Vacation rentals in Holiday

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, 226 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!

Cottage in Tarpon Springs

The exterior of a charming blue bungalow features a pink front door. A pink chair is positioned next to the door, adorned with greenery and colorful florals. The landscaped yard showcases a stone pathway, bordered by plants and palm trees, creating an inviting entrance.

4.94 out of 5 average rating, 89 reviews

Charming Blue Bungalow With Amazing Yard

Don't miss a stay at the Blue Bungalow while enjoying the historic and beachy town of Tarpon Springs. This spacious 2-bedroom 1 bathroom home built in 1936 has been tastefully updated but still has much of it's original charm. Then there's the best backyard in town with a grill, dining area, a fire pit, cornhole court, and a spacious deck! This home is located minutes from several beaches, parks, a dog park and the Pinellas Trail. Restaurants, breweries, and fun community events are abundant.

Cottage in Tarpon Springs

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.

4.98 out of 5 average rating, 122 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!

Superhost

A private solar-heated pool is surrounded by lush greenery, creating a serene outdoor space. Two lounge chairs are positioned poolside, with a small table nearby, inviting relaxation in a peaceful atmosphere.

Home in New Port Richey

4.79 out of 5 average rating, 121 reviews

Pool Paradise - Private Solar Heated Pool

Welcome to your private vacation gateway. Escape to Florida Sunshine Sanctuary in Tampa Bay Area. Our 2 Bedroom/ 2 Bathroom House is nested in a quiet suburb not far from the Tampa Airport. It is 25 miles from the famous Clearwater Beach and 30 miles from the Busch Gardens. Take the ultimate one day trip to DisneyWorld which is a 2 hour drive form the house. Also a 15 min drive to Greektown and Tarpon Springs Sponge Deck. House is nicely decorated with everything needed to create special memorie

4.99 out of 5 average rating, 265 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/Coffee Bar/Fully Stocked

🏡 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, 102 reviews

The modern kitchen features sleek white cabinetry and stainless steel appliances. A spacious island is centered, offering additional countertop space. Natural light is provided by a window above the sink, enhancing the airy feel of the room. Decorative elements include a plant and minimalistic kitchenware.

Home in New Port Richey

Downtown Darling

Bring the whole family to this great property with lots of room for fun. 3 king bedrooms with pillow top mattresses, one bunk bed room that sleeps 3 kids. Large kitchen, large laundry room. Home has been completely renovated. Less than a 10 minute walk to all the activities on Main Street, Restaurants, breweries, roof top restaurant, axle throwing bar, sims park with weekly activities and a brand new playground and splash pad for the kids. Walk in the evening down the river boardwalk.

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, 86 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

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, 129 reviews

Heated Pool • Near Tarpon & Gulf Beaches 5 mi

🌴 Heated private pool oasis (Nov–Mar) 5 mi to Tarpon Springs—ideal to recharge. 🏡 Private patio for BBQ and outdoor time in a quiet area for great sleep. Perfect for families & friends: fast Wi-Fi + workspace, fully equipped kitchen, 🔑 24/7 self check-in, and 🚗 on-site parking. Easy access to Dunedin, Clearwater, Tampa, and beaches (times vary with traffic). ✨ Note: pool heat available Nov–Mar (weather permitting). ⏳ Last-minute promos active—book and lock in your dates!

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, 103 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!

4.91 out of 5 average rating, 11 reviews

A single-story yellow house is set against a partly cloudy blue sky. Lush palm trees and well-maintained shrubs frame the entrance, which features white shutters and a welcoming front door. A paved driveway leads up to the house for easy access.

Home

Lakeside Retreat

Im Lakesideretreat kannst Du Florida von seiner schönsten Seite erleben. Direkt an einem kleinen See gelegen lassen sich Fische, Schildkröten, Otter und natürlich viele Vogelarten direkt vom Garten aus beobachten. Mit dem hauseigenen Tretboot sind kleine Ausflüge in die Seenlandschaft möglich. Umgeben von dichten Palmenherzen bietet der schon angelegte Garten viel Privatsphäre und der Pool lädt zum abkühlen ein.

4.94 out of 5 average rating, 131 reviews

A serene lakeside view is presented from a covered deck, featuring a dining table set with plates and glassware. Two chairs and a colorful lounge chair are visible, with water reflecting the blue sky and surrounding trees in the background.

Guest suite in Lutz

Spacious Lakehouse Suite - Nature Lover's Paradise

Bright, clean & well appointed Private patio entrance Includes bedroom, private bathroom & sitting room with TV, microwave, etc. PLEASE TAKE NOTE: the suite shares walls & closed/locked doors with host's home. Spacious lakeside deck & canoe FOR A PRIVATE/ROMANTIC GETAWAY consider our other listing on the property - Miss Ruby, our fully renovated vintage camper with open-air shower and bath-house.

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, 194 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.

Popular amenities for Holiday vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Holiday's top sights

Anclote River Park

89 locals recommend

Tarpon Springs Aquarium And Animal Sanctuary

108 locals recommend

Key Vista Nature Park

33 locals recommend

Other great vacation rentals in Holiday

5 out of 5 average rating, 27 reviews

Tiny home in Holiday

Modern style tiny house

Adirondack chairs are arranged on a pebbled area facing a tranquil canal, with a sunset casting a warm glow over the scene. The serene water reflects the colorful sky, surrounded by lush greenery and residential homes lining the opposite bank.

4.95 out of 5 average rating, 55 reviews

Holiday fun canal home

4.98 out of 5 average rating, 53 reviews

River Home with Pool, Sunset, Dolphin & Fishing

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, 68 reviews

*NEW* Riverside Retreat w/Pool

A serene lake view is captured at sunset, with soft colors reflecting on the water's surface. Lush greenery borders the edge, framing the scene and creating a peaceful atmosphere. The silhouettes of trees are visible against the evening sky, enhancing the tranquil setting.

4.9 out of 5 average rating, 31 reviews

Cozy Beach Home w/Lake view and Kayak!

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.

4.94 out of 5 average rating, 36 reviews

Relaxing Lake House

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, 51 reviews

Simply Charming

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.