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Places to stay near Highland Beach

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Top-rated vacation rentals near Highland Beach

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Top guest favorite

The open living and dining space is illuminated by natural light, featuring a neutral palette and modern furnishings. Floor-to-ceiling windows provide unobstructed views of the ocean, while a cozy seating area and a dining table invite relaxation and enjoyment of the surroundings.

Condo in Marco Island

5 out of 5 average rating, 14 reviews

August Special: Beachfront unit w/amazing views

Enjoy the stunning ocean views from every room, watch the colorful sunsets from the comfort of this home! Feel at home as this condo is truly set up to provide you with everything you need during your stay – kitchen, bedroom and bathroom essentials, beach gear, you name it! Access to Crescent beach and Tigertail beach, outdoor heated pool, fitness center in the building, outdoor tennis and pickleball courts; best restaurants and boutique shops within walking distance or just a short ride away.

A wooden dock juts out over calm water, flanked by mangrove vegetation. Two adirondack chairs are positioned for relaxation, offering unobstructed views of the water. A cozy cottage is visible in the background, surrounded by palm trees, under a clear blue sky.

Cottage in Everglades City

4.98 out of 5 average rating, 160 reviews

The Cypress Cottage!

Welcome to the Cypress Cottage! A home designed with sportsmen & nature enthusiast in mind. Whether you are exploring inland in Big Cypress or Navigating through the Everglades & Ten-Thousand Islands you'll have a comfortable place to re-charge with panoramic views of mangrove jungle. Cypress Cottage offers parking for (4) vehicles with room left over for your boat or kayak trailer. Our dock offers the perfect place to keep your boat so you can make the most of your Everglades Adventure.

A charming blue cottage with an inviting entrance is surrounded by lush tropical vegetation. The exterior features a garage and large windows that enhance the cottage's character. Palm trees gently sway in the breeze, adding to the relaxed island atmosphere.

Home in Marco Island

4.97 out of 5 average rating, 115 reviews

Boater’s Paradise at the Coastal Cottage!

Perfect ENTIRE HOME for a seaside retreat! Direct access 3/2 with boat lift and dock. Charmingly furnished and designed to delight. Enjoy amazing access to Florida's best boating, fishing and beaches- just 4 minutes from the dock to end of no wake zone and a 12 minute car drive to stunning local beaches. Enjoy upstairs screened lanai overlooking tranquil waters and feel your troubles melt away as you relax in the tranquil island vibe of Old Florida! Boat rental available at near by marina.

Top guest favorite

A bright living area is furnished with comfortable sofas and a coffee table. Light blue walls enhance the spaciousness, while a ceiling fan circulates air. A large television is mounted on the wall, and glass doors offer a view of the outdoor pool area.

Home in Marco Island

4.97 out of 5 average rating, 149 reviews

Beachy Chic house Free bikes/SUPs Less mile beach

Beautifully renovated beach house walking or short bike ride to everything you need to enjoy Marco Island's beautiful weather. New, designer furnishings decorated in beachy chic. 3 bed, 2.5 bath. Great location 7/10 mile from Tigertail beach. 3 min bike ride or short walk to beach. Beautiful large pool and screened lanai for al fresco dining. Walking to many restaurants. Everything you need for fun at in the sun: Bikes, umbrella, cooler, beach towels. Enjoy paradise at your own pool home!

The exterior of a remodeled beach house is displayed, featuring a landscaped yard with palm trees and a swimming pool. A dock is visible on the canal, accommodating a boat and paddleboards. Large windows reflect the openness of the home, inviting natural light.

Home in Marco Island

4.89 out of 5 average rating, 117 reviews

Family Tigertail Beach Home -Completely Remodeled!

Our Tigertail Beach house has been completely remodeled. Completely remodeled inside and out to mid-modern beach décor. Located in a very quiet and private neighborhood yet only a short walk to Tigertail Beach. Close to several restaurants, grocery stores, shopping, and much more! The house offers 4 bedrooms and 3 full bathrooms. 3 King Beds, 1 Queen Sofa-Sleeper, 2 Twin Bunk Beds, and a Pack n' Play if needed. Perfect house for your family beach getaway! Our reviews speak for themselves!

