The Best Vacation Rentals To Book In The Florida Keys

Nearly 2,000 islands form the Florida Keys, but you’ll only need to visit one to fall into step with the laid-back lifestyle. From Key Largo down to Key West, the Overseas Highway will cruise you through some of the best fish shacks, beaches and sunsets in the state. Family fun and solo shenanigans await on each key, as do self-catering rentals that feel just like home. Opt for one of these top vacation rentals in the Florida Keys, bookable on Culture Trip.

1. Angler's Reef Resort by KeysCaribbean, for your own oasis on Islamorada

Resort, Villa

Large pool area with palm trees at Anglers Reef Resort by KeysCaribbean on Islamorada

Blue skies, green lawns, clear waters and a townhome that’ll feel like your home within minutes – Angler’s Reef Resort on Islamorada seems too good to be true. A private beach is yours to dig into if you can’t find the perfect spot to tan by the pool. Spacious floor plans with enough room for six won’t make any one in your group feel cramped. If someone does get a little cabin fever, they’re only steps away from the marina where a boat can take them into miles and miles of nothing but fresh air and soft waves.

2. Mariner's Club Key Largo by KeysCaribbean, for Miami moments in Key Largo

Resort, Villa

Immense zero-entry pool at Mariners Club Key Largo by KeysCaribbean in the Florida Keys

Who said the best vacation rentals in the Florida Keys were down south? Key Largo is home to the Mariner’s Club, an easy-breezy vacation destination with suites, villas and townhomes. You don’t need to truck it to Key West for good vibes; spend more time in the sun splashing in two outdoor pools or watching the boats float in the marina. Only 90 minutes from downtown Miami, it’s a prime South Florida vacation that offers the best of both worlds.

3. The Reef at Marathon by Capital Vacations, for plain sailing in Key West

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A white heron sits on the dock at the Reef at Marathon by Capital Vacations in the Florida Keys

A helpful tip to securing the best vacation rentals in the Florida Keys: consider the water your roadway. The Reef at Marathon has its own marina, allowing you to trade the drive to Key West for a relaxing sail. You may not leave this condo willingly, though; it’s a two-bed, two-bath with an ocean view, full kitchen and outdoor tennis courts by the pool for outdoor playtime. If you need to bail for a bit, take a complimentary bicycle for a spin.

5. Topsider Resort by Capital Vacations, for making a splash on Islamorada

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View from the end of the long narrow pier toward the beach and condos at Topsider Resort by Capital Vacations on Islamorada

Get to know the bayside of Islamorada at Topsider Resort. This two-bedroom, two-bathroom private condo two minutes from Anne’s Beach is picture-perfect for two couples. No need to unpack all of your clothing – a private beach, an outdoor pool and four hot tubs will keep your crew in your bathing suits the entire trip. If you’re keen to both feed tarpon and feed on tarpon, Robbie’s will be your Overseas Highway haunt.

6. Anglers Reef Villa 1, for the personal touch on Islamorada

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A private waterfront villa with its own outdoor pool, you’ll spend your days either relaxing on the private beach or taking a free bicycle around the island of Islamorada. The full kitchen, hydromassage showerhead and Egyptian cotton sheets add a touch of resort luxury to the home-like comfort. This villa also has a second bedroom, in case you want to share the water views from one of the best vacation rentals in the Florida Keys with a few very special friends.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

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