Location

Dates

Guests

Vacation rentals in Key Colony Beach, Florida, United States

Tropical Keys sanctuary steps from private beach.

2 bedrooms·2 baths

Key Colony Beach • Florida

4.89(142 reviews)

$275/ night(excl. fees & taxes)

Condo #15, located on the 2nd floor, offers stunning ocean views and has two screened balconies

Condo #15, located on the 2nd floor, offers stunning ocean views and is depicted in the right building in this photo

Spacious Living Area

Large Heated Pool

Large Heated Pool with loungers

Bird of Paradise: Oceanfront Condo 3 BR, 2 BA with Heated Pool

3 bedrooms·2 baths

Marathon • Florida

5(6 reviews)

$2,173.75 USD total for 7 nights

Sep 19 – 26, 2026

Enjoy a serene walk along the beach, mere steps from your condo.

Large Heated Pool

Enjoy a serene walk along the beach, mere steps from your condo.

Large Heated Pool

Enjoy pool and ocean views from the patio.

Coastal Charm: Steps from the Beach, 2BR/2BA Condo, Pool View

2 bedrooms·2 baths

Marathon • Florida

5(11 reviews)

$1,621.50 USD total for 7 nights

Sep 12 – 19, 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

A View from the Backyard

Hose from the Water (yellow house)

Unobstructed View, 38' Deep Water Dock

Sunset from Yard

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

View of Cove from Backyard

Another Great Sunset

Home from the Water (Yellow)

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

Private Pool &
Tiki Hut

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

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

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

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 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)

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

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)

Plunge into this relaxing salt water pool with 3 waterfalls and spa with pool spillover. Once you get in, you won`t want to get out.

The endless Atlantic Ocean view awaits you. Relaxing is easy in the many chill out spots on the beach.

What could be better than your own private beach 3 levels of balconies give maximum access for viewing the ocean.

Kick back in style with a book and a cocktail while experiencing the amazing ocean breezes.

Take a break from lounging in the sun at the pool cabana while enjoying some snacks.

Casa Feliz Luxury Oceanfront w/Private Beach, Pool

4 bedrooms·4 baths

Marathon • Florida

$8,606.25 USD total for 7 nights

Sep 7 – 14, 2026

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

Keys Escape with Privet Beach & 70' Dock

Keys Escape with Privet Beach & 70' Dock

Keys Escape with Privet Beach & 70' Dock

Keys Escape with Privet Beach & 70' Dock

Keys Escape with Privet Beach & 70' Dock

Keys Escape with Privet Beach & 70' Dock

3 bedrooms·2 baths

Islamorada • Florida

$6,995.00 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)

Brand New - Oceanfront Condo

2 bedrooms·2 baths

Islamorada • Florida

$2,255.00 USD total for 7 nights

Sep 7 – 14, 2026