Holiday rentals in Highland Lakes

Modern Private Estate | Central to Tampa & Beaches

Experience this private 1-acre, modern home designed for space, calm, and everyday comfort. Surrounded by mature oaks and palms, this serene property offers rare privacy just minutes from Tampa Airport, Clearwater Beach, Safety Harbor, St. Pete, and top attractions. Enjoy a chef’s kitchen with modern appliances, spacious living areas, and peaceful outdoor spaces with a patio, electric grill, and koi pond. Ideal for families, longer stays, & guests who value tranquility, and a thoughtful design!

Escape, explore, tranquility, frappé

"Enjoy Hotel-Quality Comfort at Airbnb Prices — Minutes from Clearwater Beach, Dunedin & Safety Harbor. Conveniently located next to US-19, providing easy access throughout all Tampa Bay area: airports, beaches, and major attractions. Quiet neighborhood Spacious outdoor area Comfortable beds and premium linens Fully equipped kitchen Washer & dryer 2 or more shaded parking spaces We created this space with one goal in mind: making your vacation enjoyable. We are a text away for any need/question

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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 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.

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8

Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to gorgeous sunsets, shops, dining, breweries, and Pinellas Trail. Perfect for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this Dunedin favorite!

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.

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! Please note that the minimum age requirement to book is 23.

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 75.00 fee. 6 mi to honeymoon Walkable to grocery bars, restaurants. This is certified .

Clearwater Studio Getaway

Welcome to Clearwater Studio Getaway! Enjoy a peaceful and centrally-located space just 15 minutes from Clearwater Beach, Downtown Clearwater, and the Tampa Bay área .Just 7 minutes from Safety Harbor and 14 minutes from Dunedin . Perfect for travelers or couples, this cozy studio features a private bathroom, comfy bed, and essential amenities. Relax after a day of sun and fun, with shops, dining, and attractions all within easy reach. Your perfect Florida stay!

Palm Harbor Pet-Friendly Retreat Near Honeymoon Is

This newly renovated and peaceful Duplex-home in Palm Harbor offers a spacious layout perfect for families to gather and relax. Centrally located, it is just a short distance from popular Cities, restaurants, bars, shopping malls, and more. Only twelve minutes from the famous city of Dunedin and Tarpon Springs, 25 minutes to the renowned Clearwater Beach, and 20 minutes to Tampa International Airport, making it an ideal spot for both relaxation and adventure

Checkmate Cottage | Fire Pit + Putting Green

Escape to this fun-filled Palm Harbor retreat featuring a private backyard oasis with a fire pit, life-size chess, putting green, and café lights for cozy evenings outdoors. This stylish 2BR home sleeps 6 with a queen sized pull out couch and offers a peaceful central location near Honeymoon Island, Dunedin, the Pinellas Trail, and Gulf beaches. Perfect for couples, friends, or small families looking to relax, play, and explore Florida’s Gulf Coast.