Waterfront vacation rentals in Key West

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Key West

Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Townhouse in Marathon

4.97 out of 5 average rating, 158 reviews

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

*Currently the seawall repair is not affecting our side of the property, our view is unobstructed and not affected. Also, our marina is 100% open and operational should you need to rent a slip during your stay Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house

Guest favorite

Cottage in Cudjoe Key

4.92 out of 5 average rating, 99 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Guest favorite

Condo in Tavernier

4.86 out of 5 average rating, 268 reviews

Condo in the Keys, Peaceful ocean view retreat!

Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Superhost

Townhouse in Duck Key

4.82 out of 5 average rating, 156 reviews

Villa 5020 on Duck Key BOAT SLIP available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

Guest favorite

Condo in Tavernier

4.96 out of 5 average rating, 174 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 favorite

Rental unit in Key Largo

4.92 out of 5 average rating, 132 reviews

2/1 Oceanfront Apartment with Dockage

The Seaside Vista is a luxurious ocean front retreat located in Key Largo. Only 1 hour from Miami International Airport, we are located in the heart of the fishing and diving areas of the Florida Keys. From great dining, to water sports, to eco tours, to parasail, to museums, shopping and beaches, allow us to be your base for all of your Florida Keys activities. Freshly remodeled , enjoy our little piece of paradise...minutes from all that the Upper Keys has to offer. MC Permit #: 21302180

Superhost

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 favorite

Condo in Key Colony Beach

4.96 out of 5 average rating, 240 reviews

Amazing Ocean Front Views Key Colony Beach

Ocean front Florida Keys Studio Condo in Key Colony Beach with private balcony, heated pool and sandy beach. Continental Inn Unit #40 is a studio condo with a tropical interior featuring 2 queen beds and kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Relax on the back balcony and enjoy sunsets from Sunset Park right next door. Private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Guest favorite

Cottage in Little Torch Key

4.9 out of 5 average rating, 155 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Guest favorite

Condo in Key West

4.89 out of 5 average rating, 140 reviews

Aruba - Downtown Waterfront 2/2 Dock, Pool, Pet

Time to relax! Bring your family & friends to this 1200 sqft Waterfront home. Boat slips available on site with commercial ice machine, fish cleaning station and BBQ grills. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Historic Seaport, Hemingway House, etc. On-site amenities: heated pool, boat slip, tiki bar & grills, parking, secure keyless entry, & private elevator. Large Park adjacent with tennis courts. 10min from airport (EYW).

Superhost

Houseboat in Big Pine Key

4.74 out of 5 average rating, 141 reviews

2 Bedroom Aqualodge # 11 Grouper

This 2 Bedroom Aqualodge is an adorable accommodation in the Old Wooden Bridge Resort and Marina. You are able to enjoy the resort amenities during your stay. Beautiful Salt Water pool, Fish Cleaning Stations. Renters can also bring their boat or rent a boat from OWB at an additional fee. There is NO Swimming in the Marina Boat Basin. There is a beautiful salt water pool to use for your swimming pleasure. This is a marina with houseboats and rental boats in the slips.

Guest favorite

Condo in Tavernier

4.98 out of 5 average rating, 172 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.