Vacation rentals in Holiday

The exterior of the retro home features a gravel driveway bordered by illuminated garden lights, creating a welcoming ambiance. Two front doors are framed by windows, and potted plants add a touch of greenery. A white fence encompasses the property, enhancing its charm against a twilight sky.

4.95 out of 5 average rating, 192 reviews

King Bed Luxury & Queen 2/1/1—Patio+Laundry+3TVs

Transport back to the 50’s when staying at this coastal retro 2 BD/1BA home. The charming mid-century design throughout boasts top-of-the-line amenities including 3 Roku Smart TV’s, a fully equipped kitchen, a delightful King & Queen mattress, a dedicated workspace, an enclosed garage, outdoor patio, beach towels, a washer & dryer. Indulge in all the luxuries while being near Tarpon Springs/Sponge Docks(4.9mi) Anclote Beach(4.8mi), Honeymoon Island State Park(16.2mi), several restaurants & more!

A comfortable living area features a beige sofa adorned with orange accent pillows, flanked by two stylish lamps. A round wooden coffee table is positioned on a decorative rug, with modern wall art enhancing the space. A red armchair adds a pop of color to the setting.

4.94 out of 5 average rating, 108 reviews

Cozy 3-bed home close to beautiful beaches.

Newly updated 3-bedroom, 2-bath home close to everything. Centrally located, within 20-30 mins to the famous Tarpon Springs Sponge Docks, Sunset, Howard Park, Honeymoon Island, Anclote River Park & Clearwater Beaches, Busch Gardens Theme Park and Weeki Wachee. Close toTampa International Airport. Numerous country club golf courses, waterfront restaurants/bars within a short drive. Enjoy your home away from home with everything you need and more with a BBQ Grill/ Fire pit and other amenities.

4.96 out of 5 average rating, 96 reviews

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

Home in Forest Hills

Paradise!Renovated waterfront pool home.Sunsets!

No hurricane damage!Sunsets to die for! Completely remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard &sometimes you can spot dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops.New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys that you can take to the beach.Bonfire pit.Grill.Heated pool for a fee. Come,relax&enjoy

A patio area is visible featuring a round table with chairs, surrounded by decorative plants. Kayaks are propped against the railing, while the shimmering water of the canal flows in the background, framed by palm trees and bright blue skies.

4.99 out of 5 average rating, 87 reviews

Nature Lovers Retreat

Relax and enjoy! Welcome to your 3 bedroom 2 bath vacation home. Newly renovated well equipped kitchen, new appliances and laundry room. Perfect for couples or families to make great memories. You can fish, kayak, paddleboat or just sit back and enjoy nature from our dock on Lake Connelly. Very centrally located in the Tampa Bay area and are close to plenty of things to do: Tarpon Springs Sponge docks, Dunedin, Safety Harbor, St. Pete, Honeymoon Island, Fred Howard Park and more

5 out of 5 average rating, 267 reviews

A vintage windmill stands gracefully among lush trees, surrounded by fallen leaves. In the foreground, a cozy bed is visible, adorned with green accents and soft bedding, conveying a serene atmosphere. Natural light filters through the foliage, enhancing the tranquil setting.

Apartment in Timber Oaks

The Bohemian Studio: Separate Entry & Fenced Patio

🚨 Unbeatable Deal-A serene, countryside escape, BEST PRICE IN THE AREA. This cozy studio offers total privacy, separate entrance & self check-in Great location, minutes away from hospitals, restaurants, springs & beaches 30 min from Tampa Bay Area 🌳 2 Acres & Fenced Patio 🍳 Fully Equipped Kitchen & bathroom 💻 High-Speed Internet, ethernet & FREE Netflix 🚗 FREE Parkings Perfect for traveling nurses, snowbirds or romantic escapes The best of both worlds Comfort, Peace & Privacy

4.91 out of 5 average rating, 134 reviews

A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.

Home in Forest Hills

Sunny Pool Home • Near Tarpon & Beaches 5 mi

🌴 Heated private pool oasis (Nov–Mar) 5 mi to Tarpon Springs—ideal to recharge. 🏡 Private patio for BBQ and outdoor time in a quiet area for great sleep. Perfect for families & friends: fast Wi-Fi + workspace, fully equipped kitchen, 🔑 24/7 self check-in, and 🚗 on-site parking. Easy access to Dunedin, Clearwater, Tampa, and beaches (times vary with traffic). ✨ Note: pool heat available Nov–Mar (weather permitting). ⏳ Last-minute promos active—book and lock in your dates!

4.97 out of 5 average rating, 92 reviews

Guest suite in Holiday

Private Apt near to Fred Howard Beach| Big Parking

Private & cozy apartment with independent entrance and free parking for two vehicles. Located in a quiet and safe area just minutes from the beach and Tarpon Springs (“Little Greece”) and just minutes from Fred Howard Park Beach.Enjoy a fully equipped kitchen, comfortable bedroom with work desk, Smart TV, fast WiFi, spacious bathroom, and outdoor terrace. Perfect for couples, small families, or remote workers Scan the QR in the last photo for a full video tour

A sparkling saltwater pool is featured in the backyard, with a gently curving shape and a clear blue surface. The area is fenced for privacy, with a well-maintained lawn and a sunny sky visible above.

