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, 182 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!

5 out of 5 average rating, 155 reviews

The image showcases a tranquil bedroom area with a queen-sized bed adorned with botanical-themed bedding. A sofa is positioned beside the bed, complemented by wall art featuring greenery. The backdrop features a serene outdoors view of trees and grassy space, creating a sense of privacy.

Apartment in Timber Oaks

Jungle Studio. Private with Separate Entry & Patio

PRIVACY & COMFORT AT THE BEST PRICE. Country setting near everything. Experience affordability & convenience with NO extra fees! Enjoy peace and quietness at this spacious retreat. Separate entry & FREE parking. Just 10 mins to hospitals, near highways, restaurants & shops Features a queen bed, 45" TV with FREE Netflix, full kitchen, dinning area & full bathroom, high-speed internet & private, fenced patio. Perfect x travel nurses, business trips, golfers, romantic getaways & "snowbird" guests.

Vacation home in Tarpon Springs

A cozy living room is displayed with a green sofa positioned beside a plant. A coffee table sits at the center, accompanied by a light fixture and a wall art piece. Natural light filters through the window, illuminating the warm wood flooring.

4.97 out of 5 average rating, 116 reviews

Modern Home Great Location

Welcome to your home away from home. Our guests’ comfort is our priority. Equipped with all your creature comforts and surrounded by modern fixtures and decor to ensure a wonderful vacation. Open Floor plan, huge kitchen, and two cozy bedrooms. Walking distance to all the local restaurants and attractions, without the noise to keep you up at night; you couldn't choose a better location Please note: this is a duplex property, so you'll be sharing the building but enjoying your own private space.

Superhost

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.

Guesthouse in Tarpon Springs

4.85 out of 5 average rating, 102 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

4.99 out of 5 average rating, 145 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

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.

4.97 out of 5 average rating, 88 reviews

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

4.99 out of 5 average rating, 258 reviews

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

Heated & Screened in Pool-All Essentials Provided

🏡 Private Pool House with Large Covered & Screened-In Porch Relax and unwind in this inviting private pool home, featuring a large covered and screened-in porch—perfect for enjoying the outdoors without the bugs. 🌊 Heated Pool Take a dip in the private pool, heated year-round with an electric heat pump (weather permitting), offering comfort no matter the season. Whether you're sipping coffee on the porch or enjoying a swim, this cozy retreat is ideal for a peaceful and private getaway.

4.94 out of 5 average rating, 110 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.

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, 83 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

Apartment in New Port Richey

A spacious sleeping area features a large bed with a neatly arranged white coverlet. A comfortable sitting area is visible on the side, complemented by a lamp that provides soft lighting. A small window with light-colored curtains adds natural brightness to the room.

5 out of 5 average rating, 108 reviews

Cozy Apt. Suite - Sunny Tampa Bay Area

Don’t be fooled,This is a real gem and remodeled unit. Kick back and relax at this peaceful and cozy suite. Located near Historic Downtown New Port Richey and Trinity Area. You can visit the nearby Tarpon Springs Sponge Docks, Honeymoon Island or Clearwater which is rated one of the top 10 beaches in the nation. We are centrally located near 3 community hospitals. Travel Nurses or Professionals are welcomed. Whether you are traveling for leisure or work this is the place for you!

A screened-in lanai offers a comfortable seating area with a wicker couch and coffee table overlooking a swimming pool. The space is adorned with potted plants and hanging light fixtures. A dog sits by the couch. The backdrop features a private yard, enhancing the outdoor atmosphere.

4.92 out of 5 average rating, 24 reviews

Heated Pool, Hot Tub & Sand Volleyball

Your perfect getaway awaits in this pet-friendly 2BR/2BA retreat! Relax by the in-ground pool and hot tub, play a game of sand volleyball, unwind on the deck or have a BBQ. The fully fenced yard offers privacy, while the covered outdoor seating, pool-side hammock, fire pit, and a variety of games make it fun for all. With WiFi, AC, and a workspace, it’s perfect for both short and long stays. Just minutes from the beach, dining, and entertainment.

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.

4.91 out of 5 average rating, 121 reviews

5 mi to Tarpon & Beaches• House with Heated Pool

Oasis with a private pool heated Nov–Mar and a patio, 5 miles from Tarpon Springs, near Dunedin and a short drive to Clearwater/Tampa. Perfect for family or friends: fast Wi-Fi, workspace, fully equipped kitchen, and BBQ. 24/7 self check-in and on-site parking. Quiet for restful nights; beaches and parks minutes away. Note: pool heating available November–March (weather-dependent). Last-minute promos active. Book today!

Popular amenities for Holiday vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Stay near Holiday's top sights

Anclote River Park

86 locals recommend

Tarpon Springs Aquarium And Animal Sanctuary

103 locals recommend

Key Vista Nature Park

31 locals recommend

Other great vacation rentals in Holiday

A serene view from the screened lanai highlights a private heated pool, reflecting the soft colors of a sunset. The tranquil waters of the Anclote River can be seen beyond the pool, framed by lush greenery and trees along the riverbank.

4.98 out of 5 average rating, 46 reviews

River Home with Pool, Sunset, Dolphin & Fishing

A living area features a dark gray sectional sofa adorned with blue and white decorative pillows. A glass coffee table sits in the center, complemented by a flat-screen TV and a light fixture. Natural light enters through blinds on the windows, enhancing the spacious feel.

5 out of 5 average rating, 8 reviews

Florida Stay & Play Getaway Home

A clear glass fish-shaped container holds a variety of seashells, showcasing a coastal theme. The warm wooden surface beneath complements the decor, with a blurred background revealing a cozy living area adorned with soft furnishings and light-colored textiles.

4.88 out of 5 average rating, 68 reviews

Finca Vigia

4.97 out of 5 average rating, 31 reviews

A bright, well-lit room features a spacious bed covered with a dark quilt and neatly arranged white towels. A piece of art hangs above a nightstand, complementing the light-colored walls and wooden flooring. Soft lighting is provided by recessed ceiling fixtures.

Place to stay in Holiday

Cozy place! Pet are welcome!

A light-filled living area features a spacious sectional sofa and a wooden table with a decorative chair. Natural light streams in through large windows with shades, illuminating the neutral color palette and coastal-inspired decor, creating a relaxed environment.

4.97 out of 5 average rating, 66 reviews

*NEW* Riverside Retreat w/Pool

The bedroom features a spacious bed adorned with a textured white coverlet and colorful decorative pillows. Two bedside tables with lamps flank the bed, while beach-themed artwork and signs are mounted on the walls. A comfortable armchair is positioned near the entrance, enhancing the cozy ambiance.

4.92 out of 5 average rating, 99 reviews

The Sunset Suite

4.82 out of 5 average rating, 93 reviews

A spacious bed is dressed in soothing blue bedding, complemented by matching pillows. Light curtains frame the window, while an accent lamp and a small table sit beside the bed. A decorative mirror and a plant add a touch of elegance to the room.

Guest suite in Holiday

Buena Vista

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.