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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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Guest favorite
The charming exterior of the home is showcased at dusk, with warm lighting illuminating the entrance and garden. The driveway leads to a single-car garage, while solar-powered lights line the path, enhancing the inviting appearance of this mid-century oasis.
Home in Holiday
4.95 out of 5 average rating, 217 reviews

King Bed Ensuite+Queen 2/2/1—2 Living Spaces+4TVs

Step through the cheery door into your 2BD/2BA mid-century oasis. This home provides an elegant, yet comfortable vibe while featuring lavish amenities including 4 Smart TVs, a fully equipped kitchen, 2 living spaces, a dedicated workspace, a master ensuite, luxury mattresses, private patio, garage parking, a washer & dryer. Enjoy all the comforts while being minutes to grocery stores, restaurants, Tarpon Springs/Sponge Docks(4.9mi) Anclote Beach(4.8mi) Honeymoon Island State Park(16.2mi) & more!

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
4.97 out of 5 average rating, 124 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
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
5 out of 5 average rating, 168 reviews

Jungle Studio. Private with Separate Entry & Patio

NEW YEAR SPECIAL: TOP PRIVACY & BEST VALUE in the Area. Great location, countryside escape near everything. Experience affordability, convenience, peace and quietness at this spacious retreat. Separate entry & 2 FREE parkings. Just 10 mins to hospitals, highways, restaurants & shops. Features a queen bed, 45" TV with FREE Netflix, full kitchen, dinning area, a full bathroom, high-speed internet and a private, fenced patio. Perfect x travel nurses, business trips, golfers, couples & "snowbirds"

Superhost
A modern bathroom is shown featuring a sleek vanity with a rectangular sink and black fixtures. A round mirror is illuminated by three overhead lights. Storage is provided by wooden drawers beneath the sink, and towels are neatly arranged on shelves.
Guesthouse in Palm Harbor
4.87 out of 5 average rating, 165 reviews

Home away from home

Private unit has designated parking, pool access, its own water heater, water softener, filtration system, 2 ceiling fans, heater, air purifier & a/c. Featuring a queen bed, dresser, 42” tv & fire stick w/ streaming accounts, wifi, full length mirror, recliner, eating table & chairs. The bathroom has a walk-in shower, large vanity mirror, & all the needed bathroom accessories. Full kitchenette w/ microwave, dual burner, air fryer, tea kettle, coffee maker, & more. Owner lives on property.

Top guest favorite
The exterior of a newly constructed barn loft apartment is shown, featuring a wraparound deck accessed by wooden stairs. Beneath the deck, picnic tables and seating areas are visible among the surrounding greenery and trees. The property is set in a spacious outdoor environment.
Barn in Odessa
4.98 out of 5 average rating, 125 reviews

Cypress Lakes Barn Retreat

Rest & relax at this newly constructed barn loft apartment, located on a 4 acre hobby farm in Odessa, Florida on a private lake. This one bedroom, one bath and kitchen is clean, fun, and convenient. We have 2 daily feedings of farm animals at which you can participate including horses, cows, goats, & chickens; or you can choose to kayak on the lake. This memorable place is anything but ordinary, and is conveniently located 11 miles from the airport and is a quick drive to dining & shopping.

Top guest favorite
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
4.99 out of 5 average rating, 261 reviews

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.

Guest favorite
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.
Home in Holiday
4.92 out of 5 average rating, 100 reviews

The Sunset Suite

The Perfect location for a short drive to Anclote River Park 12 min, where you can enjoy a day at the beach and see some amazing sunsets. Miss Vicki's restaurant on the water for a afternoon lunch or dinner. Rent a boat and go to anclote Island and find some amazing shells. Don't forget The Sponge capital of the world in Tarpon Springs just a 11 minute drive from us. A quiet neighborhood, private suite, with private entrance, for two guest only and no babies, no children, or no pets.

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, 115 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!

Top guest favorite
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
4.91 out of 5 average rating, 123 reviews

Heated Pool • Tarpon & Beaches

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!

Guest favorite
An aerial view captures a cozy lakeside home surrounded by lush greenery and palm trees. The screened-in private pool is visible, along with a nearby dock extending into the water. A fire pit area is seen, providing a space for gatherings. Scenic views enhance the outdoor experience.
Home in Holiday
4.92 out of 5 average rating, 100 reviews

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!

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, 190 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.

Top 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, 80 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

Popular amenities for Holiday vacation rentals

When is the best time to visit Holiday?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$26,362 GYDG$25,944 GYDG$26,153 GYDG$26,153 GYDG$24,061 GYDG$24,688 GYDG$24,061 GYDG$23,015 GYDG$22,596 GYDG$24,479 GYDG$24,061 GYDG$25,525 GYD
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°C

Frequently Asked Questions

  • Do house rentals in Holiday have a kitchen?

    Absolutely! We offer over 100 house rentals with a kitchen in Holiday. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • 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.

  • 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.

  • 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 wifi?

    Absolutely! We offer over 100 house rentals with wifi in Holiday. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Holiday?

    Holiday has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Holiday have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Holiday. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Holiday have free parking?

    Absolutely! We offer over 100 house rentals with free parking in Holiday. Enjoy a tailored experience with all the comforts you desire.

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.

What are the 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.

Quick stats about vacation rentals in Holiday

  • Total vacation rentals

    Explore 120 vacation rentals in Holiday

  • Nightly prices starting at

    Holiday vacation rentals start at G$2,092 GYD per night before taxes and fees

  • Verified guest reviews

    Over 3,870 verified reviews to help you choose

  • Family-friendly vacation rentals

    90 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Holiday vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Holiday rentals

  • 4.8 Average rating

    Holiday stays are highly rated by guests—averaging 4.8 out of 5!

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