Holiday rentals in Highland Lakes

Historic 1922 Home • Walk to Downtown & Blue Jays

Stay in a beautifully preserved 1922 Dunedin home passed down through 6 generations. Walk to downtown, restaurants, breweries, the marina, and the Trail. With 3 full bathrooms, and a prime location, this home offers character, and convenience What sets this home apart is its rare combination of location, space, and history — something you simply won’t find in typical vacation rentals. Thoughtfully maintained, this home offers a more elevated and memorable stay than standard listings in the area

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

Walk to Downtown and Waterfront - Private Yard

Steps to Main Street and minutes to beaches, yet tucked away on a quaint street. Private yard with grill in a 100 % prime location. Walk to restaurants, breweries, shops, and live music. Walk to stunning sunsets or drive minutes to award-winning beaches such as Honeymoon Island, Caladesi Island & Clearwater Beach. Designer decor. Sleeps 6. Two king bed suites and a luxury couch that sleeps 2 more. Fully loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today.

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

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. This is certified .

WOW! Dunedin Coastal POOL Home-beaches-eateries

Escape to this newly remodeled 3-bedroom Dunedin vacation home, perfectly located just minutes from downtown Dunedin & some of the Gulf Coast’s best beaches. Enjoy a refreshing dip in the heated pool or relax on the spacious screened-in lanai. The open-concept design offers a bright, comfortable space with all the amenities. Close to great dining, shopping, the Blue Jays stadium, & the waterfront. Great for families and friends to relax, connect, and make unforgettable memories together.

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.

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.

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!

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!

Tropical Oasis Retreat w/ Heated Pool

Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome