
Holiday rentals with a pool in Key Colony Beach
Find and book unique homes with a pool on Airbnb
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.

*New Modern*3/2Duplex/37' Dock/Cabana/Kayaks/Bikes
Perfectly situated in KCB w/ 37.5' of dockage on a wide and pristine canal that leads easy access to both the Ocean & the Gulf, our newly listed 1/2 duplex is newly renovated w/ brand new AC, appliances, fixtures, furniture, mattresses, & decors. Featuring 3BR 2BA accommodating up to 8 ppl in a large & open living room & backyard, provided w/ multi-game table, bikes, kayaks, 6-burners grill, 2 mins walk to Sunset park, & Cabana Club access, it is the perfect Florida Keys getaway for your family.

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.

Private Pool! Luxury Paradise Pointe, Pet Friendly
Beautiful Key Colony Beach waterfront duplex with a private pool! Featuring a newly updated, 3/2, spacious 1440 sf home, deep water private boat slip & lift, Tiki Hut w/TV, kayaks, pet friendly, ice machine, bait freezer, large kitchen, Cabana Club, restaurant, and beach access. Family friendly location w/Golf, a playground, and dog park. Sit under the tiki hut, watch the game on the outdoor TV after a day on the water, & grill your catch. Relax on the upper deck sunbathe and enjoy the vistas!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
7 DAY MINIMUM BOOKINGS / MAX 4 PERSONS NAUTI HIDEAWAY - This Nauti Stays Vacation Rental property is a 2-bedroom, 2-bath 2nd level 925 sq ft. condo located in Coco Plum, Marathon. Set in a well-protected, deep canal on the Atlantic, comes with a deep slip (length up to 40 ft) next to pool allowing access to the Atlantic Ocean and Florida Bay. ONSITE boat ramp & trailer (36 ft max) parking! Enjoy a heated or chilled pool after a boat day! Dock has water, power hook ups & fish cleaning station.

NEW PET FRIENDLY Waterfront Single Home-Pool,Beach
NEW VACATION RENTAL. Completely renovated. Open floorplan. New kitchen and bathrooms. New furnishings. Beautiful water views. Game room with pool table. DOGS PERMITTED ($250 FEE PER DOG, 1- 2). YOU MUST TELL ME IF YOU WANT TO BRING A DOG WHEN YOU SUBMIT YOUR REQUEST. Yard with Tiki. Enjoy meals, drinks or shady relaxation. 35 feet of dockage. Cabana Beach and Pool Club included. MUST SIGN KCB AND HOUSE RULES DOCUMENTS WITHIN 48 HOURS OF BOOKING AGE 25 OR OLDER TO BOOK PLEASE

Coastal Key Colony Beach Condo, Oceanfront Complex
Lovely coastal Keys studio condo in Key Colony Beach oceanfront complex with heated pool and private beach. Unit #17 has new beds with memory foam mattress toppers and renovated kitchen with granite countertops stocked with everything needed to cook a complete meal (dishes, cookware, appliances and of course blender, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

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.

Bohemian Beach Bungalow
Cabana Club Access Included! Escape to our newly built 2-bd, 2-bath duplex in KCB, where relaxation meets luxury. Located on the golf course, this stylish home boasts professional decor with modern amenities. While not directly waterfront, ample parking for your boat/trailer. Fully equipped kitchen meets all your culinary needs. Savor effortless access to Havana Jacks, Cabana Club, and Sunset Park, all within walking/biking distance, making this the ultimate Florida Keys retreat

Keys to Paradise
Keys to Paradise has it all. Located in the Gem of the Keys on Key Colony Beach. Just finished building in June 2023. Come & enjoy the beautiful private beach great for kayaking, snorkeling & swimming. White sand beach with lounge chairs for your convenience. This 2+2 has a beautiful ocean view just steps away from the beach. Owners also have ownership at the Cabana Club for you to enjoy drinks by the pool just 2 doors down. Pool is open. 7 day minimum required by City.

