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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, 134 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!

12–19 Dec

$1,199 SGD 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!

23–30 Oct

$494 SGD per night

Guest favourite

Apartment in Key Colony Beach

4.96 out of 5 average rating, 171 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.

1–8 Sep

$471 SGD 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.

4–11 Apr

$270 SGD per night

Guest favourite

Flat in Key Largo

4.92 out of 5 average rating, 231 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!

7–14 Dec

$265 SGD 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.

26 Nov – 3 Dec

$258 SGD per night

Guest favourite

Apartment 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.”

27 Oct – 3 Nov

$320 SGD per night

Guest favourite

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise at 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."

19–26 Dec

$561 SGD per night

Guest favourite

Guest house in Key Largo

4.91 out of 5 average rating, 194 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.

18–25 Mar

$279 SGD per night

Guest favourite

Home in Key Largo

4.9 out of 5 average rating, 349 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.

13–20 Mar

$255 SGD per night

Flat 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

10–17 Dec

$785 SGD per night

Guest favourite

Houseboat in Key West

4.91 out of 5 average rating, 193 reviews

Key West Luxury Houseboat

EXPANSIVE OCEAN VIEW. 2 Queen Bdrms with Large Ensuite Baths on 1st level. Ocean view 2nd Level Living Room and Full Kitchen with half bath. Spacious fore and aft decks. 15 min from downtown KEY WEST. Located at Stock Island Yacht Club. Panoramic Views from 3rd level sun deck POOL, PRIVATE BEACH, Gym.

25 Aug – 1 Sep

$924 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Flats

Convenient locations with everyday essentials

Popular amenities for beachfront rentals in Key West

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Guest favourite

Townhouse in Marathon

4.83 out of 5 average rating, 123 reviews

Plunge Pool Villa on Blue Water Lagoon

11–18 Sep

$314 SGD per night

Guest favourite

Tiny home in Key Largo

4.88 out of 5 average rating, 138 reviews

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

1–8 Jan

$309 SGD 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

19–26 Dec

$563 SGD per night

Guest favourite

Home in Key Colony Beach

5.0 out of 5 average rating, 15 reviews

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

13–20 May

$211 SGD per night

Home in Summerland Key

4.86 out of 5 average rating, 7 reviews

Bungalows at Sugarloaf Beach - Little Hammock

7–14 Dec

$629 SGD per night

Guest favourite

Flat in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

10–17 Oct

$220 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 24 reviews

Coral Lagoon #23- Private Home with Boat Slip

6–13 Mar

$795 SGD per night

Home in Summerland Key

4.89 out of 5 average rating, 19 reviews

Waterfront Captain House with Boat Basin & Ramp!

4–11 Sep

$1,051 SGD 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

19–26 Feb

$537 SGD per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

28 Aug – 4 Sep

$366 SGD per night

Guest favourite

Flat in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

12–19 Aug

$960 SGD per night

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 50 reviews

The Paradise 2

17–24 Aug

$435 SGD per night

Guest favourite

Tiny home in Key Largo

4.99 out of 5 average rating, 68 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

21–28 Mar

$436 SGD per night

Apartment in Key West

4.84 out of 5 average rating, 44 reviews

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

17–24 Apr

$533 SGD per night

Flat in Key West

5.0 out of 5 average rating, 4 reviews

Downtown KeyWest 2Bed Oceanfront

28 Jul – 4 Aug

$668 SGD per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 33 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

29 Mar – 5 Apr

$837 SGD per night

Private beachfront home rentals

Guest favourite

Apartment in Key West

4.99 out of 5 average rating, 84 reviews

Hidden Beach Duplex, Best Place in Key West

4–11 Oct

$884 SGD per night

Houseboat in Key West

4.91 out of 5 average rating, 43 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

4–11 Apr

$716 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 17 reviews

Grouper Getaway @ Ocean Isles Fishing Village

20–27 Oct

$242 SGD per night

Guest favourite

Villa in Marathon

5.0 out of 5 average rating, 19 reviews

Sombrero Beach house with dock and tropical pool

9–16 Mar

$1,315 SGD 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

29 Nov – 6 Dec

$363 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 9 reviews

Oceanfront *PARADiSE* Amazing views, pool, dock

1–8 Mar

$1,384 SGD per night

Guest favourite

Apartment in Key West

5.0 out of 5 average rating, 7 reviews

Premium Ocean View Residence

4–11 Jul

$714 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 15 reviews

Florida Keys Oceanside Utopia

24–31 Oct

$525 SGD 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
$203 SGD before taxes and fees

Destinations to explore