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Beachfront holiday rental in Islamorada

Find and book unique beachfront homes on Airbnb

Top-rated beachfront accommodation in Islamorada

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

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Home in Key Largo

4.84 out of 5 average rating, 426 reviews

WATER VIEWS ON J. PENNEKAMP Free Kayaks

Ocean views on Largo Sound, totally renovated home with large TV’s, spacious living area, 2 Large Balconies including roof top great for star gazing, all the amenities of home. Free use of kayaks at the house, Kayak John pennekamp state park steps away from front door. 27 foot boat available 4 all water activities Which I captain.Quiet private street close to all keys activities and restaurants. There is a downstairs space that on a very rare occasion is occupied by myself or family member

Guest favourite

Condo in Tavernier

4.89 out of 5 average rating, 247 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 favourite

Condo in Tavernier

4.96 out of 5 average rating, 173 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Guest favourite

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 favourite

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 favourite

Condo in Key Colony Beach

4.96 out of 5 average rating, 194 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.

Guest favourite

Tiny home in Key Largo

4.92 out of 5 average rating, 102 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

Cottage in Islamorada

4.82 out of 5 average rating, 162 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

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. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

Guest favourite

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 favourite

Condo in Tavernier

4.98 out of 5 average rating, 171 reviews

Ocean Views at Ocean Pointe

Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

Guest favourite

Condo in Tavernier

4.94 out of 5 average rating, 110 reviews

BEAUTIFULLY DESIGNED OCEANFRONT CONDO

Enjoy a Tavernier adventure on a private 60-acre oceanfront sanctuary. The condo was recently renovated & is beautifully designed with comfortable, beach chic decor. It offers an abundance of natural light surrounded by windows overlooking lush landscaping and the Atlantic Ocean. Ocean Pointe Suites offers a private sandy beach, a junior Olympic sized pool, a 14-person spa, a boardwalk, a pickleball court, deep-water marina, gazebo, 2 tennis courts & more!

Guest favourite

Cottage in Key Largo

4.89 out of 5 average rating, 300 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

Holiday rentals for every style

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Houses

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Apartments

Convenient locations with everyday essentials

Villas

Luxurious estates for the ultimate escape

Popular amenities for Islamorada beachfront rentals

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

Guest favourite

Home in Marathon

5 out of 5 average rating, 11 reviews

Seaside Sunrise. Newly remodeled waterfront

Guest favourite

Houseboat in Marathon

4.89 out of 5 average rating, 97 reviews

Houseboat Getaway In Marathon

Guest favourite

Rental unit in Key Largo

4.92 out of 5 average rating, 251 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Guest favourite

Home in Key Colony Beach

5 out of 5 average rating, 8 reviews

Key Colony Beach-POOL & DOCK

Guest favourite

Home in Key Largo

4.93 out of 5 average rating, 81 reviews

Tropicasa

Guest favourite

Home in Key Largo

5 out of 5 average rating, 23 reviews

Private 2+ Acre House~Private Beach~Tiki Hut~Dock

Townhouse in Marathon

4.81 out of 5 average rating, 133 reviews

Plunge Pool Villa on Blue Water Lagoon

Guest favourite

Home in Marathon

5 out of 5 average rating, 10 reviews

Casa Marquez

Beachfront home rentals with a pool

Townhouse in Key Largo

4.84 out of 5 average rating, 116 reviews

LIC. MGR. - 2/2 VILLA - OCEANFRONT BEACH RESORT!

Guest favourite

Home in Marathon

4.83 out of 5 average rating, 18 reviews

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

Guest favourite

Home in Marathon

5 out of 5 average rating, 16 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

Guest favourite

Condo in Tavernier

4.87 out of 5 average rating, 138 reviews

Reel Large END Unit in Ocean Point Suites

Guest favourite

Condo in Tavernier

4.97 out of 5 average rating, 60 reviews

Your Happy Place - Oceanfront

Condo in Tavernier

4.89 out of 5 average rating, 152 reviews

2BR - Key Largo Sunshine Getaway

Guest favourite

Condo in Tavernier

5 out of 5 average rating, 16 reviews

Tequila Sunrise

Guest favourite

Villa in Marathon

5 out of 5 average rating, 25 reviews

Sombrero Beach house with dock and tropical pool

Private beachfront home rentals

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 24 reviews

Florida Keys Oceanside Utopia

Guest favourite

Home in Marathon

5 out of 5 average rating, 36 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

Guest favourite

Home in Marathon

5 out of 5 average rating, 21 reviews

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

Guest favourite

Home in Marathon

4.88 out of 5 average rating, 32 reviews

Luxe Waterfront Keys Cottage- with Jacuzzi

Guest favourite

Home in Marathon

4.88 out of 5 average rating, 17 reviews

Viamarhe House-Private beach, Kayak, yard games

Guest favourite

Home in Marathon

5 out of 5 average rating, 70 reviews

New Private 4/3 Single Family - Kayaks & Bicycles+

Condo in Tavernier

4.8 out of 5 average rating, 5 reviews

Island Getaway at Ocean Point

Guest favourite

Home in Key Colony Beach

4.99 out of 5 average rating, 78 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Quick stats about beachfront rentals in Islamorada

Total rentals
200 properties
Nightly prices starting at
$151 NZD before taxes and fees
Total number of reviews
870 reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
120 properties allow pets
Rentals with a pool
180 properties have a pool

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