Places to stay near Highland Beach

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Top-rated vacation rentals near Highland Beach

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Top guest favorite

A modern bathroom is presented, featuring a standalone tub and a spacious walk-in glass shower. A stylish vanity with storage is complemented by a decorative plant and vibrant floral accents. Light streams in through the frosted window, enhancing the bright, airy atmosphere.

Apartment in Naples

5 out of 5 average rating, 27 reviews

Greenlinks Flamingo Villa-Pool/Golf/Gym/Tennis

One of the best condos at Lely resort Greenlinks! Classic Mediterranean architecture, spacious and beautiful white coastal Florida interior design with modern luxuries. High-end finishes, top of the line appliances, all glass showers, standalone tub and incredible amenities you’ll love! Located on a world class golf course, with a heated pool just steps away. We renovated and staged this condo as our personal vacation home and spared no expense, so we’re excited to share it with our VIP guests.

Guest favorite

Two lounge chairs are set on a stone pathway surrounded by tropical foliage, facing a peaceful lagoon. Kayaks are visible along the water's edge, with lush greenery framing the serene view. The inviting outdoor space offers a tranquil atmosphere for relaxation.

Cottage in Naples

4.95 out of 5 average rating, 143 reviews

Tropical Cottage by the Sea- No Storm Damage

Welcome to your own private waterfront home on private lot close to Naples beaches! This small cottage comes with a big view of a tropical, peaceful lagoon. Fish and kayak right from the back yard! Two Kayaks & bikes provided! Lush, tropical setting and lots of wild life to see too! Relax on the back porch where there's always a breeze! Bike over to the Botanical Gardens or one of the many restaurants close by! Short drive to famous 5th Ave & Naples beaches! Lots of fun things to do close by!

Top guest favorite

Condo in Tavernier

4.96 out of 5 average rating, 186 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Guest favorite

Condo in Tavernier

4.97 out of 5 average rating, 108 reviews

Modern and Coastal 3212 is Across from Pool

Are you looking for a Caribbean Vacation in a tropical resort without leaving the USA? Look no further than our Ocean view 2 bedroom and 2 bath condo at Ocean Pointe Suites! Our property offers: 24 hour front gate security, Heated Junior Olympic Pool with 15 person hot tub, tropical Beach, Marina, Tennis/Pickle ball courts. Enjoy the newly re opened ISLAND GRILL pool bar! We are located 60 miles from Miami International Airport and 90 miles from Fort Lauderdale International Airport.

Guest favorite

Home in Marco Island

4.93 out of 5 average rating, 29 reviews

STUNNING Canal Ranch Walk to the Tigertail Beach

NEW LISTING! Newly Remodeled 4 Bed, 2 Bath that sits in a very exclusive location less than 2 blocks from Tigertail Beach! Our vacation home offers an abundance of updated space! Plenty of outdoor entertaining within the large enclosed pool area. Enjoy the several "extras" to use during your stay including, bikes, beach chairs, coolers, and much more! You won't find a better value for your family and be able to walk to the beach! Please note: TV in every room set up for streaming ONLY

Guest favorite

A sandy beach area features multiple blue lounge chairs arranged under coconut trees, all facing the ocean. The clear water reflects the blue sky, and lush greenery outlines the beach, creating a serene coastal environment.

Condo in Tavernier

4.94 out of 5 average rating, 18 reviews

Resort Condo: Pool | Beach | Marina | Pickleball

NEW LISTING! Experience the best of the Florida Keys in this prime location, offering both the luxurious amenities of a high-end resort and the cozy comforts of home, all with stunning views of the turquoise ocean. Enjoy access to an Olympic-size pool, hot tub, beautiful beach, marina, outdoor grills, tennis courts, pickleball, playground, and more. All of this comes at an excellent value, allowing you to spend more on the unforgettable experiences the Keys have to offer.

Guest favorite

A screened-in pool area features a spacious, clear swimming pool surrounded by a light-colored deck. The blue walls of the adjoining room provide a relaxed atmosphere, while large windows allow natural light to enhance the space.

