
Vacation rentals in Holiday
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Top-rated vacation rentals in Holiday
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

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.

Waterfront studio w/Hot Tub and Putting Green
Studio Apartment on ground level. Direct access to Gulf of Mexico w/short boat/kayak ride. Queen-size bed and pullout sofa. Microwave, coffee maker, stove top, refrigerator/freezer, 62" Smart TV, gas BBQ. Hot tub (only available from Oct 1st-May 31st) Enjoy the sun, beautiful nature of Anclote River with 3 kayaks and 3 paddle boards. Daily sightings of dolphins, manatees and many species of birds passing by. Fish right off the sea wall. Beach is a short 2-miles away. Overnight boat docking.

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

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

Warmth In Holiday
Tiny Living In Holiday offers a delightful and peaceful ambiance, ideal for a serene getaway. Conveniently located near stunning beaches, guests can revel in the beauty of the coast. The room creates a warm and homely atmosphere, ensuring guests feel snug and content during their stay. Furthermore, the room features a handy air fryer microwave oven combo, allowing guests to effortlessly prepare meals at their convenience. Listing does not accommodate infants/toddlers.

Private Studio with Lake Access Near Beaches
Your perfect stay near the water. Private studio for 2, ideal to relax, work comfortably, and enjoy a peaceful lake view just a few steps away through a short hallway. Enjoy self check-in 24/7, private parking, a queen bed, fast WiFi, a workspace, and a fully equipped kitchen. Near Tarpon Springs and beaches like Fred Howard and Sunset Beach, with easy access to Dunedin, Clearwater, New Port Richey, and Tampa. ✨ Promotions may apply. Save or book today.

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.

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.

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!

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.

Family Coastal Home w/ EV Charger, Bikes &Kayaks
🌴 Enjoy a spacious home perfect for adventure and relaxation! Charge your EV, fire up the BBQ, and make use of the fenced yard with plenty of space for your boat or water toys. Just minutes from historic Tarpon Springs, scenic parks, and beautiful beaches, this home is ideal for hiking, biking, fishing, and kayaking adventures 🛶. Relax in comfort after a day full of fun!
Popular amenities for Holiday vacation rentals
Other great vacation rentals in Holiday

Tarpon Family Retreat-Heated Pool, Fire Pit & Fun!

Lazy Day Oasis

Gulf Access, Heated Pool, Near Islands, Beaches

Endless Summer

Modern Serene Escape: Near Tarpon Springs Beaches

Brisas del Mar

Deluxe 3bd/2ba w/Heated Pool

Coastal Gem • WFH • Walk to Park, Trails & Water
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R1,949 ZAR | R2,150 ZAR | R2,100 ZAR | R2,100 ZAR | R1,932 ZAR | R1,982 ZAR | R1,932 ZAR | R1,848 ZAR | R1,814 ZAR | R1,713 ZAR | R1,865 ZAR | R1,965 ZAR |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Frequently Asked Questions
Are there family-friendly vacation rentals in Holiday?
Holiday has more than 100 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Holiday?
Experience the best of Holiday with our house rentals, starting at about $20 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there pet-friendly vacation rentals in Holiday?
Four-legged friends are welcome in Holiday. Choose from more than 80 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Holiday?
Yes! Work meets play with ease at over 70 vacation rentals in Holiday featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Holiday vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Holiday, available on Airbnb. Make a splash and soak up the sun in style!
Where should I stay in Holiday?
Make yourself at home in Holiday by choosing from our most frequently booked neighborhoods. We have over 950 vacation rentals in Orangewood Village, over 540 vacation rentals in Forest Hills, and over 450 vacation rentals in Buena Vista.
Do house rentals in Holiday have air conditioning?
Absolutely! We offer over 120 house rentals with air conditioning in Holiday. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Holiday have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Holiday. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Holiday have wifi?
Absolutely! We offer over 120 house rentals with wifi in Holiday. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Holiday have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Holiday. Enjoy a tailored experience with all the comforts you desire.
All about Holiday
Located just outside of Tampa Bay, Holiday combines the convenience of suburban living with easy access to Central Florida’s most popular natural attractions. The town’s Main Street offers everything from craft breweries to farmer’s markets, as well as an array of locally-owned shops and restaurants. Just west of downtown, you can find Key Vista Nature Park, a sprawling oceanfront park that has its own boardwalk and dog park, and is quite popular for hiking, fishing, and wildlife spotting. From Holiday, it is just a 30-minute drive to Honeymoon Island State Park and its four miles of white sand beaches leading to the Gulf of Mexico.
The three-mile Osprey Trail runs through a virgin slash pine forest, where you can spot eagles, great horned owls, and osprey circling overhead. Clearwater Beach, known as one of Florida’s best beaches, is only 20 minutes away, while the nearby city of St. Petersburg has a collection of world-class museums, such as The Dalà (Salvador Dalà Museum), the Florida Holocaust Museum, and the Chihuly Collection, which showcases glass sculptures.
What are the top things to do in Holiday?
Key Vista Nature Park
Located just west of Holiday, the Key Vista Nature Park stretches out for more than 100 acres along the ocean and allows you to immerse in the beautiful natural surroundings without leaving the suburbs. The park features a lovely boardwalk through the forest, an observation tower looking over the Gulf of Mexico, and well-maintained hiking trails where you may see squirrels, peacocks, snakes, and an abundance of birds.
Whimzeyland
Part family home, part art installation, Whimzeyland provides a major splash of color to the nearby suburb of Safety Harbor. This rainbow-colored house started just like any other house in the neighborhood, but the owners have added works of art to the interior and exterior over the past few decades. You will find a psychedelic garden, a gallery of bowling balls, an enormous moon statue, and decorated cars. The house is accessible on guided tours and offers some fantastic photo opportunities.
Historic Sponge Docks
In the early 20th century, many newly arrived immigrants from Greece settled in Tarpon Springs to work in the local sponge industry. This fascinating waterfront area brings the region’s Greek culture to life with scores of authentic Greek restaurants and historic sailboats that wouldn’t look out of place in the Aegean Sea. The sponge docks are just a 10-minute drive from Holiday.
Quick stats about vacation rentals in Holiday

Total vacation rentals
Explore 150 vacation rentals in Holiday

Nightly prices starting at
Holiday vacation rentals start at R336Â ZAR per night before taxes and fees

Verified guest reviews
Over 3,970 verified reviews to help you choose

Family-friendly vacation rentals
100 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 80 rentals that welcome pets

Vacation rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wi-Fi availability
150 of Holiday vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Holiday rentals

4.7 Average rating
Holiday stays receive an average rating of 4.7 out of 5 from guests
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- Rentals with a patio Holiday
- Rentals with a fireplace Holiday
- Family-friendly rentals Holiday
- Rentals with a fire pit Holiday
- Waterfront rentals Holiday
- Pet-friendly rentals Holiday
- Rentals with lake access Holiday
- Rentals with pools Holiday
- Rentals with outdoor seating Holiday
- Rentals with a washer and dryer Holiday
- Rentals with beach access Holiday
- House rentals Holiday
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