Best Places to Stay in Middle Keys

Nestled amid the Gulf of Mexico and the Atlantic Ocean, the Middle Keys is home to spectacular white sandy beaches like Sombrero Beach and Coco Plum Beach.

State parks like the Curry Hammock State Park and Long Key State Park not only have wonderful beaches but also feature nature trails, picnic areas, beachside RV and tent camping, and more.

This part of Florida is truly a paradise where one can lounge on the beach, swim, snorkel, hike, fish, and marvel at native and tropical wildlife.

Planning your next vacation in Florida? You’re in luck! Here’s your guide to the best places to stay in Middle Keys. Let’s dive in.

Beachfront resorts that are best places to stay in middle keys

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Tranquil Beachfront Resorts

This tropical paradise is the perfect place to escape the daily grind and indulge in luxury and tranquility. Staying at a beachfront resort in the Middle Keys allows you to enjoy the breathtaking views.

Imagine waking up to the sound of waves crashing against the shore. And, as you step outside, you are greeted by the panoramic vista of crystal clear waters and swaying palm trees.

Beach resorts that are the best places to stay in middle keys

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Casa Marina Resort

The Casa Marina Resort, located on the southernmost tip of the island, is an iconic resort that boasts stunning ocean views and a private beach on the Atlantic Ocean.

It is one of the top beachfront resorts in Key West, featuring elegant rooms, tropical gardens, and two oceanfront pools.

The Reach by Hilton in Key West

The Reach Key West is a slice of paradise that offers the ultimate intimate and secluded experience.

This resort is located on a private beach, with spacious rooms, a spa, an infinity pool, and a beachfront restaurant.

white sand and clear blue water are best places to stay in middle keys

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Playa Largo Resort and Spa

The Playa Largo Resort and Spa is a luxurious resort situated on 14 acres of natural beachfront overlooking the Atlantic and a tropical pristine white sand beach.

This tropical oasis in the heart of Key Largo, Florida, offers spacious rooms, a private beach, and a full-service spa. Indulge in a spa treatment or spend the afternoon on a private floating water cabana.

Bungalows Key Largo

Experience Key Largo’s relaxed cabana lifestyle at the Bungalows Key Largo. This adults-only, all-inclusive resort offers a unique and unforgettable beachfront stay.

This have features spacious bungalows with private outdoor soaking tubs, luxurious private verandas, a private beach, an infinity pool, and several dining options.

Ocean Pointe Suites of Key Largo

Ocean Pointe Suites of Key Largo is a secluded, waterfront resort located on a 60-acre private reserve overlooking the Atlantic Ocean.

This oceanfront sanctuary offers a private sandy beach, Junior Olympic pool, deep-water marina, panoramic oceanfront gazebo, two tennis courts, two bars, and a waterfront café.

A poolside with pine trees are the best places to stay in middle keys

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Cozy Island Villas

Villas offer a more intimate setting during your stay in the Middle Keys. Below are some of the best villas that provide all the amenities to make your vacation comfortable and luxurious.

Key West Villas

Key West Villas allows you to experience this unforgettable island to the fullest. Conveniently located just 200 feet from the world-famous Duval Street, you can walk to some of the best restaurants and attractions in the historic Key West area.

Choose from their selection of well-appointed accommodations – stand-alone villa, bed and breakfast style guest room, or suite – and enjoy the relaxation and comfort with all the amenities of home.

Girl enjoying the sunset by the pool on the best places to stay in middle keys

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Leaward Isle Island Retreat

Leaward Isle Island Retreat Villa offers amenities like a tennis court, a sauna, and a golf course to add fun and relaxation to your stay. It is located near several attractions as well, making it easier to make the most of your vacation.

The Key West Nature Preserve, Nancy Forrester’s Secret Garden, Smathers Beach, and Higgs Beach Dog Park are just a few of the places you can conveniently access from your villa.

“Keys, Please” by Brightwild

“Keys, Please” offers the perfect private getaway with a picket fence that leads to your own resort-like oasis. The home features a private pool perfect for relaxation or entertaining year-round.

This vacation home is just a few minutes away from the world-famous Southernmost Point, Duval Street, South Beach, Higgs Beach, Fort Zachary Taylor State Park Beach, Ernest Hemingway Home and Museum, and historic points of Key West.

Woman by the pool on the best places to stay in middle keys

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Pilar Cottage by Brightwild

Pilar Cottage is part of the quiet complex called “Harborwalk Hideaways,” located right in the heart of the Historic Seaport District.

This villa features a small, shared dipping pool with a waterfall feature, a patio, and a spacious outdoor area. Nearby attractions include Key West Aquarium, Simonton Street Beach, Duval Street, South Beach, and Fort Zachary Taylor State Park Beach.

Somewhere on the Beach

Somewhere on the Beach boasts amazing views of the Atlantic Ocean and White Street Pier. You can watch the sunset over the Atlantic from your living room or from the comfort of your bedroom.

The villa features a large private balcony, three lighted tennis courts, a clay court, an exercise room, and a library.

Wrap Up

The next time you visit the stunning beaches of Middle Keys, here’s your shortlist of the best places to stay in Middle Keys for the ultimate relaxation and comfort.

And if you’d like to stay here for good, let’s talk! I can show you all the best homes in Middle Keys. Don’t hesitate to give me a call or send me an email so we can schedule an appointment.

You may contact me at 305-912-2177 or send me an email at

Frequently Asked Questions

The best months to visit Middle Keys is during the dry season, between November and April.

Yes, some of them are Sunset Cove Beach Resort, Deckhouse, Rose Lane Villas, and Old Town Manor.

If you plan to stay anywhere in the Florida Keys, you will need to rent a car. Almost everything is close to the highway, and it is extremely busy. Taxis and shuttles are also available for short- and long-distance travel.