Vacation rentals in Highland Lakes, Clearwater

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Top-rated vacation rentals in Highland Lakes, Clearwater

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy living area features a comfortable gray sofa adorned with decorative pillows. A wooden coffee table sits in front of the sofa, while a television is positioned on a media console against the wall. Natural light enters through a nearby window with blinds.

Townhouse in Clearwater

5 out of 5 average rating, 28 reviews

Close to honeymoon isl white sand clear beach! Fun

Few miles to downtown Dunedin, honeymoon island, beaches, close to mall. best restaurants! Huge 1 br 1 ba w front porch and screened room. A few miles to quaint safety harbor, pier, best shops and restaurants. See the manatees at pier swimming. Walk to the mall, shops, restaurants, movies. Not too far from tarpon springs sponge docks. Great fishing. Very quiet, only one neighbor close. 2 large beds. Huge bedroom, kitchen. open floorplan, pass through to dining room. Lowest $ on site! won’t last!

Top guest favorite

A spacious bedroom features a king-size bed with a stylish tufted headboard, draped in golden bedding. Two bedside lamps provide soft illumination. The room is complemented by modern tile flooring with a marble pattern, and a ceiling fan enhances comfort.

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 313 reviews

Private Suite, 1 bedroom, 1 bathroom, pool, patio

Private suite attached to Large house located in Palm Harbor with king-size bed, Split unit A/C Amenities include: Large Bathroom with Jacuzzi, Walk-in Shower. Access to shared pool and patio, backyard and Sundeck. Room includes refrigerator/freezer, Microwave, Coffee maker, Iron and kitchenette. Bistro set in room. Private entrances to room and patio/backyard. No shared space. Cable TV, Streaming and Wi-Fi . Centrally located to Restaurants and shopping. 10 mins. to the beach/Pinellas Trail.

Guest favorite

A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.

Guesthouse in Palm Harbor

4.89 out of 5 average rating, 146 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

Top guest favorite

A two-story beach-style house is depicted, featuring a covered porch with white railings and blue shutters on the windows. Potted plants adorn the porch, complementing the light exterior. Lush greenery is visible in the background, providing a tropical ambiance.

Home in Dunedin

4.98 out of 5 average rating, 296 reviews

Walk Downtown & to Waterfront Designer Home for 8

Experience the charm of the Barefoot Parrot House, a spacious home with beautiful designer coastal decor and abundant outdoor space. Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches - Honeymoon Island and Clearwater Beach. Walk, bike, or cart to stunning sunsets, restaurants, breweries, shops, and the Pinellas Trail. Perfect for families, couples, small groups. Loaded with beach gear, kids's items and games. Treat yourself and book today!

Guest favorite

The outdoor area features a heated pool with crystal-clear water, surrounded by a screened lanai. Comfortable lounge chairs are placed nearby, providing ideal spots for relaxation. Tropical plants enhance the space, framing a serene environment perfect for swimming and sunbathing.

Home in Palm Harbor

4.91 out of 5 average rating, 114 reviews

Heated Pool, 10 min to Beach, Close to Restaurants

Welcome to Turtle House! Perfectly situated in the heart of Palm Harbor lies this gem. Enjoy a completely renovated private heated pool, and with a quick and convenient access to US19 enjoy shopping, restaurants or local beaches. Perfect for families, couples, and anyone who needs the space to spend time together or enjoy some privacy for enjoyment and relaxation. 10% discount for Military, First Responders, Teachers, friends and family - book & message me, I'll apply the discount, that's it!

Top guest favorite

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

4.98 out of 5 average rating, 117 reviews

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Top guest favorite

A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.

Home in Palm Harbor

4.99 out of 5 average rating, 134 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

Top guest favorite

A spacious primary bedroom features a comfortable bed with neutral bedding and softly colored walls. Light enters through large windows adorned with sheer curtains, creating a bright and airy space. A modern lamp provides additional lighting beside the bed.

Home in Dunedin

4.96 out of 5 average rating, 141 reviews

Dunedin 5 STAR! Heated POOL+10 Mins to Beach

This Modern Coastal home is the perfect vacation spot! Recently renovated 3br home located just a few minutes from downtown Dunedin and some of the best Gulf Coast beaches. Take a dip in our heated saltwater pool, or relax on the screened-in patio with a cup of coffee. The open concept design creates a relaxing atmosphere with all the necessary amenities. Conveniently located near excellent dining options, shopping, Blue Jays stadium, and the waterfront. Make unforgettable memories.

Top guest favorite

A welcoming facade of the house features a covered entrance with a porch, flanked by landscaped greenery. The smooth concrete pathway leads to a dark front door, and a single-car garage is visible on the right, surrounded by well-maintained grass.

Home in Barrington Hills

5 out of 5 average rating, 13 reviews

Coastal Calmness

Minutes from down town Dunedin, amazing beaches, restaurants and places of interest, welcome to Costal Calmness! This renovated open plan 3 bedroom, 2 bathroom house has a fenced in yard in a family friendly neighborhood. This home has an open kitchen with an island, large dining area and stainless steel appliances. An open family room awaits with a smart 65" TV ready for your streaming network of choice. Relax outside with a beverage in the screened in lanai.

Top guest favorite

The modern kitchenette features sleek cabinetry, a stainless-steel refrigerator, and a countertop with three black bar stools. A flat-screen television is positioned nearby, and natural light is observed reflecting off the tiled floor, enhancing the open layout.

Apartment in Clearwater

4.99 out of 5 average rating, 190 reviews

Welcome to your cozy studio!

This charming furnished studio apartment is the perfect blend of comfort and convenience, offering everything you need for a delightful living experience: *Fully Furnished *Comfortable Sleeping Area *Equipped Kitchenette *On-Site Laundry Room *Private Parking Space *Private Patio Prime Location: Conveniently located close to shops, restaurants, parks and just 10 minutes away from the breathtaking Clearwater Beach

Superhost

A well-appointed sleeping area features a spacious bed with crisp white linens and a gray quilt. Flanking the bed are two wooden nightstands, each topped with a softly glowing lamp. Above the bed, two framed art pieces complement the simple decor, while a woven wall hanging adds texture.

Hotel room in Dunedin

4.84 out of 5 average rating, 268 reviews

Seaside Artisan Apartment 2

This Airbnb offers a unique experience to stay at a mom and pop style retro motel. There is no lobby for the guests. However, we do rent the owner suit with front desk on airbnb as well. You can find it under “Seaside Artisan Motel Owner Suit”. This Airbnb is walking distance from the restaurants, shops and bars in Dunedin. It’s about 4 miles away from Honeymoon Island and about 6 miles from Clearwater Beach.

Guest favorite

A spacious living area is highlighted by two comfortable sofas adorned with decorative pillows. A coffee table occupies the center, while soft lighting enhances the ambiance. Large windows provide views of the outdoor area, allowing natural light to brighten the space.

Home in Clearwater

4.88 out of 5 average rating, 192 reviews

The Dolphin House Clearwater. Smart TV, Cable

This 2-bedroom, 2-bathroom home is 6 miles from Clearwater Beach, voted America's #1 Beach. Local favorite downtown Dunedin is 2 miles away with shops, breweries, waterfront trails, and more. Quiet location convenient for trips to beaches, restaurants, parks, shopping, dining, and nightlife. Fully fenced yard with charcoal grill. This home has 2 washers and 2 dryers perfect for up to 8 guests.