pool
2 Sun Decks
2 Kitchens
On Upper Duval St. - 1 min. walk to South Beach

"Two is definitely better than One!" A rare set of early 1900's twin-cigar maker's cottages are both adorable and elegant and a perfect solution for a discerning group who want to lodge together in luxury but require maximum privacy.


the qm ~ quartermaster house key west

Standard Rates: $6000 - $10000 per month

3BR 2BA - Sleeps 6-7
Private Back Deck and garden
Shared Pool
Special Resort Amenities Gratis

Born in 1925, the Key West Quartermaster House may have found its way from the Bahamas, ‘lock stock and barrel’, during one of the most colorful points in Key West maritime history. Located in the Historic Seaport Neighborhood, today it offers all the comforts of home plus gratis resort amenities.

on hemingways rounds

Standard Rates: $4500 - $9300 per month

3BR 2BA - Sleeps 6
Private Spa Garden with Pool & Waterfall
1/2 block off Duval St.

On Hemingway's Rounds, is an inspired renovation of a classic 1930's ‘American Bungalow’ redone Key West style.  While the street side remains true to the original casual arts-and-crafts form, the interior now boasts an elegant simplicity that meets even the most discerning of modern tastes.


villa nouveau key west
special rates available

Oct 29- Nov 3
Nov 19- Nov 28
Dec 10- Dec 20
Weekly $4500
Nightly $750

Jan 21- Jan 24
Nightly $800

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Standard Rates: $3600 - $7500 per week

4BR 4BA - Sleeps 8
Heated Pool
Private Sun Deck
Steps from Duval St.

A modern interior re-design has thoughtfully transformed a prosaic 'shot-gun' cottage it into the sophisticated 'L-Shape' 4 bedroom 4 bathroom pool-side courtyard Villa Nouveau. Fabulous downtown Key West location just off-Duval St. Rent separate or with Grande Dame Key West - 'The Watson House' estate.


key west dreamin
special rates available

Nov 25- Nov 28
Dec 11- Dec 15
Nightly $450
Weekly $2500

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Standard Rates: $2300 - $4875 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

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Standard Rates: $3500 - $6700 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.

amandas dream suites

Standard Rates: $550 - $6400 per week

4-5BR (Den) 3BA - Sleeps 8-12
Bohemian Design and Decor
Large Shared Pool in Landscaped Garden
Expansive Porches
Easy Walk to Higgs Beach

Originally built in the 1938, this charming large wooden home has two full stories with deep porches which overlook the garden and pool. The floor plan was redesigned with an exterior staircase so it can also be utilized as two separate units.

governors retreat

Standard Rates: $5000 - $6600 per month

2BR 2BA - Sleeps 4
Serene setting - Large Lap Pool
Manicured Gardens
Old Town Meadows neighborhood
Easy Stroll to Historic Seaport

A luxury cottage in an idyllic retreat settng where you have the use of a manicured garden and swimming pool.  Perfectly Renovated and Immaculate Neighborhood.

mediterranean caribbean villa

Standard Rates: $5500 - $9000 per month

2BR 2.5BA - Sleeps 4
Free-form heated pool - large sun deck
Manicured Tropical Gardens
Close to Higgs Beach and stylish White St.Gallery neighborhood

Tucked behind a breathtaking tropical garden wall and located along one of Key West's most desirable residential streets, this spectacular home reflects a dynamic blend of contemporary Mediterranean and Caribbean architectural design.

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