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Beachfront holiday 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!

Guest favourite

Cottage in Key Largo

4.96 out of 5 average rating, 149 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

Guest favourite

Apartment in Key Colony Beach

4.96 out of 5 average rating, 177 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.

Guest favourite

Flat in Key Largo

4.92 out of 5 average rating, 236 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!

Guest favourite

Houseboat in Key West

4.91 out of 5 average rating, 195 reviews

Key West Luxury Houseboat in Yacht Club - Cold A/C

Beat The Heat! Luxury Houseboat in Private Yacht Club! 15 min from DownTown Key West! Sleeps 6. Brand New Central A/C. 1st level - 2 Queen Bedrooms, 2 Private Ensuite Bathrooms on . 2nd Level - Ocean view Living Room, Full Kitchen, Half Bath. Large, Comfortable Sun Decks for lounging fore and aft on both levels and 40'x15' Rooftop Sun Deck. 15 min from downtown KEY WEST. Located at Stock Island Yacht Club. Panoramic Views from 3rd level sun deck POOL, PRIVATE BEACH, Gym.

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 116 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.”

Guest favourite

Guest house in Key Largo

4.91 out of 5 average rating, 199 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 Cudjoe Key

4.89 out of 5 average rating, 194 reviews

Newly Renovated Oceanside House with Pool

This home is on the Atlantic side of US 1. It is part of Sunrise Beach Resort, a gated community built in 2007 with only 10 other homes. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on one of two balconies, dock or poolside, where you can soak up the sun steps from the house. Breathtaking southwest views of the blue-green ocean and sunsets can be seen from the pool and dock.

Guest favourite

Tiny home in Key Largo

4.89 out of 5 average rating, 142 reviews

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

Modern beach 'Tiny House" cottage on Canal in key largo. Great location for boaters, fisherman and includes 20ft private dock. Great area to kayak, paddle board or fish. Private Tiki hut just steps from the water. Two kayak's included for your use. This is great community which includes private ramp and associotion pool for homeowners. Very close to private beaches only accessible by boat. Well behaved pets allowed

Flat 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

Holiday rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Houses

A space that's all yours, with room for everyone

Popular amenities for beachfront rentals in Key West

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 210 reviews

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

Guest favourite

Townhouse in Marathon

4.83 out of 5 average rating, 125 reviews

Plunge Pool Villa on Blue Water Lagoon

Guest favourite

Home in Key Colony Beach

4.94 out of 5 average rating, 17 reviews

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

Home in Upper Sugarloaf Key

4.75 out of 5 average rating, 61 reviews

Bungalows at Sugarloaf Beach - The Palm

Guest favourite

Home in Key Largo

4.97 out of 5 average rating, 34 reviews

Treetops

Guest favourite

Flat in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

Guest favourite

Home in Marathon

4.9 out of 5 average rating, 10 reviews

4BR Sombrero Beach House on Canal w Dock & Pool

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 26 reviews

Coral Lagoon #23- Private Home with Boat Slip

Beachfront home rentals with a pool

Apartment in Key West

4.84 out of 5 average rating, 44 reviews

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

Guest favourite

Apartment in Key West

5.0 out of 5 average rating, 14 reviews

Premium Ocean View Residence

Guest favourite

Tiny home in Key Largo

4.99 out of 5 average rating, 75 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

Guest favourite

Apartment in Key Largo

4.95 out of 5 average rating, 41 reviews

Paradise at Moon Bay!

Home in Marathon

5.0 out of 5 average rating, 4 reviews

P31 - 11785 5th Ave. Ocean

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 55 reviews

The Paradise 2

Flat in Key West

5.0 out of 5 average rating, 4 reviews

Downtown KeyWest 2Bed Oceanfront

Guest favourite

Flat in Key West

4.94 out of 5 average rating, 17 reviews

Oceanfront Condo in Key West

Private beachfront home rentals

Guest favourite

Apartment in Key West

4.99 out of 5 average rating, 85 reviews

Hidden Beach Duplex, Best Place in Key West

Houseboat in Key West

4.91 out of 5 average rating, 45 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

Apartment in Key West

4.81 out of 5 average rating, 26 reviews

Casa Atlantica: Overlooking the Atlantic shoreline

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Florida Keys Oceanside Utopia

Guest favourite

Home in Key Colony Beach

4.98 out of 5 average rating, 55 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 18 reviews

Direct Oceanfront Private Paradise - Pool/Spa/Dock

Guest favourite

Villa in Marathon

5.0 out of 5 average rating, 22 reviews

Sombrero Beach house with dock and tropical pool

Guest favourite

Cottage in Key Largo

4.98 out of 5 average rating, 55 reviews

Oceanfront Paradise with Amazing View!

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
£118 before taxes and fees

Destinations to explore