Beachfront vacation rentals in Monroe County

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Top-rated beachfront rentals in Monroe County

Guests agree: these beachfront homes are highly rated for location, cleanliness, and more.

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Guest favorite

Condo in Tavernier

4.89 out of 5 average rating, 252 reviews

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 38 acres and one side is surrounded by a nature preserve.

Guest favorite

Tiny home in Key Largo

4.96 out of 5 average rating, 102 reviews

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Guest favorite

Cottage in Key Largo

4.96 out of 5 average rating, 157 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 favorite

Houseboat in Tavernier

4.88 out of 5 average rating, 217 reviews

Clean Fully Remodled Houseboat Luxery on the water

Very spacious, Comfortable and "super clean" Houseboat. Rent daily “Baycation” is a 44'x15' triple level upper deck Houseboat completely remodeled. This is an adventure, unlike any hotel room! Live on the water, in an amazing marina, with so much to do you need to come back! Sleep like you never have before, all my guests tell me that! Bonus Lay on the upper deck and see the amazing star ambiance...... This is for everyone......Couples, families & just friends, Its perfect

Guest favorite

Tiny home in Key Largo

4.93 out of 5 average rating, 108 reviews

Oceanfront w/ Dock & Kayak Pirate's Cove Key Largo

1,200 Sq.Ft. w/ outdoor living area and dock Enjoy your Own Private Secluded Retreat, Pirate's Cove 1 Bedroom, w/ 3 Pull-Outs, and one Full Bath, Park Trailer 55 In HDTV in the Living Room, and a 32 In HDTV in the Master Bedroom Full Size Refrigerator King Size Bed in Master Bedroom Regular House Toilet Gas BBQ outside (We do not provide the LP) Wide open water views You have a Community Pool on the next Peninsula. Great Tiki Huts, Stereo, and BBQ Entertainment area outside

Guest favorite

Boat in Islamorada

4.92 out of 5 average rating, 331 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.

Guest favorite

Condo in Key Colony Beach

4.92 out of 5 average rating, 214 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.

Superhost

Houseboat in Key West

4.87 out of 5 average rating, 221 reviews

Key West Luxury Houseboat at Yacht Club Resort

SuperHost 5 years!! ~ 220+ Reviews!! ~ Sleep 6 ~ PRIVATE YACHT CLUB with POOL, PRIVATE BEACH, GYM ~ Only 15 min to Duval St. ~TWO Queen Bedrooms each with Private Full Bathrooms, well equipped FULL Kitchen with Full Sized Appliances ~ Large Sectional Sleeper Sofa and 1/2 Bath on 2nd Level Ocean-View Living Room with Floor-to-Ceiling Windows and 50 inch TV. SUN DECKS on all levels, plus HUGE Rooftop SKY Deck with PANORAMIC Ocean View. GRANITE Countertops Through-out!

Guest favorite

Cottage in Key Largo

4.89 out of 5 average rating, 303 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. Behind the Cottage is Frank out 120 pound Sulcata tortoise.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

Guest favorite

Home in Cudjoe Key

4.92 out of 5 average rating, 156 reviews

Paradise and 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."

Superhost

Tiny home in Key Largo

4.89 out of 5 average rating, 155 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

Guest favorite

Home in Key Colony Beach

4.98 out of 5 average rating, 110 reviews

Super Nov. Savings! Key Colony Beach, Cabana Club

Second Wind is on the 9th Street canal, a beautiful corner lot with exceptional views and ocean breezes. Cabana Club! Dockage for a 20 ft boat. A two-minute walk to Sunset Park in the wonderful community of Key Colony Beach! Open floor plan with cathedral ceiling, large deck with seating for six overlooking the pristine turquoise canal. It is the perfect place for your Florida Keys getaway!