Holiday rentals in Saint Joseph Sound

Surf Shack Tiny Home on Pinellas Trail w/ Heated P

Welcome to the Dunedin Tiny House Vacation Rentals! This Vacation Rental property offers daily, weekly or monthly rentals in 4 luxury tiny homes, a 3 bed bungalow & 1 bed cottage. The 6 Units along with a large Heated Pool are all tucked away within a thoughtfully planned, peaceful & wooded lot.... located right on the Pinellas Trail! The front entrance is conveniently located on Bayshore Blvd just north of the crossroad of Wilson. Once you enter the front door of your unit you will enjoy a

The Palm Haus • Heated Pool • Near Beach • Games

Charming home with stylish baths & bedrooms. Heated pool included in the price. Gas fire-pit, outdoor games, large secluded backyard! Game room! Near Honeymoon Beach & Caladesi Island open for sunbathing & water sports; 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.

Walk Downtown and to Waterfront, Mins to Beaches

Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater Beach, this stylish upstairs 2-bedroom cottage blends modern coastal design with exceptional comfort. Tropical murals, treetop views, two king beds, and a sleeper sectional create a chic and indulgent stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s gorgeous waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

Welcome to Seaside Sanctuary 🌊🌅 – Your Ultimate Waterfront Escape Nestled in charming Crystal Beach, this spacious 4-bedroom, 2.5-bath retreat perfectly blends luxury, comfort, and coastal fun. Go kayaking from your direct Intracoastal access, soak in unobstructed sunsets, relax in the hot tub, challenge friends in the game room, or grill a delicious meal on the patio 🥙. Perfect for family reunions, bestie getaways, wedding weekends—or simply because you deserve a seaside escape!

Guesthouse with Pool in Palm Harbor

This beautiful Guest house was completed in August 2024 and is located in the back corner of a 1/2 acre lot with all the amenities for a short stay or longer stay. From private access to the house and use of the shared pool and patio this house has it all! Full Kitchen, Dining Area, Living room, Washer and Dryer. Stunning Master Bedroom, Master Bath with Dual Vanity, Jacuzzi and walk in shower and spacious master closet. This Gem includes all the amenities for a Luxurious Stay!

Cozy Retreat! Walk to Crystal Beach/Park

Cozy Crystal Beach Retreat – Pet Friendly Enjoy this charming 2BR, 1BA home with queen beds and a pull-out sofa. Pets welcome with fee! Relax in the fully fenced backyard with picnic table, perfect for outdoor meals or your furry friend to play. Walk to the water or explore the nearby Pinellas Trail. Just minutes to downtown Dunedin (7 mi), Honeymoon Island (7.5 mi), Clearwater Beach (13 mi), and Tampa Intl Airport (22 mi). Ideal for couples, families, or a relaxing getaway!

Seaside Artisan Apartment 6

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.

Honeymoon Luxury Residence with Heated Pool &Sauna

Heated pool, features European-designed interiors, sauna, 100" theater, latest Xbox, gym, and smart TVs in every bedroom. Chef’s kitchen, dining for 12 ideal for celebrations, outdoor gazebo with fireplace & innovative grill, lush tropical landscaping and breathtaking sunset views. Easy access to beaches, marinas, Dunedin, Tarpon Springs, and Clearwater dining & nightlife. Safe, prestigious neighborhood — perfect for family fun or romantic escapes.

Gulf View on Bay: Newly Renovated

Your cozy getaway awaits in Palm Harbor at this enchanting house. Great view of the Gulf from the living room, back porch and upstairs bedroom. Nice relaxing front deck with rocking chairs. With two spacious bedrooms featuring king beds and a living room that includes a twin bed pullout, guests have plenty of room to relax. The two bathrooms offer both a soothing bathtub and a refreshing shower, perfect for unwinding after a day of adventure.

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Welcome to Island Oasis, your waterfront paradise in Palm Harbor, FL! ☀️🌊 This 3BR, 2BA retreat sleeps 8 and is minutes from Dunedin, Tarpon Springs, and Honeymoon Island. Start your day with coffee on the private dock, explore beaches or bike the Pinellas Trail, then unwind with stunning sunsets over the water. Perfect for families, couples, or friends—come experience true island life in your own slice of paradise! 🌴

Pvt Pool, Free Kayaks, Wlk to Gulf, Fish, Bike Trl

Escape to your private Palm Harbor oasis! This studio, offers complete privacy with a cozy queen bed, sofa bed, and kitchenette. Enjoy the sparkling in-ground pool reserved for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or explore the nearby Pinellas Trail. Enjoy beaches, dining, breweries, and live music minutes away. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.

Private pool, Golf Cart, Completely Renovated!

Discover the ultimate retreat in a central location! Golf cart to Down town, restaurants, breweries, parks, and trails! Multiple beaches with-in a 10 minute drive. This thoughtfully equipped home is an oasis of leisure, offering a pool, games, and a fully-equipped kitchen. Optional Golf cart rentals, private boat rides and fishing trips add to the excitement. Book now for an unforgettable experience!