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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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, 324 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.

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, 338 reviews

Walk to Downtown and Waterfront - Private Yard

Bright and beachy with stylish modern décor and an open floor plan. Concrete construction, a private yard, and a gas grill makes this cottage feel like your personal oasis. Steps from Main Street Dunedin and a short walk to the water. Enjoy gorgeous sunsets and easy access to restaurants, breweries, shops, and live music. 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.

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, 129 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

A well-lit bedroom features a spacious white bed with crisp linens and a decorative bedside lamp on a nightstand. A ceiling fan adds to the comfort, while windows with shutters allow natural light. The open doorway leads to a hallway, hinting at additional living spaces.

Home in Clearwater

4.84 out of 5 average rating, 44 reviews

Spacious 3BR, Central Location MD.BNB-Indigo(6G)

Welcome to your tropical oasis! This charming 3-bedroom, 3-bathroom home is your gateway to a vacation filled with unforgettable experiences. Just 30 minutes away, discover some of the finest beaches in Florida, an exciting array of world-class entertainment, and a plethora of extraordinary activities. After a day of adventure, retreat to the serenity of your own private, fully fenced backyard. Embrace the perfect blend of relaxation and exhilaration. Don't miss out-reserve your stay now!

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

4.83 out of 5 average rating, 121 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.

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, 146 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 screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.

Home in Palm Harbor

4.95 out of 5 average rating, 157 reviews

Tropical Getaway w/Heated Pool & King Beds

Welcome to our sun-kissed getaway in sunny Palm Harbor! You'll find a fully stocked kitchen, a private heated pool, and comfortable accommodations for up to 6 guests. Whether relaxing on one of our award-winning beaches, playing a round of golf, or exploring Tampa Bay's fun spots, there's something for everyone to enjoy. Just a quick note: Because of a family member's allergies, we're not able to allow any animals on the property, including ESAs. Thanks so much for understanding!

Guest favorite

A screened-in outdoor area features a heated pool and spa accompanied by a spacious dining table set for eight. Vibrant glassware and dining plates are arranged, capturing bright colors against the backdrop of lush greenery and a clear sky.

Home in Dunedin

4.93 out of 5 average rating, 110 reviews

Luxury home ~ Heated pool, hot tub, TWO kitchens

Welcome to this stunning 5-bedroom home, located in a quiet, family-friendly neighborhood, just minutes from quaint Downtown Dunedin and a short drive to both Clearwater Beach and Honeymoon Island Beach! 5 bedrooms, 3 bathrooms - including a full "in-law" suite downstairs with it's own full kitchen and living room! It's everything you need and more ♡ Enjoy a heated pool (84°), hot tub, BBQ grill... need we go on? Feel free to ask any questions. We look forward to hosting you!

Superhost

A spacious living area features a large sectional sofa in a calming blue tone, complemented by a glass coffee table. Wall-mounted shelves hold decorative items, and light streams in from the nearby window. The open layout leads into the dining space, enhancing the inviting atmosphere.

Home in Dunedin

4.74 out of 5 average rating, 27 reviews

Casual, relaxing 2/2 SFH remodeled, in Dunedin.

Forget your worries in this spacious and serene space. The Bluebird house is located in a super quiet neighborhood. This 2/2 ranch style offers a big backyard. Enjoy your private driveway and garage. Nicely appointed with everything you will need to enjoy your stay. Granite, stainless appliances, cotton linens and towels. Keurig coffee maker. Enjoy your privacy! 2 DOGS ARE ALLOWED FOR A FEE. 6 mi to honeymoon 2 mi to dunedin Walkable to grocery bars, restaurants.

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, 198 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 living area showcases a sleek gray couch featuring soft tufting and a white decorative pillow. A circular wooden coffee table, supported by a geometric metal base, rests nearby, providing a casual yet stylish touch to the space.

Home in Palm Harbor

4.89 out of 5 average rating, 212 reviews

Cute Lil' House Near Historic Downtown Palm Harbor

They say that the best things come in small packages. Well that certainly rings true in this case. Our house may be small, but it is large on personality and full of elegant charm. Newly remodeled and filled with personal touches, this small package is ready to be your Florida retreat. Enjoy charming palm harbor on our golf cart for a small rental fee.