A vibrant blue island home with a welcoming front entrance, surrounded by manicured green grass. Lush tropical plants and flowering shrubs enhance the landscape. A paved driveway leads to a single-car garage, under a light-colored roof, set against a bright sky.

4.97 out of 5 average rating, 249 reviews

Island lifestyle family vacation home (Salt Pool)

A stylish, brand new island home perfect for vacationing with your own private heated pool. The West Hilo Home sleeps 8 and is within 3 blocks of local restaurants that feature dining on the water in sunny Isles of Capri. Enjoy laid back island life- including kayaking, boating, fishing and jet skiing just minutes away. Neighboring Marco Island is less than 10 minutes by car and famous for their powder white sand beaches. Or relax at home grilling by the pool while the sun sets.

A new construction home is showcased, featuring an elegant entrance with arched doorways and a prominent front porch. Lush green grass surrounds the property, complemented by tropical palm trees. Bright blue skies add to the inviting atmosphere of the exterior.

Home in Marco Island

4.97 out of 5 average rating, 155 reviews

Lux Comfortable Home Sun On The Lanai All Day

Welcome to your perfect island getaway! This stunning 4-bedroom, 3-bath custom home is impeccably maintained, spotlessly clean, and beautifully furnished for ultimate comfort. Enjoy spacious living areas, a well-stocked kitchen, and two king suites with en suite baths. Open the glass wall to lounge outdoors, dine al fresco, or soak up the sun on the cantilever canal dock. Relax by the heated pool under the lanai and take in serene waterfront views—your dream escape awaits!

An open-concept living area features a comfortable sofa and a cozy chair, oriented towards a 55" HDTV mounted on the wall. A dining table with seating for four is nearby. Natural light streams in from large windows, enhancing the welcoming atmosphere.

Apartment in Marco Island

4.94 out of 5 average rating, 265 reviews

Best JW Marriott Alternative Prime~ Location~Pool

Retreat to the gorgeous 1BR 1Bath coastal oasis located across the street from JW Marriot, offering easy access just steps to the amazing beach on Marco Island. The condo's comforts, amenities, and wonderful location provide everything you need to relax, recharge, and have a perfect Gulf Coast stay! ✔ Large 1bd w King Bedroom ✔ Open Design Living ✔ Full Kitchen ✔ Balcony ✔ Smart TV ✔ High-Speed Wi-Fi ✔ Community Amenities (Pool, Hot Tub, Free Designated Parking)

Top guest favorite

The exterior of the cottage features a welcoming entrance flanked by two comfortable chairs on a brick paved patio. Lush greenery and palm trees surround the space, creating a serene atmosphere. Large glass doors lead into the interior, inviting natural light.

Cottage in Goodland

4.98 out of 5 average rating, 121 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.

The illuminated pool glistens in a tranquil setting, adorned with floating yellow lily candles. Lounge chairs with striped towels are positioned beside the water, while soft lights provide ambiance around the area, creating a serene space for relaxation.

Home in Marco Island

4.97 out of 5 average rating, 138 reviews

Top-rated luxury pool home in prime location

🏠Newly renovated & professionally designed 👙Amazing pool and outdoor kitchen (including grill, pizza oven, fridge)! 🏖️4 mins to beach 🌊Beach chairs, umbrellas, beach wagon & bikes 🐶Low pet fee; we love our 4-legged guests! 🧻Household supplies and personal amenities included ✅Fully stocked chef’s kitchen 🛌🏽Super comfortable beds for ultimate comfort and sleep 💻 High speed internet with dedicated workspace 😊24/7 local & professional host support!

Top guest favorite

A child stands on a sandy beach, holding a large shell with both hands. The clear blue sky and soft clouds create a bright backdrop, while the expansive shoreline leads to a tranquil ocean in the distance.

Condo in Marco Island

4.9 out of 5 average rating, 222 reviews

By the Ocean

This building is located right in front the Marco Island Beach Access Point! This condo is very close to the JW Marriot, providing a convenient alternative. The condo has a pool - available all year -, tennis court, BBQ and laundry on each floor. All the common areas are fully available for your use and in excellent condition. And of course, you have a reserved parking space for your vehicle. This is an exceptional place to rest and enjoy with your family.

