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Beachfront vacation rentals in Key West

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Top-rated beachfront rentals in Key West

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Cottage in Cudjoe Key

4.9 out of 5 average rating, 136 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

Houseboat in Key West

4.81 out of 5 average rating, 255 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Condo in Key Colony Beach

4.97 out of 5 average rating, 175 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Cottage in Islamorada

4.84 out of 5 average rating, 133 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Apartment in Key Largo

4.92 out of 5 average rating, 234 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

Condo in Key West

4.99 out of 5 average rating, 84 reviews

Hidden Beach Duplex, Best Place in Key West

Go to sleep and wake up smiling listening to the waves. Just 3 blocks from Duval Street; this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort. This is an extraordinary condo on an extraordinary property. This is nicest unit of 3 for rent at Hidden Beach. If you are discerning, this really is best place place to stay in Key West.

Condo in Key Colony Beach

4.91 out of 5 average rating, 114 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with 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.”

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise and Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

Guesthouse in Key Largo

4.91 out of 5 average rating, 196 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

Home in Key Largo

4.89 out of 5 average rating, 352 reviews

Your Keys Getaway!

Beautiful two bedrooms, 1 bath Keys Home fully renovated interior in a quiet residential neighborhood. Large breeze veranda for open air meals and relaxation. Large fence yard for sunbathing or playing around. Close to restaurants, shopping center, major hospital, beaches, parks and water sport activities. Perfectly located between Key Largo and Islamorada. Once you've been here you will want to come back.

Apartment in Key West

4.89 out of 5 average rating, 137 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

Houseboat in Key West

4.91 out of 5 average rating, 43 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

Romantic getaway on the sea with panoramic views of the ocean. Capture each sunrise and sunset on board this one-of-a-kind, floating vacation suite. Luxurious amenities include a full en suite bath with a rainfall shower head, heated water, A/C, kitchenette, electricity, wi-fi, and even a projector in case you want to "Netflix & chill." Snorkel gear, kayak, and magic included.

Vacation rentals for every style

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Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Key West beachfront rentals

Free parking on premises

Air conditioning

Beachfront home rentals with a pool

Cottage in Key Largo

4.96 out of 5 average rating, 147 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Condo in Tavernier

4.96 out of 5 average rating, 160 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Condo in Key West

4.84 out of 5 average rating, 44 reviews

Ocean front 1BR/1BA Suite w/ kitchen & living rm

Condo in Key West

4.91 out of 5 average rating, 11 reviews

Ocean View Residence

Apartment in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

Home in Key Largo

5.0 out of 5 average rating, 52 reviews

The Paradise 2

Home in Upper Sugarloaf Key

4.88 out of 5 average rating, 48 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Apartment in Key West

5.0 out of 5 average rating, 4 reviews

Downtown KeyWest 2Bed Oceanfront

Beachfront home rentals with a hot tub

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Condo in Tavernier

4.88 out of 5 average rating, 229 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Condo in Tavernier

4.93 out of 5 average rating, 137 reviews

It's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba

Home in Key Colony Beach

4.81 out of 5 average rating, 134 reviews

Waterview from three sides, Cabana Club, 30' Docks

Condo in Tavernier

4.98 out of 5 average rating, 143 reviews

Ocean Views at Ocean Pointe

Townhouse in Marathon

4.83 out of 5 average rating, 124 reviews

Plunge Pool Villa on Blue Water Lagoon

Condo in Tavernier

4.97 out of 5 average rating, 159 reviews

Serenity In The Sun

Condo in Tavernier

4.91 out of 5 average rating, 111 reviews

500 Burton Drive Tavernier, Key Largo

Pet-friendly beachfront home rentals

Tiny home in Key Largo

4.88 out of 5 average rating, 139 reviews

Modern beach tiny house/Tiki hut/ boat dock 20ft

Home in Tavernier

4.87 out of 5 average rating, 208 reviews

Clean Houseboat w/ Great Wi-Fi,Luxury on the water

Home in Key Colony Beach

5.0 out of 5 average rating, 15 reviews

Coral House: 2/2 Waterfront in KCB w/ King Beds

Home in Key Largo

4.97 out of 5 average rating, 32 reviews

Treetops

Home in Marathon

5.0 out of 5 average rating, 25 reviews

Coral Lagoon #23- Private Home with Boat Slip

Apartment in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

Home in Marathon

4.94 out of 5 average rating, 35 reviews

Gorgeous Ocean View Home!

Home in Summerland Key

4.89 out of 5 average rating, 19 reviews

Waterfront Captain House with Boat Basin & Ramp!

Quick stats about beachfront rentals in Key West

Total rentals
90 properties
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Rentals with a pool
80 properties have a pool
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
$150 before taxes and fees

Destinations to explore