Pet-friendly holiday rentals in Holiday

Simply Charming

Summertime is here! Perfect place to stay. Relax with the entire family at this peaceful place. It is also perfect for a romantic getaway or a family vacation. It has a screened in back porch. It also has a washer and dryer. Central A/C and heating. It has a workspace, & 2 large screen TVs. It's pet friendly. Completely fenced in backyard. Centrally located. Easy access to Tampa, Dunedin, Clearwater, and St. Petersburg. Easy access to beaches. Book now and hit the beach! Visit "Greek Town" too!

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

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.

The Cozy Spot !

“Our space is designed to make you feel at home from the very first moment.What makes this place special is its perfect mix of comfort, style, and location.A cozy and modern atmosphere, ideal for both relaxing and working. Comfortable beds and well-organized spaces, created with your comfort in mind. Outdoor area perfect for enjoying your morning coffee or a glass of wine at sunset Great location/ shopping centers / restaurants / local attractions] yet quiet enough for peaceful rest.

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!

Lakefront Bungalow |Fenced Yard | 10 Min to Tarpon

Blue Shore Bungalow – Lakefront Getaway Near Tarpon Springs Welcome to The Blue Shore Bungalow — a charming 2-bedroom, 1.5-bath lakefront retreat fully fenced that sleeps 6. Relax with peaceful water views, coastal-inspired interiors, and a cozy outdoor space perfect for morning coffee or sunset lounging. Just minutes from Tarpon Springs, Dunedin, local beaches, restaurants, and shops. Ideal for couples, families, or friends looking for a quiet getaway close to everything.

Beachy Holiday Hideaway- 3/2 up to 6 guests

Bring the whole family to this great Florida style home. Centrally located in Holiday, close to beaches, parks & world famous Sponge Docks. Anclote Gulf Park- 6 miles Key Vista Nature Park- 5 miles Tarpon Springs Sponge Docks- 4 miles Anclote Beach- 5 miles Fred Howard Park- 7 miles Innisbrook Golf Resort & Spa- 8 miles Honeymoon Island State Park- 15 miles Clearwater Beach- 23 miles Tampa International Airport- 28 miles Busch Gardens- 31 miles Disney World- 94 miles

Walk to Downtown•King Bed • Outdoor Lounge•Coastal

✨ Relax in your outdoor lounge, enjoy a game night under the lights, and walk to downtown for drinks and dining — all just minutes from the beach. This fully remodeled 1-bedroom with king bed is designed for a simple, comfortable stay with everything you need to unwind. Enjoy access to a spacious shared outdoor lounge area — perfect for relaxing or a casual game night. This is a single-story property. Highly rated by guests for location, cleanliness, and comfort.

*NEW* Riverside Retreat w/Pool

Take it easy at this unique and tranquil getaway. Welcome to our Riverside Retreat where you will enjoy incredibly relaxing peaceful days, and sunset views. Recently renovated 2 Bedroom, 2 Full Bathroom, pool home with dock and privacy fenced backyard on the Anclote River. This home is fully equipped and is ready for you to enjoy. Conveniently located and only a 9-minute drive to the World-famous Sponge Docks and minutes from our award winning beaches…

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.

Private pool home near Tarpon Springs 5 mi

🌴 Private pool home near Tarpon Springs, Gulf beaches, restaurants, and local attractions—perfect for a relaxing Florida getaway. Enjoy a fenced patio, BBQ area, fast WiFi, workspace, fully equipped kitchen, 24/7 self check-in, and on-site parking. Easy access to Dunedin, Clearwater, Tampa, and nearby beaches. ✨ Note: pool heat is available Nov–Mar, weather permitting. ⏳ Last-minute promos active—book and lock in your dates!

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!