Top guest favorite

A spacious living area is filled with natural light, featuring a comfortable sectional sofa and armchair arranged around a coffee table. A flat-screen TV is mounted on the wall, with access to the open kitchen visible through an adjoining doorway.

Condo in Marco Island

4.93 out of 5 average rating, 206 reviews

Marco Island Beach Club 201 - Modern 2 bed/ 2 bath

Enjoy the comfort of this bright, clean 2nd-floor, end-unit condo at Marco Island's Beach Club. Save money compared to expensive hotels and enjoy all the amenities of home. With 1,100 sq ft, this condo is ideal for a couples getaway or family vacation. Located on the peaceful south end of Marco Island, the Beach Club is just a short walk from over six bars, restaurants, a movie theater, and mini-golf—only three blocks away. The Marriott is just a mile away.

Popular amenities for vacation rentals near Highland Beach

Free parking on premises

Air conditioning

Condo rentals with wifi

Aerial view showcases a beachfront condo complex with multiple buildings surrounded by palm trees. The sandy beach and ocean are visible in the background, with lounge chairs arranged along the shore. A heated pool and landscaped areas can be seen within the property, contributing to a serene coastal setting.

Condo in Marco Island

4.94 out of 5 average rating, 166 reviews

Marco Beach Ocean Resort 707

Top guest favorite

A bright dining area is set up with a large table adorned with plates, glasses, and a basket of flowers. Large windows provide a stunning view of the ocean and sky, enhancing the inviting ambiance of the space.

Condo in Marco Island

5 out of 5 average rating, 19 reviews

Luxe Beachfront, Front Corner Balcony, BIG VIEWS!

Top guest favorite

A view from the property showcases a tree-lined road that leads towards the beach, with glimpses of the Gulf of Mexico visible in the distance. Lush palm trees frame the scene, highlighting the surrounding residential buildings.

Condo in Marco Island

4.98 out of 5 average rating, 111 reviews

Renovated - Minutes to beach access.

A vibrant sunset casts warm hues across the sky and reflects on the calm water below. The shoreline is bordered by lush greenery, while a winding sandy path leads towards the beach, enhancing the scenic view of the surrounding landscape.

Condo in Marco Island

4.94 out of 5 average rating, 127 reviews

Beachfront condo,stunning views,wraparound balcony

A spacious building with a modern design is flanked by palm trees under a clear blue sky. The entrance is marked by a covered area, with a parking lot visible in the foreground, offering ample space for vehicles.

Condo in Everglades City

4.8 out of 5 average rating, 192 reviews

Everglade Isle Palms Condotel w/ Pool & Boat Ramp

Top guest favorite

The sunset casts a golden hue over the calm waters of the Marco River. Silhouettes of palm trees and docked boats frame the view, while the sky transitions through warm shades of orange and blue. Reflection of the sun dances on the water's surface.

Condo in Marco Island

4.95 out of 5 average rating, 110 reviews

Breezy Island Paradise on Marco River

Top guest favorite

A tranquil pool area is showcased, surrounded by lounge chairs and palm trees. The inviting water reflects the blue sky and waterfront views of lush greenery. The building nearby features a light exterior, complementing the serene atmosphere of the space.

Condo in Marco Island

4.99 out of 5 average rating, 125 reviews

Waterfront View, Boat Dock, Pool Wildlife &Fishing

A modern living area features a spacious gray sectional sofa adorned with decorative pillows. A low black media unit houses a flat-screen television. Natural light flows through large sliding glass doors, leading to a balcony with seating, adorned with vibrant green foliage outside.

Condo in Marco Island

4.96 out of 5 average rating, 193 reviews

Newly renovated and beautiful condominium

Family-friendly house rentals

Top guest favorite

A single-story home is framed by lush greenery and colorful landscaping. A welcoming entryway is visible, featuring arched windows and a shaded porch. The driveway leads to a garage, with palm trees swaying gently in the breeze under a clear blue sky.

