The Best Vacation Rentals to Book in the Florida Keys

Get to know the local flora and fauna while staying in your Florida Keys vacation rental at the Reef at Marathon
Get to know the local flora and fauna while staying in your Florida Keys vacation rental at the Reef at Marathon | Courtesy of the Reef at Marathon by Capital Vacations / Expedia
Photo of Nick Dauk
1 December 2021
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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.

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

Large pool area with palm trees at Angler's 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.

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

Immense zero-entry pool at Mariner's Club Key Largo by KeysCaribbean in the Florida Keys
Courtesy of Mariner's Club Key Largo by KeysCaribbean / Expedia
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.

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

A white heron sits on the dock at the Reef at Marathon by Capital Vacations in the Florida Keys
Courtesy of the Reef at Marathon by Capital Vacations / Expedia
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.

Coconut Mallory Resort And Marina By Kees Vacations, for condo cool in Key West

The marina in front of the Coconut Mallory Resort and Marina by Kees Vacations on Key West
Courtesy of Coconut Mallory Resort and Marina by Kees Vacations / Expedia
Just far enough from the beer-swilling Duval Street yet still on Key West proper, these condos are far from one-size-fits-all. A studio or one-bedroom is plenty for an intoxicating solo trip around the bars of Key West while the spacious two-bedroom condos are good for kicking back with your friends. Smathers Beach is a three-minute drive, though if you’re going to cab it, spend the extra two bucks to hit Higgs Memorial Beach Park – it’s within walking distance of Old Town.

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

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

Anglers Reef Villa 1, for the personal touch on Islamorada

Exterior view of plantation-style Anglers Reef Villa 1 set among row of villas in different colors on Islamorada
Courtesy of Anglers Reef Villa 1 / Expedia
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.
These recommendations were updated on December 1, 2021 to keep your travel plans fresh.

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