
Vacation rentals with a pool in Key Colony Beach
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Key Colony Beach

Total vacation rentals
Explore 450 vacation rentals in Key Colony Beach

Nightly prices starting at
Key Colony Beach vacation rentals start at ﺩ.ﺇ 588 per night before taxes and fees

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Over 16,720 verified reviews to help you choose

Family-friendly vacation rentals
370 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 160 rentals that welcome pets

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wi-Fi availability
450 of Key Colony Beach vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Key Colony Beach rentals

4.8 Average rating
Key Colony Beach stays are highly rated by guests—averaging 4.8 out of 5!
Top-rated rentals with a pool in Key Colony Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Gorgeous 3 Bdrm Home w/ private pool, 60' dockage
🌴 4 Ever Big Sky – Coastal Luxury Retreat | Private Pool + 60’ Dockage | Key Colony Beach, FL | 3 Bedroom plus bonus Florida Room/ 3 Bath Welcome to 4 Ever Big Sky, a sophisticated waterfront escape where modern coastal design meets effortless Florida Keys living. Ideally located on prestigious 12th Street in Key Colony Beach, this beautifully curated home features a private pool, 60 feet of dockage, and an unforgettable outdoor oasis designed for both relaxation and entertaining. ✨ The Expe

Waterfront House with 37 ft Dock & Cabana Club
Right in the middle of the action between Miami and Key West. This 2/2 house has been nicely renovated and furnished with new stainless kitchen appliances and a gorgeous granite countertop. Comfortable outside/inside living space perfect for a getaway in paradise. Walk out to the porch and backyard, and you will be engulfed by the beauty of the sunset views while lying on the cozy hammock. It features lots of outdoor entertaining: fishing, paddling, BBQ or just plain hanging out in the shade.

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK
The Snapper House is a spacious 3/2.5 bed/bath duplex with 45' of canal dock frontage, also Includes the Cabana Club with large pool (food/drinks for purchase) and ocean facing beach. Awning extends to dock from sliding doors. TV package includes 100+ channels Each bedroom and living room has a full size flat screen TV. For best WIFI reception, an extender is available and should be used when in the back bedrooms, it's name is the same as the main house with an "ext" at the end (same pw).

Salt & Seaglass. Screen Porch, Dock, Pool Club!
This Key Colony Beach home is a welcoming, modern canal-front duplex home provides a relaxing and comfortable atmosphere for your vacation in the Florida Keys! The home features 2 large bedrooms and 2 bathrooms, a modern kitchen with large island and granite counter tops, a master bedroom with private bathroom and modern, plank flooring tile throughout the home. Enjoy the relaxing 9 X 20 ft porch & comfortable furniture. Outside: Lounge chairs & other seating, a kayak, a 37 foot dock

Entire private two family water front home.
Forget your worries in this spacious and serene space. This is a great option for large multi-generational families that want to be in two separate areas of a full home. This is a full two family home with separate entrances. Enjoy 75 feet of waterfront with a concrete seawall, davits, a fish cleaning station, and direct ocean and bay access via nearby Vaca Cut. The home offers full privacy, a private heated and chilled pool in the heart of Key Colony Beach; the entire home is yours!

Exquisite Oceanfront Paradise - Key Colony Beach
Stunning direct ocean views. Everything is brand new in this gorgeous condo with comfy king bed and fully equipped kitchen with full-size appliances and everything you need to cook and serve meals. Fast, free, reliable WiFi, and SmartTV to enjoy your favorite movies and shows. Heated pool and private sandy beach just steps away. Sunset Park next door is perfect for catching beautiful nightly sunsets. Centrally located to awesome Keys adventures just a few miles drive from the condo.

Waterfront Home 37.5-ft dock, Cabana Club Included
Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

The Islander 3BR Pool Oasis in Key Colony- KCB#1
5-Star Luxury 3-Bedroom Pool Home in Key Colony Beach Welcome to your dream getaway! This stunning 3-bedroom, 5-star rated home is located in the exclusive island community of Key Colony Beach—one of the most unique and charming destinations in the world. INCLUDED is a private club with a Private Club with a Sandy Beach,Jacuzzi and Olympic Heated Pool..Enjoy the best of the Florida Keys with your own private, luxury heated chilled pool, deep water dock. Small pets allowed.

P67 - Spacious 3 bedroom 4 bath with private pool,
This lovely two story duplex offers 3 bedroom, 4 bathrooms and abundant living space on both levels. The lower level offers a second master bedroom with king size bed and private bathroom. This home also comes with access to the Cabana Club; its private beach, large pool, bar and grill. Key Colony Beach offers a par 3, nine-hole golf course, public tennis courts, Sunset Park, several restaurants, coffee shop, clothing boutiques and charter fishing center.

Pet Friendly Half Duplex Pool Home with Boat Slip
Want a spacious home with private pool and dock? You have found it! On a deep water canal. Enough dock space for a 37' boat. Enjoy your private heated pool or lounge in the shade or sun. Water views from EVERY room (canal in back, pond with fountains in front). Easy walking to restaurants, shops, golf course, park, playground and entertainment. YOU MUST AGREE TO THE CITY'S RULES, IF YOU BOOK. Pool heater optional. $50/night or $250/week

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

*New* Turtles Pace-Private Beach
Discover the perfect getaway in this beachfront condo in Key Colony Beach, FL. With direct access to a private beach, you’ll enjoy breathtaking ocean views and endless relaxation. This condo features modern amenities, a fully equipped kitchen, and comfortable living spaces. Whether you’re soaking up the sun on the beach or exploring local attractions, this is the ultimate coastal escape. Don't miss the chance to experience paradise!
Popular amenities for Key Colony Beach rentals with a pool
House rentals with a pool

Your Key Colony Beach Paradise Awaits!

Private Pool! Luxury Paradise Pointe, Pet Friendly

“La casa azul” step 3’ to a private pool

KeyColony,4 Bedroom, Pool, 40'Dock, Quick Vaca Cut

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

Lux Waterfront: Dock, Volleyball, Putt Putt, More

KCB Tiki Hut Oasis: 37.5' Dock + Cabana Club!

Modern Island Luxury | 4 En-Suite Masters, 6 BA, P
Condo rentals with a pool

Beachside Unit 33-Private Tropical Beach Plus Pool

Slip, Private Ramp, Pool, Trailer Parking, Freezer

Waterfront Condo, daily housekeeping & breakfast!

Paradise found! Sea-Esta Condo beach and pool.

Private Beach in Marathons Key Colony Beach

*NEW* Private Beach, pool & fully loaded kitchen

Anglers Paradise ~ Waterfront Condo with Boat Slip

Peaceful, Newly Renovated Condo With Boat-slip.
Other vacation rentals with a pool

Castillo Del Mar- Ocean access from your backyard

Cabana Club Privileges! Paddleboards, Bikes, Kayak

Private Pool, Paddleboards, Bikes & Lots of Games!

DOCK-Beach Club-Tiki Hut-Screened Porch-East Yard

Lagoona-Matata

Beach House in Marathon with Amazing Backyard!

*NEW!*Paradise Point~VIEWS!~Open Water~Dock~Pool!

Welcome to Paradise, Private Pool, SUPs, Kayak!
When is the best time to visit Key Colony Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 1,322 | ﺩ.ﺇ 1,528 | ﺩ.ﺇ 1,528 | ﺩ.ﺇ 1,227 | ﺩ.ﺇ 1,105 | ﺩ.ﺇ 1,190 | ﺩ.ﺇ 1,109 | ﺩ.ﺇ 1,028 | ﺩ.ﺇ 878 | ﺩ.ﺇ 896 | ﺩ.ﺇ 1,028 | ﺩ.ﺇ 1,285 |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
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- Everglades National Park
- Sombrero Beach
- Smathers Beach
- Calusa Campground
- Bahia Honda State Park
- Robbies Marina Of Islamorada
- Seven Mile Bridge
- Theater of the Sea
- Key Largo Kampground And Marina
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