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Beachfront vacation rentals in Key West

Find and book unique beachfront homes on Airbnb

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

4.91 out of 5 average rating, 133 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!

Mar. 4 – 11

$1,316 CAD per night

Houseboat in Key West

4.81 out of 5 average rating, 254 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.

Nov. 12 – 19

$582 CAD per night

Guest favourite

Cottage in Key Largo

4.96 out of 5 average rating, 146 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!

Oct. 5 – 12

$546 CAD per night

Cottage in Islamorada

4.85 out of 5 average rating, 128 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.

Mar. 3 – 10

$325 CAD per night

Guest favourite

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

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.

Nov. 8 – 15

$296 CAD per night

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

Oct. 28 – Nov. 4

$539 CAD per night

Guest favourite

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.

Oct. 1 – 8

$944 CAD per night

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 112 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.”

Aug. 22 – 29

$370 CAD per night

Guest favourite

Guesthouse in Key Largo

4.91 out of 5 average rating, 192 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.

Dec. 10 – 17

$314 CAD per night

Home in Cudjoe Key

4.89 out of 5 average rating, 192 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.

Dec. 1 – 8

$650 CAD per night

Guest favourite

Home in Key Largo

4.9 out of 5 average rating, 348 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.

Sep. 13 – 20

$294 CAD per night

Apartment in Key West

4.89 out of 5 average rating, 136 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

Oct. 6 – 13

$861 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Popular amenities for Key West beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Guest favourite

Apartment in Key Largo

4.92 out of 5 average rating, 229 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Jul. 30 – Aug. 6

$374 CAD per night

Guest favourite

Tiny homes in Key Largo

4.89 out of 5 average rating, 137 reviews

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

Feb. 8 – 15

$367 CAD per night

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 208 reviews

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

Jul. 25 – Aug. 1

$645 CAD per night

Guest favourite

Townhouse in Marathon

4.83 out of 5 average rating, 122 reviews

Plunge Pool Villa on Blue Water Lagoon

Oct. 19 – 26

$414 CAD per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 149 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

Nov. 14 – 21

$336 CAD per night

Home in Upper Sugarloaf Key

4.75 out of 5 average rating, 59 reviews

Bungalows at Sugarloaf Beach - The Palm

Oct. 6 – 13

$1,304 CAD per night

Home in Marathon

4.94 out of 5 average rating, 35 reviews

Gorgeous Ocean View Home!

Nov. 5 – 12

$624 CAD per night

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 14 reviews

Private 1 Acre House~Private Beach~Tiki Hut~Dock

Dec. 14 – 21

$1,654 CAD per night

Beachfront home rentals with a pool

Home in Key Colony Beach

4.81 out of 5 average rating, 132 reviews

Waterview from three sides, Cabana Club, 30' Docks

Jan. 13 – 20

$604 CAD per night

Guest favourite

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Sep. 29 – Oct. 6

$405 CAD per night

Condo in Key West

4.84 out of 5 average rating, 44 reviews

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

Jan. 5 – 12

$592 CAD per night

Guest favourite

Apartment in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

Aug. 31 – Sep. 7

$1,070 CAD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

Aug. 31 – Sep. 7

$1,336 CAD per night

Apartment in Key West

5.0 out of 5 average rating, 4 reviews

Downtown KeyWest 2Bed Oceanfront

Jul. 28 – Aug. 4

$742 CAD per night

Guest favourite

Tiny homes in Key Largo

4.98 out of 5 average rating, 66 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

Mar. 27 – Apr. 3

$459 CAD per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

Dec. 14 – 21

$961 CAD per night

Private beachfront home rentals

Houseboat in Key West

4.93 out of 5 average rating, 42 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

Feb. 25 – Mar. 4

$763 CAD per night

Condo in Key West

4.79 out of 5 average rating, 24 reviews

Casa Atlantica: A one bedroom condo on the

Jul. 24 – 31

$740 CAD per night

Guest favourite

Home in Key Colony Beach

4.98 out of 5 average rating, 51 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Oct. 3 – 10

$454 CAD per night

Guest favourite

Condo in Key West

5.0 out of 5 average rating, 28 reviews

Gorgeous Ocean View in Paradise

Aug. 31 – Sep. 7

$875 CAD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 10 reviews

Canal Front, Boat Dock, Updated!

Aug. 8 – 15

$297 CAD per night

Guest favourite

Villa in Marathon

5.0 out of 5 average rating, 19 reviews

Sombrero Beach house with dock and tropical pool

Oct. 12 – 19

$1,516 CAD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Grouper Getaway @ Ocean Isles Fishing Village

Jul. 12 – 19

$331 CAD per night

Guest favourite

Camper/RV in Key Largo

4.98 out of 5 average rating, 42 reviews

paradise point, ocean front /dock/ramp.

Aug. 2 – 9

$319 CAD per night

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
$205 CAD before taxes and fees

Destinations to explore