4.96 out of 5 average rating, 105 reviews

Private 3 Bedroom House w/ Heated SaltWater Pool

Spend your holidays in HOLIDAY, FL! We welcome you to our cozy, fully renovated house with a large, heated private in-ground, SALTWATER pool. The house has three bedrooms and enough room for 7 guests, along with two full bathrooms. The kitchen is stocked with all cookware essentials needed. The house has everything you need for vacations, so you may kick back and relax. It is centrally located to many attractions if you're up for a drive.

A vibrant landscape features lush green grass and tropical plants, with a palm tree and bushes in view. A small body of water reflects the blue sky dotted with clouds. An American flag is positioned near a white railing, adding a charming touch to the scene.

4.95 out of 5 average rating, 39 reviews

Relaxing Lake House

Take it easy at our tranquil getaway. Observe local and migrating birds right from the backyard, fish from the dock, or just relax and enjoy the view from the screened in porch. Minutes from New Port Richey and Tarpon Springs famous Sponge Docks and less than an hour from all the Tampa attractions and Clearwater Beach. Take a day hike at Honeymoon Island Osprey and Pelican Trail and end the hike with a swim at the beach.

An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.

4.93 out of 5 average rating, 108 reviews

Lakefront Paradise with Heated Saltwater Pool

Discover lakeside bliss at this 2-bedroom retreat with a private pool, dock, and outdoor fire pit. Enjoy stunning waterfront views, relax by the pool, or gather around the fire under the stars. The bedrooms offer a cozy haven, and the fully equipped kitchen ensures convenience. Just minutes from pristine beaches, this retreat provides the ideal balance of relaxation and recreation. Your perfect lakefront getaway awaits!

Guesthouse in New Port Richey

An outdoor seating area is situated on a lawn, featuring a small black table and two chairs. The view includes the serene Pithlachascotee River, along with a dock and decorative features, framed by lush trees and greenery.

5 out of 5 average rating, 197 reviews

Palm Hideaway on the Cotee River

Relax on the river at Palm Hideaway-a luxury escape to the Gateway of Tropical Florida. Our cozy guest cottage is nestled amid lush greenery on the Pithlachascotee "Cotee" River in New Port Richey. Sleep in the king size bed & have coffee or tea on your Tiki patio rain or shine. Guests have shared access to the river from the park-like backyard & can enjoy the fire pit or paddle the kayaks.

4.93 out of 5 average rating, 105 reviews

A welcoming entryway features a sliding barn door that leads to a cozy sleeping area. A small table with four black chairs is positioned against the wall. Soft lighting illuminates the space, while decorative elements, including artwork and plants, add charm.

Apartment in Holiday

Cozy apartment private retreat

Welcome to Your Cozy Retreat! Escape to our charming guest house. This beautifully decorated space offers a perfect blend of comfort and style, making it an ideal getaway for couples, solo adventurers, and business travelers alike. Amenities: Free Wi-Fi Air conditioning and heating Complimentary coffee. Towels and chairs Free parking on premises. Security Cameras

Popular amenities for Holiday vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Holiday's top sights

Anclote River Park

91 locals recommend

Tarpon Springs Aquarium And Animal Sanctuary

112 locals recommend

Key Vista Nature Park

33 locals recommend

Other great vacation rentals in Holiday

The image showcases a heated in-ground pool bordered by light-colored pavers, overlooking a calm canal. Docked boats and palm trees line the water's edge, reflecting under a clear blue sky. The well-kept lawn adds a touch of green to the serene waterside setting.

4.72 out of 5 average rating, 175 reviews

Gulf Harbors Getaway Home with Pool

Apartment in Tarpon Springs

An aerial view showcases a modern two-story house surrounded by water and greenery. A private boat dock is positioned in the foreground, along with a manicured lawn featuring a putting green and colorful kayaks. Solar panels are visible on the rooftop.

5 out of 5 average rating, 100 reviews

Waterfront studio w/Hot Tub and Putting Green

5 out of 5 average rating, 6 reviews

Endless Summer

5 out of 5 average rating, 5 reviews

Home in Palm Harbor

Gulf View on Bay: Newly Renovated

4.89 out of 5 average rating, 9 reviews

Home with access to the Gulf.

4.83 out of 5 average rating, 58 reviews

A neatly arranged sleeping area features a spacious bed adorned with grey bedding and a decorative pillow. Soft lighting from two bedside lamps enhances the ambiance, while a piece of abstract wall art adds a touch of color. A light-coloured rug complements the wooden flooring.

Apartment in Holiday

Holiday Peaceful Studio

The exterior of the home is showcased with a well-maintained lawn, bordered by a circular driveway. The facade features neutral stone and brick materials, with a welcoming entrance illuminated by soft outdoor lighting. A flagpole stands proudly at the front, adding a classic touch.

5 out of 5 average rating, 28 reviews

Deluxe 3bd/2ba w/Heated Pool