Home in Marco Island

5 out of 5 average rating, 37 reviews

NEW Island Paradise With Private Heated Pool/Dock

A serene dock extends into the water, featuring two lounge chairs with green cushions. Lush palm trees and landscaped homes are visible across the canal, under a partly cloudy sky.

Home in Marco Island

4.91 out of 5 average rating, 156 reviews

Casa De Mar- Escape to Paradise!

A waterfront home is displayed, framed by lush palm trees and vibrant greenery. A spacious boat dock extends into the calm water, accommodating several boats. The house is adorned with a screened patio, visible from the canal, reflecting a serene outdoor living environment.

Home in Marco Island

4.97 out of 5 average rating, 36 reviews

Waterfront Marco Island w/ Direct Gulf Access!

Top guest favorite

A private swimming pool is encased within a screened-in enclosure, offering protection from insects. Sunlight reflects off the water, creating a shimmering effect. Lounge chairs are positioned nearby, complemented by a grassy area lined with lush greenery.

Home in Marco Island

4.96 out of 5 average rating, 51 reviews

Echo Beach Oasis

A single-story home is set against a bright sky, featuring a spacious lawn framed by neatly trimmed bushes. Palm trees accentuate the entrance, and a screened porch is visible, showcasing the home’s inviting exterior. The driveway is paved, leading towards the entrance.

Home in Marco Island

4.82 out of 5 average rating, 117 reviews

Your Island Paradise Awaits!!

Top guest favorite

A modern single-story home is showcased with a sleek facade and an inviting entryway. A well-maintained driveway leads to a garage, with green landscaping and carefully arranged plants adorning the front. Large windows allow natural light to fill the interior space.

Home in Marco Island

4.98 out of 5 average rating, 91 reviews

Flamingo Paradise 4 min walk from Beach Access.

Top guest favorite

A spacious outdoor area features a glowing salt-water pool under soft, blue lighting. Surrounding the pool, lounge chairs and a hot tub are positioned on a stone patio, all beneath a canopy with ambient string lights that enhance a calming evening atmosphere.

Home in Marco Island

5 out of 5 average rating, 24 reviews

7 Min Beach/Pool/Heater/Game Room/EV chaeger

Top guest favorite

A spacious outdoor area showcases a swimming pool and a hot tub, surrounded by a screened enclosure. Comfortable seating is arranged nearby, with a dining table set under an umbrella. Bright green murals add a touch of color to the white walls.

Home in Marco Island

4.97 out of 5 average rating, 30 reviews

Sunset Serenity | Heated Pool | SPA |5min Beach

Apartment rentals with air conditioning

A swimming pool is shown with clear water reflecting the sun. Palm trees are positioned nearby, silhouetted against a bright sky. The pool area overlooks a tranquil bay, with gentle waves visible in the distance, enhancing the serene outdoor setting.

Apartment in Marco Island

5 out of 5 average rating, 7 reviews

Marco Island Patio Home/Condo direct Bay location

Top guest favorite

A marina is depicted with multiple boats moored along a calm waterway. Clear blue skies reflect on the water's surface, while palm trees line the background, adding greenery to the scene. The image conveys a sense of tranquility and leisure.

Apartment in Naples

4.96 out of 5 average rating, 27 reviews

Serenity Studio: Waterfront & Wildlife Everglades

A private balcony is showcased with a wooden table and two woven chairs, providing a view of palm trees and sunset colors in the sky. A ceiling fan is mounted above, and a decorative rug adds warmth to the space.

Apartment in Marco Island

4.95 out of 5 average rating, 37 reviews

Best Waterfront Retreat 406

A bright dining area features a wooden table with six chairs, accompanied by a decorative centerpiece. Large windows allow natural light and showcase ocean views. The adjoining living space includes a comfortable sofa, a ceiling fan, and a television mounted on the wall.

Apartment in Marco Island

5 out of 5 average rating, 5 reviews

New listing, gorgeous unit!

Top guest favorite

A view of the calm canal is framed by lush green foliage and sturdy tree branches. The still waters reflect vibrant blue skies and elements of nature. Small kayakers are seen paddling, highlighting the tranquil setting amidst the serene environment.

