Fire table and sitting area near pool watching boats pass through canal.
Resort style inground pool and hot tub.
Inground hot tub, floating double jet ski dock.
Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean
Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean

Pool-2 HotTubs-Boat Lift-Easy Access to Gulf&Ocean

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

$14,536.40 USD total for 28 nights

Sep 7 – Oct 5, 2026

Casa West Indies
Casa West Indies
Casa West Indies
Casa West Indies
Casa West Indies

Casa West Indies

2 bedrooms·2 baths
Summerland Key • Florida
$400/ night(excl. fees & taxes)
Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool
Keys Waterfront- Spectacular Gulf View, Dock, Pool

Keys Waterfront- Spectacular Gulf View, Dock, Pool

3 bedrooms·1 bath
Marathon • Florida
4.5(10 reviews)

$2,413.13 USD $2,300.91 USD total for 7 nights

Sep 7 – 14, 2026

Huge seasonally heated pool
Tropical tiki bar with BBQ grill and bright seating—al fresco fun
Bright open-plan living with cozy sleeper sectional, dining, and kitchen
Two queen beds on third floor
Sunny bedroom with King bed and playful cat quilt, cozy lighting and ample storage.

Cathouse Old Town Oasis Huge Heated Pool & Parking

4 bedrooms·2½ baths
Key West • Florida
5(72 reviews)

$2,439.00 USD total for 3 nights

Sep 7 – 10, 2026

Kittyhouse on Catherine, Tropical Pool, Parking
Breakfast bar
full kitchen
2nd floor bathroom
first floor half bathroom

Kittyhouse on Catherine, Tropical Pool, Parking

2 bedrooms·1½ baths
Key West • Florida
Private tropical plunge pool with waterfall and sunny brick patio
Elegant Old Town gem with double porches and a white picket fence
Bright, open living room with comfy seating and coastal flair
Spacious chef’s kitchen with granite, stainless appliances, and patio access
Sunny dining room for 10 with hardwoods, French doors, and ceiling fan

Cockhouse 3BR/3BA Privt Pool/Parking/Pets Old Town

3 bedrooms·3 baths
Key West • Florida
5(1 review)

$6,925.50 USD total for 28 nights

Sep 7 – Oct 5, 2026

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)
$89 – $359/ night(excl. fees & taxes)
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)

$3,411.00 USD total for 28 nights

Sep 30 – Oct 28, 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

$3,152.25 USD total for 28 nights

Sep 9 – Oct 7, 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)
$470/ night(excl. fees & taxes)
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)
$118 – $1,186/ night(excl. fees & taxes)
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)
$136 – $370/ night(excl. fees & taxes)
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)

$6,960.70 USD total for 7 nights

Oct 10 – 17, 2026

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

Sep 26 – Oct 3, 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)

$4,005.58 USD total for 7 nights

Sep 19 – 26, 2026

Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub
Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub
Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub
Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub
Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub

Marathon 3BR w/ Boat is included SEPT - NOV ONLY !!! Hot Tub

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

$1,667.30 USD total for 7 nights

Sep 20 – 27, 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

Sep 11 – 18, 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

$2,457.00 USD total for 7 nights

Sep 7 – 14, 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)

$1,444.00 USD total for 7 nights

Sep 12 – 19, 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)

$1,809.00 USD total for 7 nights

Sep 7 – 14, 2026

Private Pool & Tiki Hut
Aerial2
Home from Street
sunset from our balcony
Enjoy lunch under the Tiki

Tropical Pool Home - Tiki Hut & 60' Dock

2 bedrooms·2 baths
Marathon • Florida

$2,154.00 USD total for 7 nights

Sep 19 – 26, 2026