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Vacation rentals in Holiday

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Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Holiday vacation rentals

Self check-in
Monthly stays
Gym
BBQ grill
Laptop-friendly workspace

Stay near Holiday's top sights

Miss Vicki's On The River37 locals recommend
La Fondita de Leo10 locals recommend
Publix Super Market at Holiday Centre8 locals recommend
PK's PlayZone & Grille4 locals recommend
Dunkin'3 locals recommend
ALDI3 locals recommend

Other great vacation rentals in Holiday

Top guest favorite
The exterior of the home features a spacious driveway leading to a two-story structure with a charming balcony. Lush greenery and manicured landscaping enhance the inviting curb appeal, complemented by soft sunset colors illuminating the sky.
Home in Palma Ceia
4.97 out of 5 average rating, 31 reviews

SouthTampa-Family&Group Oasis-3K bd, private pool

Guest favorite
The entrance features a bright pink exterior, complemented by white trim and a welcoming white door labeled 'B.' Lush green plants are arranged on either side of the door, enhancing the cheerful appeal. A well-maintained artificial lawn lies in front, with a simple concrete pathway.
Cottage in Indian Rocks Beach
4.9 out of 5 average rating, 287 reviews

Vintage Florida Beach Cottage B

Guest favorite
Apartment in Indian Rocks Beach
4.8 out of 5 average rating, 274 reviews

Enjoy brand new vacation 2/2 condo & water park!

Superhost
A modern kitchen features white cabinetry with sleek handles and a spacious countertop. Stainless steel appliances, including double ovens and a cooktop, are integrated into the design. Under-cabinet lighting adds a bright ambiance, highlighting the elegant marble backsplash.
Home in Holiday
4.77 out of 5 average rating, 31 reviews

Luxurious holiday home

Guest favorite
A spacious living room is displayed, featuring elegant furniture arrangements on glossy tile floors. Natural light brightens the area through large windows. A staircase can be seen in the background, leading to an upper level, while a dining area is visible in the adjacent space.
Home in Tampa
4.9 out of 5 average rating, 10 reviews

Bring your family and friends to our luxury airbnb

Top guest favorite
A well-maintained staircase with beige carpeting is pictured, featuring white wooden railings and spindles. The walls are painted in a neutral tone, and a small wall-mounted shelf is visible beside the stairs, enhancing the clean design.
Condo in Redington Beach
4.91 out of 5 average rating, 173 reviews

2min walk to the beach/pool, BBQ/great area, RO110

Guest favorite
Home in Tampa
4.9 out of 5 average rating, 105 reviews

Luxury Home centrally located in Tampa Bay!

Superhost
The pool area features a curved swimming pool surrounded by vibrant greenery and palm trees. Several lounge chairs are arranged on the side. The area is enclosed by a white fence, providing a sense of privacy.
Apartment in Largo
4.78 out of 5 average rating, 281 reviews

Mini-Golf 2/1 with Heated pool.

Show all

Quick stats about vacation rentals in Holiday

  • Total rentals

    120 properties

  • Nightly prices starting at

    ﺩ.ﺇ73 before taxes and fees

  • Total number of reviews

    3.3K reviews

  • Family-friendly rentals

    80 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 420 vacation rentals in Buena Vista Melody Manor, over 420 vacation rentals in Buena Vista, and over 830 vacation rentals in Orangewood Village.

  • Are there vacation rentals with a dedicated workspace in Holiday?

    Yes! Work meets play with ease at over 60 vacation rentals in Holiday featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • 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 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!

  • 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.

  • 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, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

Destinations to explore

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