Home in Marco Island

4.96 out of 5 average rating, 27 reviews

2nd Closest House to South Beach Entrance w/ Pool

This perfect family vacation home is the SECOND closest house to the South Beach Entrance- in just mere 4 minutes you will be walking on a white sandy beaches and swimming in the warm waters of the Gulf of Mexico The house offers 3 bedrooms- two with King Size and one with two twin size beds. Pets are considered with additional fee only if approved by owner prior to stay. Think of everything you could possibly want in your dream vacation home and you’ll find it here.

Guest favorite

Townhouse in Naples

4.93 out of 5 average rating, 44 reviews

Pickleball/beach getaway

Located across the street from the Naples Botanical Gardens and less than a mile from East Naples Community Park, come and explore the beauty of Naples from this centrally located home. In less than a 10-minute drive, you can enjoy the pristine white sandy beaches and Naples Pier. The famous 5th Avenue, Historic 3rd Street South, Celebration Park (waterfront bar and food Truck Park), and Three60 Market are all close by. Marco Island is a short 25-minute drive away.

Guest favorite

Two white adirondack chairs are positioned on a grassy area, facing the calm waters of Goodland Bay. A tranquil sunset casts soft hues across the sky, reflecting on the water and enhancing the serene view. Lush greenery outlines the shoreline.

Cottage in Goodland

4.97 out of 5 average rating, 106 reviews

Waterfront View Cottage

Come and stay at the only location on the island with the one of a kind exceptional view of the Everglades. Step right out to the waters edge of the Goodland Bay, where you will be able watch the dolphins right from your porch and private patio. The cottage has great sliding glass doors that hold the magnificent view of the water, right from the living room. A freshly remodeled fully furnished, up to date, 1 bedroom cottage. Dockage, kayaks, and bikes available.

Top guest favorite

Condo in Naples

4.95 out of 5 average rating, 105 reviews

Cool Condo for your Cozy Stay

Perfect vacation! This 2 BD, 2 BTH condo is conveniently located to all Lely resort amenities: gorgeous pool, clubhouse with a great equipment for workout, 4 Star Rated Flamingo and Mustang golf Courses, tennis courts and Sam and Snead's Bar & Grill overlooking the course. Free rounds are available from May to Oct. location is perfect-close to stores, restaurants, and a short drive to beaches (Marco or Naples) & Naples downtown. Enjoy! License # DWE2103418

Top guest favorite

A screened lanai showcases a heated pool with clear blue water, accompanied by a lounge chair. The view extends to a serene canal lined with palm trees and homes, providing a peaceful waterfront atmosphere.

Home in Marco Island

4.98 out of 5 average rating, 302 reviews

⭐ Rare Waterfront Western Exposure Vacation Home

This dream getaway home is located in the heart of Marco Island with everything you need for an unforgettable trip! Enjoy the convenience of being only minutes away from South Marco Beach, with its white sand and clear blue skies, and the best restaurants such as Da Vinci's, Marco Prime, The Snook Inn, The Oyster Bar and shopping on the Island! Wind down your day watching breathtaking Western exposure sunsets from your own waterfront patio and dock...

Guest favorite

A spacious living area features a comfortable sectional sofa adorned with decorative pillows. A stylish coffee table sits at the center, complemented by a simple plant. A large television is positioned on a modern console against a backdrop of clean, white walls and a soft area rug.

Home in Naples

4.95 out of 5 average rating, 201 reviews

Location! Quality! Comfort! " The downtown Gem "

This Completely renovated gem offers a pleasant and cozy open floor plan with high-end beds and furniture, a private patio with a BBQ station, Screened lanai, and it's fully equipped with anything that you can think of. Within half a mile, you will be in the most fun Celebration Park or have breakfast on the water, Naples Botanical Gardens, and much more. You'll also appreciate the short drive to downtown Naples and the best Naples beach.