Vacation rentals in Holiday

4.99 out of 5 average rating, 105 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

+Spacious family retreat on lake +Free heated pool +Huge last-minute discounts +Big deck, BBQ, dining & firepit +Private backyard lakefront +3 bedrooms, 1 king, 1 queen, 2 twin +3 full baths +Easy to cancel +Pet friendly +Fishing +Games +Quiet serene safe +5 minutes to Gulf sunsets +5 min to Sims Park +20 min to Tarpon Springs +39 min to Tampa airport +50 min to Busch Gardens +5 min to restaurants +Fully equipped kitchen +Free parking & garage +Washer-Dryer +Work area +Hi-speed WIFI +Smart TVs

LocationValueDecor

A screened-in green room features two wooden chairs positioned around a small table, surrounded by various indoor plants. Natural light streams through the slatted roof, illuminating the view of the river visible through the openings in the walls.

4.83 out of 5 average rating, 94 reviews

Riverside Home with Kayaks

My place is a quiet space on the river, on the border of Tarpon Springs and Holiday. The home is on a peninsula, so you will have a view of the sunrise over the river in the back yard, and a view of the sunset over the river in the front yard. It has 6 kayaks available to go exploring the little islands, a sun room, a dock on the water, and an outdoor patio as well as a beautiful screened in green room. We have 2 queen beds, 2 cots with mattresses, and a futon in the sun room. Enjoy your escape!

ValueFamilyTV

5.0 out of 5 average rating, 30 reviews

Home in Tarpon Springs

Reel Retreat | Lakefront Home with Hot Tub

Reel Retreat is a stylish mid-century lakefront escape on Lake Tarpon, perfect for a relaxing getaway. This spacious 3-bedroom, 2-bath home features an open layout, game area, and thoughtfully designed spaces. Take in breathtaking lake views, unwind on the wraparound deck, soak in the hot tub, or gather by the fire pit. With a hammock, grill, and dock access, it’s the perfect spot for peaceful mornings and stunning sunsets. 2 kayaks on property for the lake.Come stay with us for a reel retreat!

LocationFamilyLong stay

A tranquil poolside view captures the serene waters of the Anclote River at sunset. Soft purple lighting reflects from the pool's surface. Spacious seating areas invite relaxation, with silhouettes of boats visible in the background against the vibrant sky.

4.96 out of 5 average rating, 111 reviews

Paradise!Renovated waterfront pool home.Sunsets!

Sunsets to die for! Remodeled in 2023 pool house on the Anclote River with access to the Gulf of America.Imagine fishing,kayaking in the backyard & and spotting dolphins!Watch birds, ducks, manatees. All new appliances and granite countertops. New quartz bathroom cabinets!New tiles throughout the house including Florida room. Cooler,chairs&umbrella, kids beach toys. Fishing rods.Bonfire pit.Grill.Heated pool for a fee. Portable crib,stroller, high chair. Come,relax&enjoy No hurricane damage!

LocationFamilyAir conditioning

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, 92 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

LocationFamilySleep quality

A serene view from the screened lanai highlights a private heated pool, reflecting the soft colors of a sunset. The tranquil waters of the Anclote River can be seen beyond the pool, framed by lush greenery and trees along the riverbank.

4.98 out of 5 average rating, 66 reviews

River Home Heated Pool, Sunset, Dolphin & Fishing

Welcome to the waterfront oasis situated along the serene banks of Anclote River connecting to the Gulf. Enjoy privacy as no backyard neighbors, just a nature. Step outside to your own private paradise, where a screened lanai awaits with a private heated pool. Spend your days lounging poolside, soaking up the Florida sunshine, or marveling at dolphins and manatees. Close driving distance to the world famous beaches (Clearwater, Honeymoon Island), Tarpon Spring, Weeki Wachee & Tampa Bay

LocationFamilyHeating

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.

