Holiday houses in Highland Lakes

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Top-rated holiday rentals in Highland Lakes

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

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Top Guest favourite

A light-filled living area is displayed, featuring a comfortable beige sofa paired with a striped ottoman. A wall-mounted television is positioned opposite the seating. Natural light pours in through a window dressed with soft curtains, creating a relaxed ambiance.

Guesthouse in Dunedin

4.97 out of 5 average rating, 73 reviews

Downtown Dunedin Getaway 1BD/1BA

Experience the best of Dunedin, FL in our charming 1BD/1BA upstairs unit, just 1.5 blocks from downtown! Bright and cozy, it features a fully stocked kitchenette, a comfortable queen bed, in-unit laundry, and a dedicated office space with Wi-Fi. Enjoy your morning coffee or evening relaxation on your quaint outdoor deck. Perfect for those who want to explore our picturesque beach town, spend the day at Honeymoon Island, or need a peaceful place to work. Ready to make your Dunedin stay memorable?

Guest favourite

A cozy living area is furnished with a grey sectional sofa featuring red accent pillows. A wooden coffee table occupies the center, complemented by a flat-screen TV positioned on a light wooden media console. Natural light filters through the window with white blinds.

Home in Clearwater

4.87 out of 5 average rating, 31 reviews

Clearwater Cottage # 2

Stay at the Beautifully renovated & Peaceful Clearwater Cottage. Experience the beauty of Clearwater Beach just 5 miles away with it's pristine sands & award-winning charm. Explore the natural wonder of Caladesi Island, Honeymoon Island or take a leisurely bike ride along the picturesque Pinellas Bike Trail. Discover the vibrant downtown areas of Clearwater & Dunedin each just mins drive away. Easy access to local amenities & attractions, your stay in this area will be nothing short of memorable

Top Guest favourite

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, 164 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

Guest favourite

A modern living room features a comfortable sofa and an accent chair. A large wall-mounted television displays a serene beach scene. A decorative table holds a small plant, and a piece of abstract art adorns the wall, enhancing the space's inviting atmosphere.

Home in Clearwater

4.91 out of 5 average rating, 106 reviews

Clearwater House!Near the beach!Newly renovated!

Enjoy your stay in this newly renovated home centrally located in the heart of Clearwater and the Tampa Bay Area! Family vacation, work conference, friends vacation, exploring Florida? Look no further! The home has everything you need for the perfect getaway including luxurious bedding to the max! Everything you need is within arms reach. #1 Beach in the country CLEARWATER BEACH only 20 min drive, TPA Airport 20 min away, charming Dunedin Downtown 15 min away and many more places to visit!

Top Guest favourite

A serene outdoor seating area features white adirondack chairs positioned on a natural stone patio, surrounded by lush green foliage and tropical plants. A glimpse of a swimming pool can be seen in the background, framed by additional seating and vibrant landscaping.

Apartment in Dunedin

4.94 out of 5 average rating, 122 reviews

Island Oak

This private vacation rental is a Second floor 1 bedroom apartment is newly furnished, professionally decorated and equipped with all the conveniences of home. Island Oak joins 4 other popular vacation rentals within the Grove Keeper Collective compound. This upper unit has a balcony off the bedroom which looks into a 175 year old oak that provides a tree house effect. We hope you come and enjoy this new addition to Grove Keeper Collective. All our units are non smoking and vaping.

Guest favourite

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, 164 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 favourite

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, 118 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!

Top Guest favourite

A spacious bedroom features a plush king bed with a light-colored blanket and two dark nightstands on either side. Vertical windows offer natural light, while neutral gray walls and wood flooring create a calm atmosphere.

Apartment in Clearwater

4.95 out of 5 average rating, 117 reviews

Relaxing beach gateway

Kick back and relax in this calm, stylish space.Only 5 miles from Clearwater beach! Newly renovated spacious studio with brand new bathroom and kitchenette! Spacious studio featuring 1 king bed, a fully equipped kitchenette , free 1 parking spot, high speed internet, flat screen TV. Quiet area located 5 min away from downtown Clearwater and steps away from beautiful park. There is also a dog park 5 minutes away. No smoking No parties Pets allowed 2 parking spot available

Guest favourite

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

Home in Palm Harbor

4.91 out of 5 average rating, 151 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today and experience the tranquility of country living!

Top Guest favourite

The retro-style home is set back in a spacious driveway, framed by palm trees and lovely landscaping. A classic red pickup truck is parked in front, with a fenced yard visible to the side. A clear blue sky complements the inviting atmosphere of the property.

Home in On Top of the World

5 out of 5 average rating, 89 reviews

Florida Retro AIRBnB

This Retro airbnb is minutes from the famous Clearwater beach. This 1960s home will bring you back to the greatest time in history. The entire retro era is right here in this unique fully fenced home. Dine around the table and venture back to the 1950s. Enjoy the 1970s and paint your own peace sign or flowers on the fence. Then enjoy the 1980s vibe in the new bathrooms. Dance the night away to the juke box. Don't forget to leave your mark on the chalkboard wall.

Top Guest favourite

A comfortable living area features a gray sectional sofa adorned with decorative pillows, paired with a cozy armchair. A glass coffee table sits on a patterned area rug, with a potted plant adding a touch of greenery. Natural light is visible from an adjacent room.

Apartment in Dunedin

4.98 out of 5 average rating, 102 reviews

In Downtown-Porch-Parking-603Mbps-Kitchen

Historic Home in the heart of Downtown Dunedin, known by locals as the Yellow House. First floor 2 bedroom apartment is tastefully decorated, clean and ready for your stay! Walk just a few steps to restaurants, bars, shops, and the Pinellas Trail. Home overlooks Pioneer Park where you can enjoy the local farmers market on weekends, concerts, movies, art festivals and much more, or just relax and watch the action from the front porch.

Guest favourite

The spacious living room is furnished with a light grey sofa and a pullout couch, accompanied by a modern coffee table. Natural light is welcomed through multiple windows, while a ceiling fan adds comfort. Artwork adorns the walls, creating an inviting ambiance.

Home in Palm Harbor

5 out of 5 average rating, 15 reviews

Palm Harbor Retreat | 2BR/1BA Near Gulf Coast Fun

Welcome to your Palm Harbor Escape! Perfectly positioned for sun‑soaked island beaches, charming Dunedin outings, and lively Tarpon Springs events, this home is designed for memorable stays. Families will love the flexible sleeping options, while foodies enjoy the fully stocked kitchen. With abundant parking—including RV space with a 125V hookup—you’ll have comfort, convenience, and adventure all at your doorstep.