15 Florida Keys Getaways Worth Booking This Year

Across the Florida Keys, certain stays do more than check boxes—they create lasting memories. Some lean into serenity, others into scene-stealing charm. Scroll through and let the one that speaks to you take the lead on your next coastal escape.

Cheeca Lodge & Spa

Set on 27 acres in Islamorada, this long-loved resort blends luxury with a sense of play. Soaking tubs, a 525-foot pier, and a 9-hole golf course create room for indulgence, while the chance of spotting a celebrity or landing a prize fish keeps things interesting.

The Moorings Village

What was once a coconut plantation now feels like a secret sanctuary in the heart of Islamorada. Private villas sit among palms on 18 lush acres, with paddleboards ready by the sand. Scenes from “Bloodline” were filmed here, but the vibe stays quiet and personal.

Tranquility Bay Beachfront Resort

Set in Marathon with its own stretch of sand, this coastal retreat leans into homey comfort. Two- and three-bedroom beach houses include full kitchens, making it easy to settle in. One of the largest pools in the Keys waits just steps away, along with island-inspired dining.

The Perry Hotel & Marina

Stock Island sets the stage for a nautical-chic hideaway with direct access to the marina just steps from your room. Spacious rooms keep things stylish and dog-friendly. With two pools, live music nights, and a changing lineup of food trucks, the vibe stays easygoing and fresh.

Pier House Resort & Spa

This storied Key West resort blends history with indulgence, located just off Duval Street behind a calm, private beach. Once a creative haven for ’60s writers and artists, it now draws adults with its award-winning spa and a discreet clothing-optional sun deck.

Bungalows Key Largo

Designed for adults craving privacy and ease, this all-inclusive getaway in Key Largo surrounds each waterfront bungalow with its own veranda and open-air soaking tub. Dining and water activities are all part of the experience, with spa sanctuaries hidden inside a peaceful Zen Garden.

Casa Morada

This boutique hotel in Islamorada keeps things intimate with just 16 suites and a calm, coastal atmosphere. A narrow footbridge leads to a private island escape, while the saltwater pool and garden yoga add to the peaceful rhythm. Its boho spirit even welcomes pets.

Ocean Key Resort & Spa

At Zero Duval Street in Key West, the resort sits just steps away from Mallory Square. Every room includes a private balcony overlooking the Gulf. At SpaTerre, tropical-inspired treatments await. And, across the property, Hot Tin Roof treats guests to breathtaking sunset meals.

Playa Largo Resort & Spa

A 14.5-acre expanse in Key Largo delivers coastal comfort with a range of beach houses, breezy bungalows, and hotel rooms. Paddleboard yoga delivers calm on the water. As the sun sets, beach bonfires spark unforgettable moments. Recognition from “Travel + Leisure” speaks for itself.

Sunset Key Cottages

Just 500 yards off Key West, a private ferry carries you to a 27-acre island that feels like another world entirely. Cottages come with wraparound porches and full kitchens, while breakfast arrives in a wicker basket at your door each morning like a quiet ritual.

Little Palm Island Resort & Spa

Reachable only by boat or seaplane, this adults-only island retreat offers oceanfront bungalows with outdoor showers. There are no TVs or phones in the rooms, making it perfect for a digital detox. Torch-lit dinners and key deer sightings add to its rustic charm.

Lime Tree Bay Resort

A quiet half-mile beach in Long Key stretches out in front of a laid-back resort that embraces simplicity and space. Oceanfront hammocks sway in the breeze, as kayaks and bikes sit ready at no extra cost. It’s a simple kind of charm that feels rare.

The Gardens Hotel

Hidden within Old Town Key West, this adults-only retreat feels like a step into another era. Once a private estate in the 1800s, it now wraps its guests in tropical gardens, gurgling fountains, and the kind of nights where jazz and wine linger side by side.

Isla Bella Beach Resort

Located in Marathon with over a mile of private shoreline, the oceanfront resort has five pools and a marina with jet skis. It’s suited for both romantic getaways and family trips. The Gulf sunsets alone make it worth the stay.

La Te Da Hotel

Deep roots in Key West’s LGBTQ+ community give this boutique inn a sense of history and heart along Duval Street. Rooms open to the pool and the rhythm of live cabaret shows. It’s all set against a backdrop of colonial charm and bold tropical flair.