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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

4.9 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

€ 894 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

€ 372 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

€ 221 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

€ 201 per night

Guest favourite

Flat in Key Largo

4.92 out of 5 average rating, 230 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

€ 207 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.

1–8 Jan

€ 577 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.

22–29 Mar

€ 505 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."

25 Sep – 2 Oct

€ 390 per night

Guest favourite

Guest house in Key Largo

4.91 out of 5 average rating, 193 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.

12–19 Mar

€ 213 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

€ 203 per night

Guest favourite

Boat in Miami

4.98 out of 5 average rating, 695 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.

25 Jul – 1 Aug

€ 143 per night

Guest favourite

Apartment in Palmetto Bay

4.89 out of 5 average rating, 198 reviews

Bright Modern Studio Apartment

Find yourself at this slick Studio Apartment professionally designed, top of the art appliances with a unique modern touch. Based in a quiet and peaceful neighborhood. Located close to Downtown Miami and also to The Florida Keys. Nearby shoppings centers, restaurants and supermarkets. All you need to enjoy a charming getaway.

22–29 Oct

€ 117 per night

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Houses

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

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

19–26 Dec

€ 423 per night

Townhouse in Duck Key

4.83 out of 5 average rating, 130 reviews

Vibrant Beachfront Villa

13–20 Oct

€ 489 per night

Guest favourite

Townhouse in Marathon

4.83 out of 5 average rating, 123 reviews

Plunge Pool Villa on Blue Water Lagoon

11–18 Sep

€ 253 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

€ 246 per night

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 149 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

20–27 Dec

€ 495 per night

Guest favourite

Apartment in Miami

4.9 out of 5 average rating, 151 reviews

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

16–23 Sep

€ 433 per night

Townhouse in Key Largo

4.85 out of 5 average rating, 104 reviews

Sunrise Escape - Ocean Front Villa - Sleeps 10

30 Jan – 6 Feb

€ 992 per night

Apartment in Miami

4.82 out of 5 average rating, 211 reviews

Sea-view balcony, Free Park, Kitchen, Washer-Dryer

27 Sep – 4 Oct

€ 266 per night

Beachfront home rentals with a pool

Guest favourite

Apartment in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

28 Jan – 4 Feb

€ 570 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

13–20 Nov

€ 252 per night

Home in Key Colony Beach

4.81 out of 5 average rating, 132 reviews

Waterview from three sides, Cabana Club, 30' Docks

19–26 Dec

€ 467 per night

Guest favourite

Apartment in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

3–10 Oct

€ 394 per night

Guest favourite

Apartment in Tavernier

4.99 out of 5 average rating, 102 reviews

Ocean View Corner Penthouse | Ocean Pointe 5416

6–13 Feb

€ 625 per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

25 Sep – 2 Oct

€ 278 per night

Guest favourite

Tiny home in Key Largo

4.99 out of 5 average rating, 67 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

27 Jan – 3 Feb

€ 318 per night

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 50 reviews

The Paradise 2

4–11 Sep

€ 394 per night

Private beachfront home rentals

Guest favourite

Cottage in Key Largo

4.89 out of 5 average rating, 272 reviews

Cottage By The Sea

15–22 Nov

€ 256 per night

Houseboat in Key West

4.93 out of 5 average rating, 42 reviews

The Crystalmarine Suite – Rustic Luxury on the Sea

7–14 Nov

€ 519 per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 15 reviews

Florida Keys Oceanside Utopia

11–18 Jan

€ 433 per night

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

€ 642 per night

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 46 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

20–27 Oct

€ 1,131 per night

Home in Cudjoe Key

4.87 out of 5 average rating, 45 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

1–8 Dec

€ 797 per night

Guest favourite

Home in Duck Key

5.0 out of 5 average rating, 31 reviews

Private Pool Tropical Oasis - Centrally Located

10–17 Nov

€ 623 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

€ 1,044 per night

Destinations to explore