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Below are Monthly Rentals with no specified number of bedrooms
Key West monthly vacation rentals must be rented for at least a month, but not for more than six months. Monthly rentals are designed for guests who want to experience living in Key West, settle in and enjoy the comforts of a home away from home.
Monthly rentals are furnished and decorated to provide the experience of a well-appointed local. Interior designs reflect the unique tastes of property owners. Some are luxuriously stylized, and some are furnished more simply. All are set with the essential amenities and conveniences of home, including internet, TV, linens, and kitchenware. Read our property descriptions to learn the details.
* 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. email@example.com 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. firstname.lastname@example.org or 305-294-7358 ext. 1
Standard Rates: $18000 - $25000 per month
6BR 6.5BA - Sleeps 12
Luxurious Estate ~ 2 Houses plus Guest Cottage = Private Residential Resort
Gated and Grand
Premier Historic Seaport location! Steps from the boardwalk.
A whole vacation experience for the entire family. Rent this estate and live in luxury in the most requested Historic Seaport location in Key West. Three historic dwellings are seamlessly joined to become one private luxury Key West rental estate. A combination of unique design elements impart that elusive je ne sais quoi of island architectural history. Rent the best of Key West!
Standard Rates: $3800 - $5650 per month
Overlooks large historic Meditation Garden
One Set of Stairs
Close to Higgs Beach
Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building.
Standard Rates: $4000 - $5800 per month
2 BR 1 BA
Idyllic Pool-Garden Island Cottage
Close to the Beach on a Lane
Sleeps 2 - 4
‘Heads Up’ to all of you incurable romantics who are looking for the perfect Old Town Key West garden cottage retreat close to the beach. Dream worthy and authentic, it’s a little bit like ‘Little Red Riding Hood’s cottage merges with a ‘Fantasy Island’s’ private pool garden,’ and the two are seamlessly blended.
Standard Rates: $12000 - $21500 per month
5BR + Den 5BA - Sleeps 12
Extraordinary swimming pool gardens
Famous Elizabeth St. in Historic Seaport Neighborhood
Stroll to Duval Street
Refined and Elegant. Displaying a perfected cosmopolitan flair, the designer has artfully intertwined a look-back into architectural history with a sophisticated contemporary Caribbean charm. Situated on renowned Elizabeth Street, in the historic seaport neighborhood of Old Town, this home is steeped in a colorful lore and seafaring history – so much so, it is sometimes referred to as “the pirate house.”
Standard Rates: $3200 - $4100 per month
1BR 1BA - Sleeps 1-2
Historic meditation garden.
Quiet Living Exclusive Casa Marina neighborhood.
Close to Higgs Beach
Completely hidden from the street, this historic Butteryfly Garden flat provides you with two private entrances off the large gated meditatiion garden. A private covered sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies.
Standard Rates: $5900 - $9500 per month
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.
Standard Rates: $3750 - $6000 per month
2 BR 1 BA
1 1/2 Streets Off Duval Street
Island Cottage on Charming Lane
Sleeps 2 - 6
Great for a couple or small family
Only 1 1/2 short streets off Duval St., this renovated craftsman shot-gun cottage is situated on a charming lane in Old Town Key West, in one of the most interesting Old Town residential neighborhoods of Key West. The charming curb appeal exudes Caribbean island, nestled on an eclectic gentrified tree-lined lane.
April 1- April 30
Standard Rates: $3000 - $5900 per month
3BR 2BA - Sleeps 6
View of Golf Course
Private Covered Back Deck
2 Shared Swimming Pools
Lush Tropical Landscaping
Wild Life Viewing
15 minutes from Old Town
When you awaken each day, and ponder your plans …
To tee, or not to tee: that is the question.
Whether ‘tis nobler to gaze at the peaceful scenery,
Or to take swings at golf balls on a sea of greens,
And by opposing end them? To relax: To live the Key West dream:
Standard Rates: $13000 - $25000 per month
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.
Standard Rates: $6000 - $10000 per month
3BR 2BA - Sleeps 6-7
Private Back Deck and garden
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.
Standard Rates: $4600 - $6400 per month
2BR 2BA - Sleeps 2-4
Private deck and garden
Plus Shared Manicured Swimming Pool Garden
Small pets (under 35 pounds) considered - Restrictions Apply
Everyone dreams of a charming Key West cottage tucked away in a tropical sun garden where flowers and trees flourish around an outdoor living porch all year round.
Standard Rates: $4500 - $9200 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.
Standard Rates: $18000 - $26000 per month
5BR + Den 6BA - Sleeps 10-12
Private Tropical Resort Island
Front Line Ocean Views
White Sandy Beaches
Custom Fantasy Swimming Pool w/ Waterfalls
Sit back, relax, and choose your favorite mesmerizing view from one of the magnificent private decks on this private island property, 500 yards from the ''main island' of Key West. Unhurried sunrise, serene sunset, warm turquoise waters, and white sandy beaches – from any direction, it’s divine.
Standard Rates: $5250 - $7500 per month
3BR 2BA - Sleeps 2-8
Outdoor Spa Room
Close to Higgs Beach
Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this island home is a fabulous display of tropical-modern with the perfect touch of Caribbean-Colonial architectural detail.
Standard Rates: $5000 - $6400 per month
2BR 2BA - Sleeps 4
Serene setting - Large Lap Pool
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.
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.