P14 - Charming 2 Bedroom, 2 bath waterfront duplex
Welcome to the heart of the Florida Keys! Located in the very desirable Key Colony Beach, this ground level 2 Bedroom, 2 bath duplex boasts ease of access inside and out and is the perfect setting for a tropical vacay-get-away! The other half of the duplex is in our inventory and is listed on our website as P16 (-- ID# - 2245638). - Maximum Occupancy: 4 guests (includes all adults and children of any age) (*children of any age, including infants, count toward occupancy)

Beachside Unit 22 - Private Beach on Atlantic
Unit 22 Details: Main Floor, Walk-in Shower, 2 Queen Beds and Queen Sofa Pull-out, Maximum Occupancy 4 Guests, Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

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.
Popular amenities for Key Colony Beach rentals with a pool
House rentals with a pool

Jan 17-24 2000+tx~Cabana Club~Swim Spa~Fish Equip

Newely Renovated 3/2-private pool/dock/cabana club

Cozi home with dock

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

Aqua Vista~ Luxury Waterfront w Pool & 35' Dock!

Cielo's Del Mar 1 - Pool / Dock / Beach Luxury in KCB

Fun in the Sun!

Waterview from three sides, Cabana Club, 30' Docks
Apartment rentals with a pool

"O" Fish Ally Paradise @Ocean Isle Fishing Village

Marathon 2BR Villa on Lovely Waterfront Resort

1st Floor Condo w Boat Slip, Pool, Adjustable Bed

Oceanside Spacious Studio Escape

2-story condo w/ panoramic bay views and balconies

Paradise found! Sea-Esta Condo beach and pool.

Sandy Toes Approved — Studio Beach Escape

*NEW* Private Beach, pool & fully loaded kitchen
Other holiday rentals with a pool

Florida Keys Retreat, Dock, King bed, Cabana Club

4/2.5 Waterfront home on Key Colony, Pool, Dockage

The Roseate House at Grassy Key Lic. #VACA-25-222

Chiquita Waterfront Canal Home

Castillo Del Mar- Ocean access from your backyard

Searenity Vacation Rental! Pool, Tiki Hut, Dockage

Canal/Dock - Cabana Club - Pickleball - Remodeled

Razz's Retreat at KCB!
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 | £233 | £269 | £283 | £231 | £206 | £215 | £224 | £207 | £177 | £178 | £191 | £227 |
| 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 |
Quick stats about holiday rentals with a pool in Key Colony Beach

Total holiday rentals
Explore 450 holiday rentals in Key Colony Beach

Nightly prices starting at
Key Colony Beach holiday rentals start at £59 per night before taxes and fees

Verified guest reviews
Over 15,270 verified reviews to help you choose

Family-friendly holiday rentals
380 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 160 rentals that welcome pets

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
450 of Key Colony Beach holiday rentals include wifi 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!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Pet-friendly rentals Key Colony Beach
- Beach house rentals Key Colony Beach
- Flat rentals Key Colony Beach
- Fitness-friendly rentals Key Colony Beach
- Family-friendly rentals Key Colony Beach
- Rentals with a kayak Key Colony Beach
- Rentals with a patio Key Colony Beach
- Rentals with breakfast Key Colony Beach
- Beachfront rentals Key Colony Beach
- Rentals with a firepit Key Colony Beach
- Apartment rentals Key Colony Beach
- Waterfront rentals Key Colony Beach
- Rentals with a hot tub Key Colony Beach
- Rentals with beach access Key Colony Beach
- Hotel rooms Key Colony Beach
- Beach apartment rentals Key Colony Beach
- Rentals with outdoor seating Key Colony Beach
- House rentals Key Colony Beach
- Townhouse rentals Key Colony Beach
- Rentals with a washing machine and dryer Key Colony Beach
- Rentals with pools Monroe County
- Rentals with pools Florida
- Rentals with pools United States
- Everglades National Park
- Sombrero Beach
- Smathers Beach
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Cannon Beach
- Far Beach
- Sea Oats Beach
- Conch Key
- Theater of the Sea
- Long Key State Park
- Long Beach
- Horseshoe Beach
- EAA Air Museum
- Bahia Honda State Park
- Windley Key Fossil Reef Geological State Park
- Sandspur Beach
- Keys' Meads