4.95 out of 5 average rating, 86 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…

LocationFamilyQuiet

4.91 out of 5 average rating, 23 reviews

Cozy Home w/ Fire Pit & Outdoor Lounge

Cozy and stylish home in Holiday, FL perfect for families, couples, or small groups ✨ Enjoy a private backyard with a fire pit, covered patio, and outdoor seating—perfect for relaxing after a beach day. Inside you’ll find comfortable beds, a fully equipped kitchen, fast WiFi, and bright cozy spaces designed to feel like home. Located in a quiet neighborhood just minutes from beaches, restaurants, shopping, and local attractions.

FamilyValuePets

4.98 out of 5 average rating, 120 reviews

Apartment in Holiday

Peaceful Lake Studio Near Tarpon & Beaches

✨ Work, relaxation, or a coastal getaway—you don’t have to choose. Enjoy a private studio for 2 with a queen bed, fast WiFi, workspace, fully equipped kitchen, private parking, and a peaceful lake just steps away. Close to Tarpon Springs, beaches, Dunedin, Clearwater, restaurants, and shops. 🌿 Comfort for work, tranquility for rest, and plenty to explore. Are your dates available? Book now and start enjoying your stay.

FamilyValueParks

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, 121 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!

FamilyValueView

4.84 out of 5 average rating, 19 reviews

Memories

This home is perfect for an extended stay—not just because you’ll enjoy 10% when you book 7 nights or 15% off for monthly stays, but because it has everything you need to feel at home. Enjoy a fully equipped kitchen, laundry room, a lakeview workspace, home gym, and comfortable bedrooms. Cook, work remotely, relax, and enjoy every day in a place designed for long-term comfort. Perfect for families and remote workers.

FamilyLocationCondition

4.88 out of 5 average rating, 104 reviews

Family Coastal Home w/ EV Charger, Bikes &Kayaks

🌴 Enjoy a spacious home perfect for adventure and relaxation! Charge your EV, fire up the BBQ, and make use of the fenced yard with plenty of space for your boat or water toys. Just minutes from historic Tarpon Springs, scenic parks, and beautiful beaches, this home is ideal for hiking, biking, fishing, and kayaking adventures 🛶. This is a single-story property. Relax in comfort after a day full of fun!

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Popular amenities for Holiday vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Holiday's top sights

Tarpon Springs Aquarium And Animal Sanctuary

114 locals recommend

Anclote River Park

97 locals recommend

Key Vista Nature Park

36 locals recommend

Anclote Gulf Park

22 locals recommend

North Anclote Nature Park

6 locals recommend

Boat Club

4 locals recommend

Other great vacation rentals in Holiday

4.93 out of 5 average rating, 14 reviews

Coastal Family Escape w/Heated Pool•Near Beaches

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 22 reviews

Dream Home in Holiday with POOL & SPA and More

ValueLocationQuiet

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.

4.95 out of 5 average rating, 41 reviews

Relaxing Lake House

FamilyLocationCondition

4.83 out of 5 average rating, 60 reviews

Heated Pool, Hot Tub & Sand Volleyball

ValueLocationAccess

4.91 out of 5 average rating, 74 reviews

Remodeled 2BR Near Gulf Beaches Fast Wi-Fi

FamilyLocationBeach

4.93 out of 5 average rating, 15 reviews

Coastal Holiday Home w/Pool - Minutes to Beaches

FamilyCleanlinessIndoor spaces

4.95 out of 5 average rating, 95 reviews

A screened pool area showcases a clear blue pool featuring a dolphin design at the bottom. The surrounding patio is designed with light-colored tiles, and lush greenery is visible beyond the enclosure, contributing to a private outdoor atmosphere.

Home in New Port Richey

Cozy Home, Country Setting, Close to Gulf Beaches

ValueLocationParks

The exterior of the home is shown at night, featuring a well-maintained front yard and a concrete driveway. Soft lights illuminate the entrance, highlighting a welcoming doorway. A black car is parked in front, casting a shadow on the driveway.