The Best Vacation Rentals to Book in the Florida Keys

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.

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.

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.

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.

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.

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.