Holiday rentals 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/Motorhome in Key Largo

4.78 out of 5 average rating, 18 reviews

Casa rodante en el paraíso

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/Motorhome in Key Largo

4.96 out of 5 average rating, 114 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, 101 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

Flat 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

Apartment 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

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

Apartment 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.

Guest favourite

Townhouse in Key West

5 out of 5 average rating, 8 reviews

Exceptional Water View With Boat Dock!

This is the best kept secret. 10 miles from Duval St. for the night life, but a total private oasis if you are looking for a true get away. This is an end unit with a water view from every window in a gated community with a salt water pool. Wake up to an ocean view and have cocktails on the patio. This is a brand unit that has recently been completely renovated.