Holiday houses in Key West

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Top-rated holiday rentals in Key West

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

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Superhost

Campervan/RV in Key Largo

4.78 out of 5 average rating, 18 reviews

A motorhome in paradise

Este lugar es realmente único. Hermoso acogedor tiene todo lo necesario para pasar unas buenas vacaciones piscina parque marina Area de descanso a la orilla del mar vistas hermosas de la caída del sol Area para lavar cerca de supermercados y restaurantes sin duda alguna un hermoso lugar Es un CAMPO DE TRAILER rodeado de naturaleza NO es un hotel 5 estrellas ni nada parecido Si de verdad te gusta la aventura y sentir la naturaleza aire mar sol lindas vistas este es un lugar perfecto No mascota

Guest favourite

Campervan/RV in Key Largo

4.96 out of 5 average rating, 113 reviews

Paradise Casa Bayfront sunsets,pool,King bed ,dock

Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

Guest favourite

Home in Key West

5 out of 5 average rating, 11 reviews

Key Lime Retreat

Weekly Treat! Downtown vacation experience for entire family. Located in the hearth of Historic Seaport location in Key West. Conveniently walking distance to Duval St shopping, offices, entertainment, restaurants, bars, and everything Key West has to offer. There is not much to say about this condo, The location talks for itself! It’s a must have Key West experience on a quite gated community just steps away from Duval St. It’s a true Gem to experience the Key West living to the fullest extend.

Guest favourite

Home in Cudjoe Key

4.83 out of 5 average rating, 30 reviews

Yellow Home Free Pontoon Rental! See details

If you book your stay for the days shown below March 30th - April 15th, 2025 April 23rd - May 3rd, 2025 May 17th - May 31st, 2025 June 6th - June 13th, 2025 Receive a free 2 day boat rental for a week reservation, 1 day for a 3 days or more reservation. Please reach out before booking for boat availability. Beautiful 3 bedroom 2 bath home nestled off of US 1. Kayaks included with the rental. Private heated pool and deck with a view of the Atlantic Ocean. Boat dockage available with parking.

Guest favourite

Holiday home in Key Largo

4.94 out of 5 average rating, 116 reviews

Ocean Shores Villa 3 with pool and boat slip

This centrally located boater's paradise is the perfect place to relax. Walk to restaurants, cook in kitchen or grill downstairs. With only 4 units in the building the guests have half an acre of waterfront entertainment (boat slip, Kayaks, Bikes, Hammock and Pool). 32ft Dock Slip and Trailer Parking are included in the rental. Relaxing Balcony that looks down the Ocean Canal is the perfect place to have your morning coffee. Conveniently located near Sandbars, State parks and many attractions.

Superhost

Home in Key Largo

4.91 out of 5 average rating, 100 reviews

New Oceanside Casa Azul! Voted #1! Golf Cart-Beach

No hidden fees! Casa Azul blends luxury and laid-back island vibes in the heart of Key Largo. With Superhost status and hundreds of 5-star reviews, a perfect escape. Voted the #1 Vacation Rental in Key Largo, it’s ideal for families, couples, and groups alike. Enjoy a free golf cart, fast Wi-Fi, 2 pools, private beach, saltwater lagoon, kayaks, tennis and pickleball courts with gear, marina access, boat ramp, trailer parking, and optional slip rentals. Salt Life meets luxury - this is the one.

Guest favourite

Apartment in Key Largo

4.93 out of 5 average rating, 154 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

Guest favourite

Condo in Tavernier

4.99 out of 5 average rating, 106 reviews

Modern and Coastal Ocean Pointe 2307

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy our newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

Guest favourite

Home in Marathon

5 out of 5 average rating, 33 reviews

Waterfront Escape -VACA-23-408

Come stay at this brand new home construction on a deep and wide canal leading to the ocean with pool and exotic decor. 75 foot dock with water and electric. Top of the line appliances with a fully stocked kitchen. Spa style showers with high end decor. Luxury at its best. Heated pool with sundeck and lots of seating around the edges. (Pool heater is an additional $100 per stay). Ground level cooking and dining for those beautiful days after boating or while laying around in the pool.

Superhost

Cottage in Cudjoe Key

4.64 out of 5 average rating, 111 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

Superhost

Townhouse in Key Largo

4.82 out of 5 average rating, 110 reviews

Oceanfront Resort W/Indoor Pickleball - Spacious!

