Vacation rentals in Holiday

5 out of 5 average rating, 227 reviews

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

The Bohemian Studio Countryside Gem Separate Entry

🚨 Unbeatable Deal! Secure a serene, countryside escape at an AMAZING PRICE (Nov-Feb) This cozy studio offers total PRIVACY with self-check-in & a separate entry. Enjoy a PEACEFUL stay minutes from hospitals, dining, springs, & beaches 🌳 2 Acres & Fenced Patio 🍳 Fully Equipped Kitchen and bathroom 💻 High-Speed Internet & FREE Netflix 🚗 Ample FREE Parking Zero Hidden Costs Perfect for traveling nurses, snowbirds, or a romantic escape. Experience comfort and book your stress-free getaway now

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, 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.

4.86 out of 5 average rating, 7 reviews

A bright and inviting bedroom features a spacious bed adorned with a colorful quilt and decorative pillows. Natural light fills the room through a window, complemented by vibrant orange curtains. A bedside lamp and wall art add character to the cozy space.

Guest suite in Holiday

Cheery Private Room Efficiency-Kitchenette

Normally host long-term stays. Bright, cheery guest suite in house with kitchenette amenities. A cozy space suitable for 1 person. Take a break, unwind at this peaceful retreat. Close to Anclote Park Beach (Gulf). 15-min walk to Key Vista Nature Park walking trails. Close walk to Rec Complex (tennis/pickle ball courts, paddle ball courts). Nr Tarpon Springs & Howard Park Beach & kayaking. Short distance to Clearwater Beach, Busch Gardens, 2 hours Walt Disney World & Universal.

A serene view of the Anclote River at sunrise, with a coffee cup placed on the dock's edge. The sun is seen rising above the water, reflecting golden hues on the surface. Lush trees frame the scene, creating a peaceful atmosphere.

4.9 out of 5 average rating, 20 reviews

Anclote Oasis-Sunsets-Pool-Kayak-Fish-Gulf Access

Last Min December/January Date Sale!! Come choose your pleasure; take a swim in the saltwater pool, fish from the dock, kayak or take a boat ride to the islands. Or you might just relax and watch sports on the 50”TV overlooking the Anclote River. This home brings room for the family, all the necessities and a quick drive or bike ride to Tarpon Springs. Watch Birds, Dolphin & Manatee from the dock. Beautiful sunrises and sunsets from the backyard. Great location for traveling!

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.

4.96 out of 5 average rating, 67 reviews

*NEW* Riverside Retreat w/Pool

Take it easy at this unique and tranquil getaway. Welcome to our Riverside Retreat where you will enjoy incredibly relaxing peaceful days, and sunset views. Recently renovated 2 Bedroom, 2 Full Bathroom, pool home with dock and privacy fenced backyard on the Anclote River. This home is fully equipped and is ready for you to enjoy. Conveniently located and only a 9-minute drive to the World-famous Sponge Docks and minutes from our award winning beaches…

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.

4.9 out of 5 average rating, 29 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, 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!

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.

4.97 out of 5 average rating, 32 reviews

Relaxing Lake House

Take it easy at our tranquil getaway. Observe local and migrating birds right from the backyard, fish from the dock, or just relax and enjoy the view from the screened in porch. Minutes from New Port Richey and Tarpon Springs famous Sponge Docks and less than an hour from all the Tampa attractions and Clearwater Beach. Take a day hike at Honeymoon Island Osprey and Pelican Trail and end the hike with a swim at the beach.

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.

4.92 out of 5 average rating, 101 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!

Guesthouse in New Port Richey

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.

5 out of 5 average rating, 192 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.

4.99 out of 5 average rating, 80 reviews

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

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

Guesthouse in New Port Richey

4.96 out of 5 average rating, 52 reviews

Cotee River Cottage in the Woods

This peaceful cottage with queen bed and full bathroom is the perfect spot for a writer’s retreat or couple’s getaway. Centrally-located close to downtown New Port Richey yet tucked into lush riverine subtropical forest, you are steps away from the beautiful tannin waters of the upper Cotee River.

Popular amenities for Holiday vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Holiday's top sights

Anclote River Park

87 locals recommend

Tarpon Springs Aquarium And Animal Sanctuary

106 locals recommend

Key Vista Nature Park

31 locals recommend

Other great vacation rentals in Holiday

The collage showcases the cowboy pool surrounded by pebbled landscaping, a cozy bedroom with a spacious bed, a stylish living area with ample seating, and a fully equipped kitchen. Vibrant beach chairs and outdoor games are also visible, highlighting a welcoming atmosphere for relaxation and entertainment.

4.91 out of 5 average rating, 80 reviews

Lazy Day Oasis

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.

4.95 out of 5 average rating, 218 reviews

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

4.99 out of 5 average rating, 238 reviews

Home in Port Richey

Quiet Neighborhood / All Essentials Provided

A charming single-story home is set within a well-kept yard, featuring a vibrant red brick exterior. The front porch includes seating for relaxation, while a garage accommodates a vehicle. Lush greenery surrounds the space, enhancing the inviting atmosphere.

4.86 out of 5 average rating, 49 reviews

Simply Charming

4.98 out of 5 average rating, 125 reviews

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

Cypress Lakes Barn Retreat

5 out of 5 average rating, 7 reviews

Home in New Port Richey

NEW Steps to Downtown • 7 Mins to Beach + Parking

A sparkling saltwater pool is featured in the backyard, with a gently curving shape and a clear blue surface. The area is fenced for privacy, with a well-maintained lawn and a sunny sky visible above.

4.97 out of 5 average rating, 97 reviews

Private 3 Bedroom House w/ Heated SaltWater Pool

A dolphin is captured leaping from the water, creating splashes as it breaks the surface. The serene Anclote River serves as a backdrop, with distant docks and lush greenery lining the shore.