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Beachfront holiday rentals in Monroe County

Find and book unique beachfront homes on Airbnb

Top-rated beachfront rentals in Monroe County

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!

2–9 Mar

$1,210 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!

8–15 Oct

$498 SGD 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.

9–16 Mar

$534 SGD per night

Cottage in Islamorada

4.85 out of 5 average rating, 127 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.

20–27 Nov

$272 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.

24–31 Oct

$260 SGD per night

Guest favourite

Apartment 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.

29 Oct – 5 Nov

$475 SGD per night

Guest favourite

Townhouse in Duck Key

4.94 out of 5 average rating, 142 reviews

2B/2.5B Villa at Village at Hawks Cay with Spa

Our Villa is located between Islamorada and Marathon Key on Duck Key at the Village of Hawks Cay; one of the most desirable locations in the Florida Keys. This is at Mile Marker 61. With ocean views, high-end finishes, comfy beds and plenty to do in the surrounding areas, the Villa offers something for everyone. There is an in-ground splash pool located on the patio. It is not a hot tub but reaches a maximum temperature of 104 degrees for those desiring heat.

15–22 Aug

$470 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."

11–18 Jan

$563 SGD per night

Guest favourite

Guest house in Key Largo

4.91 out of 5 average rating, 191 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.

5–12 Oct

$282 SGD per night

Guest favourite

Cottage in Key Largo

4.89 out of 5 average rating, 271 reviews

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals Less than 2 miles to Bakers Cay.

8–15 Sep

$327 SGD per night

Guest favourite

Home in Key Largo

4.9 out of 5 average rating, 347 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.

28 Sep – 5 Oct

$257 SGD per night

Guest favourite

Boat in Miami

4.98 out of 5 average rating, 694 reviews

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Key Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

18–25 Jun

$190 SGD per night

Holiday rentals for every style

Get the amount of space that is right for you

Houses

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

Villas

Luxurious estates for the ultimate escape

Flats

Convenient locations with everyday essentials

Popular amenities for beachfront rentals in Monroe County

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 208 reviews

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

29 Oct – 5 Nov

$568 SGD per night

Guest favourite

Flat in Key Largo

4.92 out of 5 average rating, 229 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

17–24 Jul

$360 SGD per night

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 149 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

21–28 Aug

$230 SGD per night

Townhouse in Duck Key

4.83 out of 5 average rating, 130 reviews

Vibrant Beachfront Villa

3–10 Feb

$815 SGD per night

Guest favourite

Tiny home in Key Largo

4.89 out of 5 average rating, 137 reviews

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

20–27 Jan

$318 SGD per night

Guest favourite

Townhouse in Marathon

4.83 out of 5 average rating, 122 reviews

Plunge Pool Villa on Blue Water Lagoon

22–29 Apr

$532 SGD per night

Guest favourite

Apartment in Miami

4.9 out of 5 average rating, 151 reviews

ICON 2B/2B Skyline Free Pool, Spa, HotTub

22–29 Sep

$578 SGD per night

Townhouse in Key Largo

4.85 out of 5 average rating, 104 reviews

Sunrise Escape - Ocean Front Villa - Sleeps 10

13–20 Dec

$1,078 SGD per night

Beachfront home rentals with a pool

Guest favourite

Apartment in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

31 May – 7 Jun

$290 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

30 Aug – 6 Sep

$375 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

22–29 Aug

$323 SGD per night

Guest favourite

Apartment in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

29 Sep – 6 Oct

$581 SGD per night

Home in Key Colony Beach

4.81 out of 5 average rating, 132 reviews

Waterview from three sides, Cabana Club, 30' Docks

17–24 Feb

$542 SGD per night

Guest favourite

Campervan/Motorhome in Key Largo

4.99 out of 5 average rating, 144 reviews

NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!

21–28 Feb

$496 SGD per night

Guest favourite

Tiny home in Key Largo

4.94 out of 5 average rating, 125 reviews

A place to make your dreams come true

14–21 Sep

$328 SGD per night

Guest favourite

Tiny home in Key Largo

4.98 out of 5 average rating, 65 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

13–20 Mar

$400 SGD per night

Private beachfront home rentals

Guest house in Key Largo

4.87 out of 5 average rating, 377 reviews

Guesthouse Tropical Paradise Beach sunset fishing

3–10 Jul

$338 SGD per night

Guest favourite

Houseboat in Key West

4.96 out of 5 average rating, 128 reviews

Beautiful Houseboat in Key West

25 Mar – 1 Apr

$796 SGD per night

Houseboat in Key West

4.93 out of 5 average rating, 41 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

1–8 Oct

$722 SGD per night

Guest favourite

Apartment in Key West

4.96 out of 5 average rating, 76 reviews

Hidden Beach unit 1 The Perfect Place to stay

28 Nov – 5 Dec

$849 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

26 Apr – 3 May

$867 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sep

$1,122 SGD per night

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 45 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

5–12 Feb

$1,285 SGD per night

Home in Marathon

4.94 out of 5 average rating, 35 reviews

Gorgeous Ocean View Home!

10–17 Feb

$567 SGD per night

Destinations to explore