Pet-friendly holiday rentals in Holiday

Golf Cart, Kayaks, Pedal Boat Included •Waterfront

Welcome to Azalea by the Sea, your perfect vacation escape! Enjoy endless water activities and relaxation right in your own backyard. Highlights You’ll Love: •🛶 Kayaks for exploring the waterways •🌊 Water Mat for fun on the water •🔥 Fire Pit for cozy evenings under the stars •🎯 Cornhole Boards for friendly competition •.🚗 Golf Cart •🌿 5 Minutes to Weeki Wachee River — perfect for kayaking, paddleboarding, or spotting manatees •🎵 Nearby Bars & Restaurants with live entertainment every night!!

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘tiny-house’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This brand new luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 1G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

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

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Our Gemini Place: Comfort & Charm in Old Tarpon

Welcome to Gemini Place, a cool, quiet 2/2 filled with an easy charm. This solid 1,100- sq. ft house is in the heart of old Tarpon and is a perfect, simple escape for a few days, a few weeks or longer. The north-facing house sits on a one-way brick street and is an easy walk to everything in this quaint, Greek-flavored town. We are close to some of the best beaches in the U.S. We're pet friendly but do have restrictions and a fee that is determined by several factors. Please inquire.

Driftwood Surf Shack

This unique Surf Shack is a guest home that sleeps up 4 & still plenty of room to relax inside or outside on the large wood deck situated under a beautiful oak tree. Located in the historic district Tarpon, just blocks from Downtown, the famous Sponge Docks & Craig Park where you can watch dolphins feed at sunset in the many Bayous. Close to beaches, shopping, restaurants, breweries, boat excursions, water sports & the Pinellas Trails you will never get bored in this town!

5 mi to Tarpon & Beaches• House with Heated Pool

Oasis with a private pool heated Nov–Mar and a patio, 5 miles from Tarpon Springs, near Dunedin and a short drive to Clearwater/Tampa. Perfect for family or friends: fast Wi-Fi, workspace, fully equipped kitchen, and BBQ. 24/7 self check-in and on-site parking. Quiet for restful nights; beaches and parks minutes away. Note: pool heating available November–March (weather-dependent). Last-minute promos active. Book today!

Tiki Hut Cottage

This unit private vacation rental is privately located on the property, plenty of space for 4 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Spacious living area with a kitchenette. The property is an acre of lush tropical plants Conveniently located to the downtown & beach.All our units are non-smoking and vaping.

MODERN/Mins to Beach/walk to dwtn/Free parking

🌴 Escape to Tarpon Springs! This newly renovated 1B/1B private home is perfectly located—just 5 minutes to the beach and the famous Sponge Docks, and a short stroll to charming downtown. Whether you’re here to relax, explore, or soak in the local culture, this getaway puts you right in the heart of it all.

Modern 3 Bedroom 2 Bathroom House

Experience the charm of Tarpon Springs from our newly renovated 3-bedroom, 2-bathroom family retreat. Just minutes from Lake Tarpon and a short drive to the iconic Sponge Docks, authentic Greek eateries, Fred Howard Beach, the Pinellas Bike Trail, and countless other local gems.