Charming Studio with porch - great location!
Charming Studio with porch - great location!
Charming Studio with porch - great location!
Charming Studio with porch - great location!
Charming Studio with porch - great location!

Charming Studio with porch - great location!

1 bedroom·1 bath
Key West • Florida

$4,941.00 USD total for 28 nights

Nov 25 – Dec 23, 2026

Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location
Old Town 1B Apartment / Balcony / Great Location

Old Town 1B Apartment / Balcony / Great Location

1 bedroom·1 bath
Key West • Florida

$3,460.00 USD total for 28 nights

Mar 1 – 29, 2027

Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District
Garden Apartment Sanctuary in Historic District

Garden Apartment Sanctuary in Historic District

0 bedrooms·1 bath
Key West • Florida
5(7 reviews)

$7,484.63 USD total for 28 nights

Mar 1 – 29, 2027

Old Town Gated Studio, Great Location, Great Value
Queen murphy bed below, queen loft bed above.
Loft queen bed
Queen Murphy Bed
Old Town Gated Studio, Great Location, Great Value

Old Town Gated Studio, Great Location, Great Value

0 bedrooms·1 bath
Key West • Florida
5(6 reviews)

$3,876.75 USD total for 28 nights

Dec 2 – 30, 2026

Sunny tropical patio with bistro set, grill & French doors
Sunny studio with lounge nook, queen bed, AC & dining table
Cozy loft retreat with skylight, TV, and built-in storage.
Bright modern kitchen with stainless suite, gas range, and dining nook
Sleek bath with frameless walk-in shower, bench, and subway tile

Beach House Modern Old Town Studio Near Duval

1 bedroom·1 bath
Key West • Florida
5(1 review)

$4,156.88 USD total for 28 nights

Nov 30 – Dec 28, 2026

Welcome to Stay Anchored at Sombrero. View from across the canal.
Open floor plan - kitchen, dining room and living room.
Fully-stocked kitchen.
Living room with sectional, two accent chairs and entertainment console.
Main Entrance Side & Stairs

Stay Anchored at Sombrero

4 bedrooms·3 baths
Marathon • Florida
5(19 reviews)

$4,432.46 USD total for 7 nights

Feb 27 – Mar 6, 2027

Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval
Coral Palms 1BR/King/Queen, Pool, block to Duval

Coral Palms 1BR/King/Queen, Pool, block to Duval

1 bedroom·1 bath
Key West • Florida
5(64 reviews)

$22,533.75 USD total for 28 nights

Mar 1 – 29, 2027

Living Area
Breakfast Bar with seating for 4
Duval Corner - Pet friendly with Balcony
Duval Corner - Pet friendly with Balcony
Duval Corner - Pet friendly with Balcony

Duval Corner - Pet friendly with Balcony

1 bedroom·1 bath
Key West • Florida

$969.00 USD total for 3 nights

Nov 18 – 21, 2026

Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool
Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool
Relax in paradise with our brand-new hot tub, added March 2025, just 0.5 blocks from Duval Street! 🏝️💦 Perfect for unwinding after a day of Key West adventures.
Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool
Bright and open kitchen and dining area, perfect for cooking meals and gathering around the table. Enjoy all the comforts of home with plenty of space to dine and relax.

Island Paradise - Half Block from Duval, 2.5BR, 2BA with Pool

2 bedrooms·2 baths
Key West • Florida
5(1 review)

$9,564.50 USD total for 28 nights

Apr 1 – 29, 2027

Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.
Welcome to Casa Rosa, your tropical sanctuary nestled in the vibrant heart of Key West, Florida.
Unwind in your private tropical oasis, where lush greenery surrounds a serene pool. Sip your morning coffee or enjoy an al fresco meal on the spacious deck
Take a dip in your private pool, tucked away amidst lush, tropical foliage. Perfect for a refreshing morning swim or a relaxing evening-this retreat invites you to embrace the laid-back charm of the Keys.

Casa Rosa: Historic Key West Home with Pool, 1 Block from Duval

4 bedrooms·4 baths
Key West • Florida
5(9 reviews)

$9,995.73 USD total for 7 nights

Jan 2 – 9, 2027

Bright living room with comfortable seating and historic Key West character
Refreshing swimming pool surrounded by tropical landscaping
Compact kitchen with everything needed for a comfortable stay
Private balcony overlooking the colorful streets of Duval Street
Inviting living space with exposed wood ceiling and Smart TV

Shipwreck Suite

1 bedroom·1 bath
Key West • Florida

$16,309.00 USD total for 28 nights

Feb 6 – Mar 6, 2027

Lush tropical gardens surround the private swimming pool, creating a peaceful oasis in the heart of Key West’s historic Old Town.
Elegant first floor living room featuring comfortable seating, a fireplace, large windows, and classic Key West architectural details.
The historic William Skelton Home, a beautifully preserved Key West residence surrounded by tropical landscaping in the heart of Old Town.
Relax on the spacious second floor porch with comfortable seating, surrounded by lush tropical landscaping and the beautiful architecture of historic Key West.
Third floor primary suite with vaulted wood ceilings, comfortable seating, a king bed, and beautiful architectural details.

William Skelton Home

6 bedrooms·4 baths
Key West • Florida

$4,006.75 USD total for 3 nights

Dec 6 – 9, 2026

Relax on the spacious second floor front porch with comfortable seating, surrounded by lush tropical greenery and beautiful views of historic Old Town Key West.
Private heated swimming pool surrounded by lush tropical gardens, creating a peaceful and secluded oasis in the heart of historic Old Town Key West.
Elegant living room with comfortable seating, a fireplace, large windows, and original architectural details that showcase the character of this historic Key West home.
Third floor primary suite featuring a king bed, vaulted wood ceilings, a cozy sitting area, and beautiful architectural details.
Lush tropical backyard surrounding the private swimming pool, offering a peaceful place to relax and enjoy the laid back atmosphere of Key West.

William Skelton Home - Upstairs

3 bedrooms·2 baths
Key West • Florida

$3,087.90 USD total for 3 nights

Dec 6 – 9, 2026

Private patio with outdoor dining and comfortable lounge seating
Bright living room with comfortable seating and exposed wood ceiling
Shared swimming pool surrounded by tropical landscaping
Well equipped kitchen with modern appliances and granite counters
Inviting private porch with comfortable outdoor seating

Old Town Key West Cottage

2 bedrooms·1½ baths
Key West • Florida

$8,080.01 USD total for 28 nights

Apr 15 – May 13, 2027

Duval & Catherine St
Duval & Catherine St
Duval & Catherine St
Duval & Catherine St
Duval & Catherine St

Duval & Catherine St

2 bedrooms·1 bath
Key West • Florida

$10,052.00 USD total for 28 nights

Apr 2 – 30, 2027

Well appointed kitchen with generous counter space
Charming decorative details throughout the home
Inviting primary suite with king bed and private outdoor access
Comfortable living room with French doors and natural light
Quiet porch tucked into a peaceful tropical setting

Casa Mamisa

2 bedrooms·2 baths
Key West • Florida

$16,250.25 USD total for 28 nights

Mar 1 – 29, 2027

Breathtaking open views of the Gulf of America, right from your private dock
Your private pool and stunning gulf views await at Caribbean Sunsets
Enjoy breathtaking sunsets right from the comfort of the house
Dive into relaxation with your private pool and hot tub, surrounded by lush tropical greenery
Dine with a stunning Gulf-front view right on your private patio

Caribbean Sunsets: Open Gulf Views with Private Dock and Pool

3 bedrooms·3 baths
Marathon • Florida
5(4 reviews)

$3,442.75 USD total for 7 nights

Nov 28 – Dec 5, 2026

Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats
Marathon Gulfside Lake view home, bring your boats

Marathon Gulfside Lake view home, bring your boats

4 bedrooms·3½ baths
Marathon • Florida
$1,000/ night(excl. fees & taxes)
Open Gulf Views with Private Pool and Dock
Oceanfront Paradise: Your Private Oasis
Oceanfront Paradise: Your Private Oasis
Golden hour over the Gulf of America—experience breathtaking sunsets from your private paradise
Spacious patio featuring a pool, hot tub, and comfortable lounge chairs

Tropical Sunsets: Open Gulf Views with Private Dock and Pool

4 bedrooms·3 baths
Marathon • Florida
5(4 reviews)

$3,865.75 USD total for 7 nights

Dec 12 – 19, 2026

Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets
Marathon Sleeps 8 | Hot Tub • Game Room • Pets

Marathon Sleeps 8 | Hot Tub • Game Room • Pets

3 bedrooms·2 baths
Miami • Florida
4.9(29 reviews)

$1,985.53 USD total for 7 nights

Nov 27 – Dec 4, 2026

Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ
Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ

Tropical Oasis! Private Pool, Dock, Tiki Hut & BBQ

3 bedrooms·2 baths
Marathon • Florida
4.94(16 reviews)

$2,924.00 USD total for 7 nights

Dec 5 – 12, 2026

Enjoy your own private movie theater, promising cinematic magic in a serene ambiance under the stars. You can also dip into your own private hot tub and enjoy a movie, the stars and the calm & private twilight hues
Craving a morning or afternoon coffee? We have you covered with your very own coffee making Keurig machine and if you want an espresso, we have a nespresso machine too. The kitchen comes with espresso/coffee pods to flavor your coffee just right
Family movie nights just got an upgrade—unwind under the stars with a cozy family film, all set beneath the shade of our beautiful tropical tree. **Some photos include lightly enhanced or staged scenes to help show how the space can be enjoyed.
Family movie nights just got an upgrade—unwind under the stars with a cozy family film, all set beneath the shade of our beautiful tropical tree. **Some photos include lightly enhanced or staged scenes to help show how the space can be enjoyed.
Enjoy your very own pool for summer cool-offs. You can also relax on a lounge chair and soak in the evening serenity

Keys Getaway - Pool, Hot Tub & Movie Theater

3 bedrooms·3 baths
Marathon • Florida

$4,027.50 USD total for 7 nights

Nov 21 – 28, 2026

View of Cove from Backyard
Another Great Sunset
Home from the Water (Yellow)
Living Room
Kitchen

Waterfront Keys Home - Spectacular View, 37' Dock

2 bedrooms·2 baths
Marathon • Florida
4.33(3 reviews)

$1,408.00 USD total for 7 nights

Nov 28 – Dec 5, 2026

A View from the Backyard
Hose from the Water (yellow house)
Unobstructed View, 38' Deep Water Dock
Sunset from Yard
Kitchen

Waterfront Home - Incredible View, 37' Dock, Kayak

2 bedrooms·2 baths
Marathon • Florida
4.77(13 reviews)

$1,634.63 USD total for 7 nights

Nov 27 – Dec 4, 2026