An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. This 3/3.5 villa is located in Key Largo's most upscale oceanfront resort. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simply desire the very best in luxury accommodations.

Superhost

Condo in Tavernier

4.76 out of 5 average rating, 365 reviews

Florida Keys Getaway - Slps 4 - Ocean View

Check out this recently remodeled 1-bedroom condo with relaxing and tasteful beach decor - perfect for your Keys Getaway. Ideally located between Key Largo and Islamorada, it offers the best of both worlds! Ocean Pointe is an oceanfront condo property that's just steps away from all the Keys have to offer - the world's best fishing, diving, snorkeling, paddle boarding, and kayaking.

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What guests are saying

Gone Coastal 2

4.92 out of 5 average rating, 53 reviews2 weeks ago

My family and I loved our trip to Key West. This was our first time booking through Airbnb. We were so happy we went with Chris place. It was clean, spacious and comfortable. We would definitely stay here again. We loved sitting on the balcony and enjoy our morning coffee. It was just so very peaceful. I would highly recommend this property.

Home in Key West

What guests are saying

Catch n' Relax Canalfront Cottage in Marathon

4.97 out of 5 average rating, 32 reviews1 month ago

We stayed for 11 nights at Wendy's beautiful home. We had everything we needed for our entire stay. The area is very quiet and peaceful. It was so lovely walking up on the water and enjoying breakfast outside. Extra touches like having bikes and kayaks to use were also sooo nice! Wendy was very helpful with local spots to check out as well. We will definitely be back!

Cottage in Marathon

What guests are saying

Waterfront Oasis3/2 Direct Ocean

5 out of 5 average rating, 3 reviews9 months ago

Beautiful views and great spaces! We’ve stayed in Marathon several times in different canal houses with our family of 7, and this property is now our new favorite. We couldn’t get enough of all the beautiful views from sunrise to sunset whether it was on the porch, in the pool, or out by the Tiki Hut. Every bedroom has water views as well. Boat access was an easy out to snorkeling, diving, fishing, or whatever you like to do. There are two kayaks for use, which made for some nice outings to explore the immediate area. The kitchen had everything needed for cooking, and even had an extra under-the-counter ice machine. We had a great time here, and would stay again. Thank you to the owners for sharing your property.

Home in Marathon

What guests are saying

146 RV Vacation Rental n Key Largo Kampground, FL

4.92 out of 5 average rating, 26 reviews2 weeks ago

Julie’s place was great as a snowbird escape! The weather in Key Largo is fantastic and her location is great! The pool was heated and had plenty of deck chairs. The sandy beaches at the campground made it super easy to launch our kayaks and get to the mangrove kayak trails super fast. There are so many restaurants in town to try, and Publix grocery store is super close (walkable if needed). Her outside patio is super relaxing and has an outside tv (where we watched the Super Bowl). The bikes at her site were a great amenity too! We loved our time at Julie’s place!!!

Campervan/RV in Key Largo

What guests are saying

Incredible townhouse in Key West

5 out of 5 average rating, 7 reviews33 months ago

We loved our stay in Key West! It’s on the southern end of Duvall Street, but we never had an issue walking to shops or restaurants. The stay was within a resort that is very well kept and quiet. We felt like the inside of the townhome was nicer than the pictures showed. Harry was an excellent communicator and quick to respond to all of our questions. We had a blast!

Home in Key West

What guests are saying

VOTED TRIPADVISOR'S #1 DESTINATION, POOL, TENNIS

4.84 out of 5 average rating, 69 reviews1 month ago

Pedro was extremely helpful and very responsive with communication. We had a few hiccups but Pedro was able to help sort it out. Beautiful house! Beautiful neighborhood! Very relaxing and accommodating for all ages and families! We had our 3 year old and 7 month old with their grandma and we all had a blast. Would definitely return!

Townhouse in Key Largo

What guests are saying

Amazing Bayfront New House with Dock and Pool!

5 out of 5 average rating, 34 reviews1 month ago

We had a great stay. The highlights were the view of the bay and the heated pool. The beds were comfortable and the open space was great to gather as a family. Unfortunately we didn’t catch too many fish but had a great time trying. The paddle boards were perfect for our teenage kids. Would definitely love to return.

Home in Marathon

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