
Beachfront holiday rental in Key West
Find and book unique beachfront homes on Airbnb
Quick stats about beachfront rentals in Key West

Total holiday rentals
Explore 90 holiday rentals in Key West

Nightly prices starting at
Key West holiday rentals start at $227 NZD per night before taxes and fees

Verified guest reviews
Over 1,800 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Holiday rentals with a pool
90 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
90 of Key West holiday rentals include Wi-Fi access

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

4.7 Average rating
Key West stays receive an average rating of 4.7 out of 5 from guests
Top-rated beachfront accommodation in Key West
Guests agree: These beachfront homes are highly rated for location, cleanliness and more.

*NEW* Private Beach, pool & fully loaded kitchen
Escape to paradise in our brand new, beautifully furnished Sun Life Vacation Homes beachfront oasis in the heart of Key Colony Beach, Florida, (some still call it Marathon). This luxurious two-bedroom, two-bathroom condominium invites you to experience the ultimate coastal retreat with private beach & pool access, tiki huts and BBQ grills. Come and experience the ultimate beachfront getaway at our Sun Life Vacation Homes, Key Colony Beach Club vacation rental. We recommend all guests purchas

Bright Cheery Condo, Ocean Views in Key Colony
Beautifully renovated condo in Key Colony Beach. with one king bed, well equipped kitchen with full-size appliances & everything you need to cook and serve meals. New A/C for great cooling. Renovated bathroom with walk-in shower, plenty of counter space and storage. Free & reliable WiFi with a private back balcony with chairs and table. Enjoy the heated pool & private sandy beach just steps away from your condo door. Sunset Park is next door, great for catching beautiful Florida Keys sunsets.

Private Beach in Marathons Key Colony Beach
Atlantic Ocean location with a beautiful ocean view. The beach is private for sunbathing, fishing, diving, and snorkeling. The sea life off the beach is abundant. Watching the boats come in and out of Vaca Cut is very cool. In addition to the onsite pool there is a Tiki Hut, beachside barbecue area, and a beautiful grass lawn. Being on the third floor offers beautiful ocean views. Please see my host guidebook for detailed info on a few of the local attractions including fav restaurants.

Oceanside home 111, dock,kayaks,bikes,pool,fishing
This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Family Suite at Sugarloaf Key Hotel (Pet Friendly)
Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

P01 - New 3 bed, 3 bath with private pool
This beautiful new home offers 3 bedrooms, 3 baths and a comfortable open floorplan. Additionally, this property boasts and abundance of fabulous outdoor living space and is ideally located minutes from Coco Plum Beach. - Maximum Occupancy: 6 guests (includes adults and children of any age) (*children of any age, including infants, count toward occupancy) - No day guests or visitors allowed above the advertised max. occupancy. - Parking: 3 vehicle max - 3 bedroom/3 bathroom

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Beachside Unit 33-Private Tropical Beach Plus Pool
Unit 33 Details: Second Floor, Walk-in shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and 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.”

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Key West Condo with Balcony Ocean View
Enjoy beautiful views of the Atlantic Ocean while enjoying a private balcony. Newly re-modeled kitchen. Air conditioning and ceiling fans located in every room. Amenities include pool, hot tub, and tennis courts. Just a few steps across the street in Smathers Beach which offers beach chairs, umbrellas, paddle boards, kayaks and sailboats available for rent. Two vehicles max. NO TRAILERS of any kind allowed to park on property.

*NEW* Penthouse-Beach Front
Live the island dream in this stunning 2 Bed | 2 Bath Penthouse Condo perfectly situated in the heart of Key Colony Beach, Florida. Perched on the top floor, this coastal retreat offers sweeping, unobstructed views of the Atlantic Ocean and direct beach access—your private paradise in the Florida Keys. The primary suite includes a private bath and sliding doors that open directly to the balcony, letting you enjoy amazing Sunsets.
Popular amenities for Key West beachfront rentals
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

Coco Plum Beach Paradise w Heated Pool & Boat Slip

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Key West Luxury Houseboat at Yacht Club Resort

New Private 4/3 Single Family - Kayaks & Bicycles+

SeaEsta! Bring your boat & 1 block to the beach!

Vibrant Beachfront Villa
Beachfront home rentals with a pool

Seaside Villa~ Charming Beachfront Condo w/ Pool!

Grouper Getaway @ Ocean Isles Fishing Village

Galleon Resort - Walk to Duval & Mallory Square!

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Marathon 2BR Waterfront property on Resort

Canal/Dock - Cabana Club - Pickleball - Remodeled

Beach Front

2 Bdrm Oceanfront Complex Private Beach & Pool
Private beachfront home rentals

Spectacular 2BR Oceanfront Dog Friendly | Dock

#7 Oceanfront 4Bed 3Bath Pool Home

Powell Family Resort

Stunning tropical Ocean view condo

Charming Beach House directly ON the beach

Paradise awaits.

Beachfront Condo on Coco Plum Beach w/heated pool

Florida Keys Getaway w/ Stunning Ocean Views
When is the best time to visit Key West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $1,091 NZD | $1,159 NZD | $1,116 NZD | $980 NZD | $915 NZD | $898 NZD | $812 NZD | $757 NZD | $744 NZD | $976 NZD | $990 NZD | $1,046 NZD |
| 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 |
Destinations to explore
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- Beachfront rentals Monroe County
- Beachfront rentals Florida
- Beachfront rentals United States
- Sombrero Beach
- Smathers Beach
- Bahia Honda State Park
- Ernest Hemingway Home & Museum
- Seven Mile Bridge
- Fort Zachary Taylor Historic State Park
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Key West Lighthouse Museum
- Boca Grande Key
- Mel Fisher Maritime Museum
- Truman Little White House
- Key West Aquarium
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- Things to do Florida
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