
Holiday rentals in Holiday
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Top-rated holiday 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

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

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 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

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!
Popular amenities for Holiday holiday rentals
Other great holiday rentals in Holiday

Canal‑Front Oasis w/Heated Pool Close to the Beach

Home with access to the Gulf.

Brisas del Mar

Modern Retreat, 9 Mins to Beach, Fast Wi-Fi

Deluxe 3bd/2ba w/Heated Pool

Waterfront Retreat W / Floating Dock & Kayaks

Anclote River House #3

Coastal Farmhouse 2bd, fenced yard, pets welcome!
When is the best time to visit Holiday?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £93 | £91 | £92 | £92 | £85 | £87 | £85 | £81 | £80 | £75 | £82 | £86 |
| 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 apartment rentals in Holiday have wifi?
Absolutely! We offer over 10 apartment 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.
Quick stats about holiday rentals in Holiday

Total holiday rentals
Explore 150 holiday rentals in Holiday

Nightly prices starting at
Holiday holiday rentals start at £15 per night before taxes and fees

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

Family-friendly holiday rentals
100 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 80 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
70 properties have a dedicated workspace

Wifi availability
150 of Holiday holiday rentals include wifi 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 lake access Holiday
- Family-friendly rentals Holiday
- Rentals with beach access Holiday
- Rentals with outdoor seating Holiday
- Rentals with a washing machine and dryer Holiday
- Rentals with a fireplace Holiday
- House rentals Holiday
- Rentals with a firepit Holiday
- Rentals with pools Holiday
- Waterfront rentals Holiday
- Pet-friendly rentals Holiday
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Anna Maria Island Beach
- Bean Point Beach
- Weeki Wachee Springs
- Vinoy Park
- Amalie Arena
- Dunedin Beach
- Tampa Convention Center
- Sand Key Beach
- St Pete Beach
- Hard Rock Casino
- Jannus Live
- Anna Maria Public Beach
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Fort Island Beach
- North Beach At Fort DeSoto Park
- Tropicana Field
- University of South Florida
- Splash Harbour Water Park





