Vacation rentals in Holiday

4.95 out of 5 average rating, 188 reviews

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.

Home in Holiday

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!

Cottage in Tarpon Springs

The exterior of the cabin is showcased, featuring a white façade and a welcoming front porch. Decorated with colorful plants, the walkway leads to the entrance, framed by lush greenery and tall trees providing natural shade.

4.98 out of 5 average rating, 123 reviews

Cooper Cabin: Cute, Adorable, Standalone Studio

Cooper Cabin is a super cute and sparkling clean stand alone studio with a full eat-in kitchen and bath. 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! Located within walking distance of all things Tarpon Springs and just a short 7 min drive to Fred Howard Beach, Cooper Cabin is decorated with fun decor and a relaxing front porch balcony with bistro set. Bikes and beach gear provided!

4.79 out of 5 average rating, 121 reviews

A private solar-heated pool is surrounded by lush greenery, creating a serene outdoor space. Two lounge chairs are positioned poolside, with a small table nearby, inviting relaxation in a peaceful atmosphere.

Home in New Port Richey

Pool Paradise - Private Solar Heated Pool

Welcome to your private vacation gateway. Escape to Florida Sunshine Sanctuary in Tampa Bay Area. Our 2 Bedroom/ 2 Bathroom House is nested in a quiet suburb not far from the Tampa Airport. It is 25 miles from the famous Clearwater Beach and 30 miles from the Busch Gardens. Take the ultimate one day trip to DisneyWorld which is a 2 hour drive form the house. Also a 15 min drive to Greektown and Tarpon Springs Sponge Deck. House is nicely decorated with everything needed to create special memorie

Guesthouse in Tarpon Springs

A comfortable living space includes a dark blue sofa with accent pillows and a coffee table. A dining area with wooden chairs is visible in the background, alongside a fully equipped kitchen. Light-colored cabinets and appliances complement the space.

4.87 out of 5 average rating, 115 reviews

Comfy 1BR Near Beaches & Sponge Docks

Enter your private oasis & enjoy our spacious 1 bd in scenic Tarpon Springs. Relax on the comfy couch or oversized chair. Treat yourself to free snacks, cold water & coffee, tea or hot cocoa w/ the Keurig in the fully equipped kitchen! Enjoy a hot shower or bath. Extra toiletries supplied. Games & books available. Comfortable Queen size bed ensures a great sleep. Only 3 miles from Howard Park Beach & Sponge Docks. Sunset Beach 1.3 miles. Innisbrook Golf Resort 3.9 miles! Private Entrance

4.94 out of 5 average rating, 117 reviews

Two black rocking chairs with Buccaneers branding are positioned on a light-colored deck. Lush green grass and palm trees frame the view, with a path leading to a screened-in patio visible in the background under a bright blue sky.

Home in Port Richey

Gulf Harbors Vacation Oasis

This lovely Gulf Harbors home with open floor plan & in-ground heated pool is the perfect getaway! Home on canal that leads directly to the Gulf in minutes-amazing view & quiet, safe neighborhood! Perfect home base for shopping, restaurants, kayaking, exploring, & especially Scalloping in Pasco county! This region includes all state waters south of the Hernando – Pasco county line & north of the Anclote Key Lighthouse in northern Pinellas County,& includes all waters of the Anclote River.

4.99 out of 5 average rating, 86 reviews

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.

Home in Holiday

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

4.91 out of 5 average rating, 130 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

Heated Pool • Near Tarpon & Gulf 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!

4.96 out of 5 average rating, 375 reviews

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

This home is ideally located near Florida's beautiful Sunset Beach and Howard Park Beach - only 17 miles from Clearwater Beach. Take a short ride to world famous attractions like Disney, or Busch Gardens. Don't settle for a hotel when you and your guests can enjoy a home with a gas grill, multiple patios, large kitchen/family room, a large 4K TV and a private jacuzzi/pool with gas heater *option. It's a perfect place for creating family memories or getting together with old friends.

