Vacation rentals in Highland Lakes

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Top-rated vacation rentals in Highland Lakes

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

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Guest favorite

A charming Florida bungalow features a turquoise exterior with natural stone accents. The front porch is accessed by a concrete pathway lined with greenery, including tropical plants. A small entry door and window allow for natural light, framed by neatly placed shutters and landscaping.

Home in Barrington Hills

4.91 out of 5 average rating, 268 reviews

Wonderful family friendly home in Dunedin FL

Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caledesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.

Top guest favorite

Guesthouse in Palm Harbor

4.97 out of 5 average rating, 333 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.

Superhost

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

4.87 out of 5 average rating, 156 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 spacious living area is furnished with a large, L-shaped gray sofa, providing comfort for relaxation. A flat-screen television is mounted on the wall opposite the sofa, while natural light enters through two windows, dressed with light curtains. A decorative rug and a console table add to the inviting ambiance.

Place to stay in Dunedin

4.96 out of 5 average rating, 137 reviews

The Zen Den Studio

Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

Top guest favorite

Home in Palm Harbor

5 out of 5 average rating, 77 reviews

Luxury Home + 10 min to Beach + Htd Pool + Firepit

Renovated home with stylish baths & bedrooms. Gas fire-pit, pool, outdoor games in the backyard filled with beautiful greenery! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports. Near historic downtown Dunedin with cute shops, cafes, restaurants & cultural events. The area has a number of top-notch golf courses and trails. Palm Harbor's welcoming community & mild climate make it an ideal getaway for outdoor adventures, cultural experiences, and coastal views.

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

4.99 out of 5 average rating, 137 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

Superhost

An outdoor seating area is sheltered by a wooden pergola adorned with string lights. A cozy couch is positioned on a decorative area rug, complemented by a small table. Lush greenery surrounds the space, providing a tranquil environment for relaxation.

Guesthouse in Dunedin

4.84 out of 5 average rating, 125 reviews

Guest House in prime location!

This special place is close to everything, making it easy to plan your visit. Less than 30 minutes to TPA Airport, 13 miles to Clearwater Beach, 2.2 Miles to Honeymoon Island, 1.0 miles to US-19 to easily get to surrounding areas, and 3.5 miles to downtown Dunedin. Guest house located on property with friendly host. There is one parking space provided for guests onsite. Happy to provide recommendations for a local experience during your stay! Beach necessities available upon request.

Top guest favorite

A cozy living area showcases a modular blue sofa, adorned with soft pillows and a warm throw. A light wooden coffee table rests in the center, complemented by decorative items. Natural light enters through a window, creating a bright and welcoming atmosphere.

Cottage in Dunedin

4.99 out of 5 average rating, 346 reviews

Walk to Downtown and Waterfront - Private Yard

Private yard with grill and concrete construction makes this beautiful cottage feel like a private oasis. Steps from Main Street Dunedin and a short walk to stunning sunsets at the waterfront. Easy access to restaurants, breweries, shops, live music. Beachy stylish modern décor & open floor plan. A quick drive to award-winning beaches like Honeymoon Island and Clearwater Beach. The perfect getaway in delightful Dunedin—come be our guest at the Barefoot Parrot Cottages.

Guest favorite

A well-appointed room showcases a spacious bed with soft linens against a light-colored wall. Natural light streams through multiple windows, enhancing the comfortable seating area featuring a gray sofa and small white dining table. A touch of greenery is added with a potted plant.

Hotel room in Dunedin

4.74 out of 5 average rating, 235 reviews

Seaside Artisan *Dog Friendly* 5

This Airbnb offers a unique experience to stay at a mom and pop style retro motel. The property has total of 10 airbnb’s. There is no lobby for the guests, however we do list for 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 light green room features a queen-size bed with a white quilt and decorative pillows. A small dining area with a round table and two chairs is visible alongside a neutral-toned sofa. Large windows provide natural light, and indoor plants are seen through the glass doors.

Guesthouse in Clearwater

4.88 out of 5 average rating, 222 reviews

Cottage on Pinellas Bike Trail

This cottage on the trail is a gem. It is an easy one mile bicycle ride to downtown Dunedin and a quick stroll to waterfront Edgewater Park to watch sunsets or see the lights of Clearwater Beach across the intracoastal waterway. Circular driveway with a carport for off street parking. The cottage is equipped with a Keurig, microwave, mini fridge, as well as beach amenities and wifi. There's a fenced back patio for you to enjoy our beautiful weather!

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, 203 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

Guest favorite

A modern bedroom features a spacious bed with grey upholstery and decorative pillows. Two bedside tables with lamps are positioned on either side of the bed. Framed artwork hangs above the bed, and a stylish table is placed nearby, accentuated by a small plant.

Guest suite in Clearwater

4.91 out of 5 average rating, 234 reviews

Home away from home!

This 1 bedroom guest house in Clearwater, is truly a fantastic retreat. Feel at home with all the amenities. Great location, safe surroundings, fenced private courtyard for smoking, 5 miles from Clearwater beach. Affordable, queen bed, kitchen, shower, Netflix, free driveway parking on premise. Thoroughly cleaned after every guest check out. Come and enjoy in this beautiful city.