Apartment in Marco Island

4.97 out of 5 average rating, 38 reviews

Marco Island Palm House (1 bedroom with loft)

The inviting living area features two vibrant orange chairs and two teal tables. A spacious grey sofa offers additional seating. A large television displays a beach scene, and colorful artwork adorns the walls, contributing to a light and lively atmosphere.

Apartment in Marco Island

5 out of 5 average rating, 9 reviews

Modern JW Marriott Alternative - Beach Access

A spacious living area features a light-colored sofa paired with two accent chairs, creating a comfortable seating arrangement. A round dining table, set for four, stands adjacent to the entrance to a balcony. Natural light filters through large glass doors, enhancing the serene atmosphere.

Apartment in Marco Island

4.93 out of 5 average rating, 41 reviews

Condo in Marco Island!

A spacious living area features large windows offering views of the outdoors. Two light-colored sofas are adorned with turquoise and blue accent pillows. A striped armchair complements a coffee table arranged on a patterned rug, while decorative art is displayed on the walls.

Apartment in Marco Island

4.96 out of 5 average rating, 23 reviews

Gorgeous Beachfront View Condo in Marco Island

Other great vacation rentals near Highland Beach

An inviting outdoor space showcases a curvy swimming pool surrounded by several sun loungers. Lush palm trees provide shade, while views of the canal and dock area are visible in the background, creating a serene waterfront atmosphere.

Home in Marco Island

5 out of 5 average rating, 19 reviews

Total Haven on Marco Island

Top guest favorite

A welcoming entrance to the home features a spacious front porch with double doors framed by large, arched windows. Lush landscaping includes various plants and stones, creating a well-defined pathway leading to the entrance. The architecture incorporates a tile roof and a modern design.

Home in Marco Island

4.98 out of 5 average rating, 58 reviews

Gorgeous Marco Island Pool Home near Mackle Park!

An outdoor living space is highlighted by a large dining table surrounded by eight chairs. A lounge area is positioned adjacent, featuring a sectional sofa and coffee table. The background features a scenic canal and visible palm trees, with a heated pool adding to the inviting atmosphere.

Home in Marco Island

5 out of 5 average rating, 4 reviews

New Construction - Wide Water View with Pool, Spa

Top guest favorite

A spacious screened-in pool area features a large, shimmering pool alongside a built-in spa, surrounded by a tiled deck. Lounge chairs are positioned nearby, offering a perfect spot for relaxation. Lush greenery lines the perimeter, enhancing the tranquil outdoor setting.

Home in Marco Island

4.97 out of 5 average rating, 35 reviews

Elegant 4BR Marco Home l Pool l Hot tub

Top guest favorite

A stilt home is surrounded by lush greenery, featuring palm trees and manicured grass. The entrance is accessible via a white staircase leading up to a screened porch, emphasizing the elevated structure among the tropical landscape.

Home in Chokoloskee

5 out of 5 average rating, 80 reviews

The Reel'em Inn, Chokoloskee Island Paradise

A spacious balcony offers panoramic gulf views, featuring a glass dining table surrounded by six chairs. The railing provides an unobstructed sightline to the shoreline and blue water beyond, with clouds softly adorning the sky.

Condo in Marco Island

4.94 out of 5 average rating, 64 reviews

*Fall/WinterSpecials* Amazing Beachfront 2/2 Condo

An outdoor area features a screened-in lanai with a heated saltwater pool, surrounded by a spacious deck. The pool is accented with turquoise tiles, and comfortable lounge chairs are positioned nearby, set against a backdrop of lush greenery and clear blue skies.

Home in Marco Island

4.85 out of 5 average rating, 34 reviews

Spacious Coastal Home w/ Pool, Hot Tub & Bikes.

The waterfront view showcases two distinct buildings set against a clear blue sky. Palm trees frame the scene, with docks leading to the water. The main house features large windows, while the adjacent building offers a charming contrast with its elevated structure.

Home in Everglades

4.94 out of 5 average rating, 33 reviews

Lostman's Lodge -Everglades City, Sunset View,Pool

Destinations to explore