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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.

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Top guest favorite
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
4.94 out of 5 average rating, 181 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!

Top guest favorite
A vintage windmill stands gracefully among lush trees, surrounded by fallen leaves. In the foreground, a cozy bed is visible, adorned with green accents and soft bedding, conveying a serene atmosphere. Natural light filters through the foliage, enhancing the tranquil setting.
Apartment in Timber Oaks
5 out of 5 average rating, 199 reviews

The Bohemian Studio Countryside Gem Separate Entry

THE BEST OF BOTH WORLDS NO EXTRA FEES. Cozy Studio in a private countryside place but just minutes away from hospitals, restaurants, shopping, springs, beach & downtown. Self-check-in & separate entry. Enjoy your private fenced patio, full bathroom & fully equipped kitchen. Located on 2 acres w/ plenty FREE parking, high-speed internet, ethernet & FREE Netflix. This is the perfect spot for business, family trips, traveling nurses, romantic escape for couples & nature lovers at an excellent price

Top guest favorite
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.
Cottage in Tarpon Springs
4.98 out of 5 average rating, 120 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!

Top guest favorite
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.
Vacation home in Tarpon Springs
4.98 out of 5 average rating, 113 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.

Top guest favorite
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.
Apartment in New Port Richey
5 out of 5 average rating, 106 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!

Guest favorite
The bedroom features a spacious bed dressed in a floral-patterned coverlet. A small table is placed at the foot of the bed, displaying the word 'RELAX.' A closet is visible beside the bed, and light-colored walls complement the wooden flooring.
Guest suite in Holiday
4.97 out of 5 average rating, 63 reviews

Cozy&Private|Big Parking|Near Beach

Cozy and private apartment with no cleaning fee, spacious parking, and just minutes from the beach and Little Greece. Located in a quiet and safe area, it’s ideal for relaxing or working from home. Enjoy : ✔ Fully equipped kitchen ✔ Bedroom with work desk ✔ Smart TV, WiFi ✔ Spacious bathroom with high-capacity shower ✔ Free parking Ideal for couples or solo travelers seeking peace near the sea.

Top guest favorite
An outdoor seating area is situated on a lawn, featuring a small black table and two chairs. The view includes the serene Pithlachascotee River, along with a dock and decorative features, framed by lush trees and greenery.
Guesthouse in New Port Richey
5 out of 5 average rating, 185 reviews

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.

Guest favorite
Home in Forest Hills
4.91 out of 5 average rating, 117 reviews

Pool Getaway · Near Tarpon Springs & Beaches. 5 mi

Private pool oasis near Tarpon Springs, Dunedin, Clearwater & Tampa. Built for families/friends: fast Wi-Fi, workspace, equipped kitchen, BBQ patio and chill areas. Self check-in 24/7 and free parking. Close to beaches and nature parks for walks and exploring. Quiet for sleep; practical for work. Last-minute deals live this week. Book today and enjoy your own pool.

Guest favorite
A welcoming entryway features a sliding barn door that leads to a cozy sleeping area. A small table with four black chairs is positioned against the wall. Soft lighting illuminates the space, while decorative elements, including artwork and plants, add charm.
Apartment in Holiday
4.99 out of 5 average rating, 67 reviews

Cozy apartment private retreat

Welcome to Your Cozy Retreat! Escape to our charming guest house. This beautifully decorated space offers a perfect blend of comfort and style, making it an ideal getaway for couples, solo adventurers, and business travelers alike. Amenities: Free Wi-Fi Air conditioning and heating Complimentary coffee. Towels and chairs Free parking on premises. Security Cameras

Guest favorite
Home in Tarpon Springs
4.78 out of 5 average rating, 157 reviews

Mins to Beach/Studio Home/walk to dwtn/FreeParking

✨ Beautifully remodeled studio in the heart of Tarpon Springs. Just an 8-minute drive to the beach, this cozy retreat was thoughtfully designed with comfort in mind. Featuring a comfy queen bed and a bright, welcoming interior, it’s the perfect spot to relax after exploring the Sponge Docks, downtown, and nearby attractions.

Top guest favorite
A cozy sleeping area is presented with a spacious bed covered in golf-themed bedding. A light-colored accent wall complements the wood-like flooring. Natural light enters through a window featuring blinds. Additional decor includes subtle golf-themed artwork and a closet unit in the corner.
Tiny home in Port Richey
4.97 out of 5 average rating, 136 reviews

Golf-Themed Tiny Home w/ Private Entrance & Patio

Welcome to The 19th Hole Suite! Escape to your own cozy retreat at The 19th Hole, a fully detached tiny home designed for total privacy and relaxation. Whether you’re traveling for work, passing through, or planning a peaceful getaway, you’ll love the comfort, quiet, and fun touches we’ve added just for you.

Guest favorite
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.
Place to stay in New Port Richey
4.94 out of 5 average rating, 173 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

Quick stats about vacation rentals in Holiday

  • Total rentals

    120 properties

  • Nightly prices starting at

    ﺩ.ﺇ37 before taxes and fees

  • Total number of reviews

    3.9K reviews

  • Family-friendly rentals

    90 properties are a good fit for families

  • Pet-friendly rentals

    60 properties allow pets

  • Rentals with a pool

    30 properties have a pool

Your guide to Holiday

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 Dalí (Salvador Dalí Museum), the Florida Holocaust Museum, and the Chihuly Collection, which showcases glass sculptures.


The best time to stay in a vacation rental in Holiday

There is no bad time to rent cabins in Holiday. Thanks to the warm weather, Tampa Bay is a popular summer destination, making local attractions more busy than usual during this season. Things are much quieter during the spring and fall, so you may find fewer people in the Key Vista Nature Park and Honeymoon Island State Park. Winter starts to pick back up again as people head to Florida to get a bit of sunshine.

The Tampa Bay/Clearwater area hosts many interesting events throughout the year, including a jazz festival in October, when the city’s waterfront becomes a venue for musicians from around the world. The Mainsail Arts Festival in April is a free open-air event with live music and a food court in addition to local works of art.


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.

Frequently Asked Questions

  • Where should I stay in Holiday?

    Make yourself at home in Holiday by choosing from our most frequently booked neighborhoods. We have over 410 vacation rentals in Buena Vista Melody Manor, over 870 vacation rentals in Orangewood Village, and over 410 vacation rentals in Buena Vista.

  • 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 pet-friendly vacation rentals in Holiday?

    Four-legged friends are welcome in Holiday. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there Holiday vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Holiday, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in apartment rentals in Holiday?

    Experience the best of Holiday with our apartment rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Holiday have self check-in?

    Absolutely! We offer over 10 house rentals with self check-in 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 house rentals in Holiday have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Holiday. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Holiday?

    Holiday has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • What are the most popular amenities for House Rentals in Holiday?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a bbq area, over 10 homes with self check-in, over 100 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

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