4.71 out of 5 average rating, 110 reviews

A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.

Home in Oldsmar

Private Pool Home Near Clearwater & Tampa

Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

4.97 out of 5 average rating, 140 reviews

A spacious living area features a comfortable beige couch and a plush armchair. Natural light fills the space through large glass sliding doors leading to a balcony overlooking greenery. A wall-mounted TV and a small dining table with stools are also present, enhancing the welcoming environment.

Condo in Palm Harbor

Newly Remodeled Condo In The Heart Of Innisbrook

Newly remodeled, fully furnished second floor, one bedroom condo with 1 King bed and 1 Queen sofa. The condo has a fully equipped kitchen for your convenience and comfort. You will have access to the ("no fee")laundry room and hotel Ice maker on the same floor. Free parking is conveniently outside your building door.

Bungalow in New Port Richey

A calm waterfront scene showcases a tree with sprawling branches above the water. A blue bridge can be seen in the distance, alongside boats docked along the serene riverbank. Reflections of the surrounding greenery and buildings are visible on the water's surface.

4.94 out of 5 average rating, 114 reviews

1928 Riverfront Bungalow with boat dock

Waterfront ranch Bungalow. Quaint with FP, orig refin hardwood floors, New kitchen with SS appliances, granite countertops, 2 master suites, one with river views. Screened in front porch, garage & floating dock. Washer & dryer. Completely furnished with antiques. Walking path along the river. Step back in time.

Place to stay in New Port Richey

A spacious sleeping area is highlighted by a wooden bed frame adorned with a light-colored quilt featuring floral patterns. A small writing desk and chair are positioned near the window, while a sliding wooden door leads to an en-suite bathroom.

4.92 out of 5 average rating, 198 reviews

Sunflower Studio

Here you wake up to birdsong, as we are in the middle of a bird sanctuary. A peaceful place in the middle of a busy city. Sunflower Studio is a unique experience that you must feel. It will be a pleasure to welcome you, make your reservation!

Popular amenities for Holiday vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Holiday's top sights

Anclote River Park

89 locals recommend

Tarpon Springs Aquarium And Animal Sanctuary

108 locals recommend

Key Vista Nature Park

33 locals recommend

Other great vacation rentals in Holiday

5 out of 5 average rating, 27 reviews

Tiny home in Holiday

Modern style tiny house

5 out of 5 average rating, 7 reviews

A modern single-story home is depicted, featuring a clean exterior with a gray facade and a spacious driveway. A two-car garage is visible, and the front yard is landscaped with greenery. Clear blue skies are present in the background.

Home in Port Richey

Cozy home! Pool.

4.98 out of 5 average rating, 53 reviews

Home in Forest Hills

River Home with Pool, Sunset, Dolphin & Fishing

4.85 out of 5 average rating, 54 reviews

A spacious living area features a large sectional sofa paired with wooden side tables. A table with a decorative plant and a vase is centered. The wall art depicts palm trees against a sunset backdrop. Bright natural light fills the room through large windows with sheer curtains.

Home in Port Richey

Sunrise 2

4.98 out of 5 average rating, 41 reviews

The compact kitchen features a microwave, refrigerator, and a sink with a cutting board. Green accents adorn the curtains, complementing the organized space. A small dining area with a colorful tablecloth is positioned nearby, providing a cozy spot for meals. Thoughtful organization ensures convenience.

Camper/RV in Timber Oaks

Private RV Retreat & Outdoor Oasis. Deal Jan-May

4.83 out of 5 average rating, 30 reviews

The exterior of the property is shown, featuring a light-colored house with a welcoming entrance. A paved driveway leads to a garage, surrounded by neatly arranged white stones and potted plants. The sky is mostly clear with scattered clouds.

Home in Holiday

The Melody Hideaway

4.81 out of 5 average rating, 16 reviews

Apartment in Holiday

The Cozy Spot !