House 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, 218 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!

A comfortable living area features a beige sofa adorned with orange accent pillows, flanked by two stylish lamps. A round wooden coffee table is positioned on a decorative rug, with modern wall art enhancing the space. A red armchair adds a pop of color to the setting.

4.96 out of 5 average rating, 102 reviews

Cozy 3-bed home close to beautiful beaches.

Newly updated 3-bedroom, 2-bath home close to everything. Centrally located, within 20-30 mins to the famous Tarpon Springs Sponge Docks, Sunset, Howard Park, Honeymoon Island, Anclote River Park & Clearwater Beaches, Busch Gardens Theme Park and Weeki Wachee. Close toTampa International Airport. Numerous country club golf courses, waterfront restaurants/bars within a short drive. Enjoy your home away from home with everything you need and more with a BBQ Grill/ Fire pit and other amenities.

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.

A comfortable living area is showcased with a beige sofa adorned with colorful pillows and two green accent chairs. A ceiling fan provides airflow, and natural light filters through large windows. The open layout connects to the kitchen area, creating a bright and inviting atmosphere.

4.93 out of 5 average rating, 129 reviews

Cozy Retreat! Walk to Crystal Beach/Park

Cozy Crystal Beach Retreat – Pet Friendly Enjoy this charming 2BR, 1BA home with queen beds and a pull-out sofa. Pets welcome with fee! Relax in the fully fenced backyard with picnic table, perfect for outdoor meals or your furry friend to play. Walk to the water or explore the nearby Pinellas Trail. Just minutes to downtown Dunedin (7 mi), Honeymoon Island (7.5 mi), Clearwater Beach (13 mi), and Tampa Intl Airport (22 mi). Ideal for couples, families, or a relaxing getaway!

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.

4.96 out of 5 average rating, 25 reviews

Cozy Beach Home w/Lake view and Kayak!

Enjoy an entire home, completely renovated located in Holiday, w/Lake view to relax and get away from home. Great locations, near beaches, parks, restaurants, Bush Gardens/Tampa. We have full amenities, full kitchen, living area, fenced yard, Lanai, washer, dryer, workstation w/internet access. Places to explore: -St Nicholas Boat Line -Tarpon Springs Sponge Docks -Tarpon Springs Aquarium -Key Vista Nature Park -Anclote Gulf Park -Anclote River Park

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…

4.96 out of 5 average rating, 115 reviews

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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 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

Spend your holidays in HOLIDAY, FL! We welcome you to our cozy, fully renovated house with a large, heated private in-ground, SALTWATER pool. The house has three bedrooms and enough room for 7 guests, along with two full bathrooms. The kitchen is stocked with all cookware essentials needed. The house has everything you need for vacations, so you may kick back and relax. It is centrally located to many attractions if you're up for a drive.

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!

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!

4.89 out of 5 average rating, 140 reviews

A spacious outdoor area features a heated private pool surrounded by a screened lanai. Lounge chairs are positioned nearby, and a dining set provides a space for meals. Lush greenery is visible in the background, enhancing the tranquil atmosphere.

Home in Tarpon Springs

Game Room, Heated Pool, 5 minutes to Beach

Welcome to the old Florida with a complete modern design renovation. Located on the dead-end street this 1,945 sf house is your perfect gateway to beaches, Florida sunshine and hospitality. Heated private pool will ensure that you can enjoy the outdoors year round and for those rainy days, gather around for a game night or enjoy a game of Foosball, air hockey. Make it a vacation to remember!

Popular amenities for Holiday house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.99 out of 5 average rating, 143 reviews

An aerial view captures a spacious patio surrounding a custom saltwater pool, where lounge chairs are arranged alongside. Lush landscaping features palm trees and flower beds, while a covered seating area, equipped with outdoor furniture, is visible behind the pool. The home showcases a modern design with a sleek metal roof.

Home in Seminole

Tootsie’s Beachside Retreat-New Heated Pool

4.96 out of 5 average rating, 26 reviews

Bahama Behms pool house by the marina

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

An inviting pool lanai is showcased, featuring comfortable lounge chairs and small tables. An umbrella provides shade, enhancing relaxation by the heated pool. A serene lake view is visible beyond the screened enclosure, surrounded by greenery and residential properties.

4.96 out of 5 average rating, 48 reviews

LAKEFRONT HOUSE W/ HEATED POOL

4.89 out of 5 average rating, 163 reviews

Your Home away from Home , Nice inground pool.

A heated pool is surrounded by lush palm trees, providing a sense of seclusion. A stone statue and decorative elements are featured along the pool's edge. Sunlight reflects off the water, creating a serene atmosphere in this private outdoor oasis.

4.99 out of 5 average rating, 146 reviews

Tropical Oasis Retreat w/ Heated Pool

A private pool area features sparkling blue water, surrounded by a well-maintained deck. A wooden pergola offers shaded seating nearby, while tropical plants provide a natural backdrop. The sky is mostly clear, creating a bright and inviting atmosphere.

5 out of 5 average rating, 49 reviews

Florida style home !

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

5 out of 5 average rating, 132 reviews

Coastal Escape: heated saltwater pool & playground

Weekly house rentals

The image showcases a heated in-ground pool bordered by light-colored pavers, overlooking a calm canal. Docked boats and palm trees line the water's edge, reflecting under a clear blue sky. The well-kept lawn adds a touch of green to the serene waterside setting.

4.72 out of 5 average rating, 169 reviews

Gulf Harbors Getaway Home with Pool

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, 50 reviews

River Home with Pool, Sunset, Dolphin & Fishing

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, 84 reviews

Nature Lovers Retreat

4.89 out of 5 average rating, 74 reviews

Finca Vigia

A single-story beach house is presented with a well-maintained front lawn. A covered porch with decorative details is visible, alongside a driveway leading up to the entrance. The exterior showcases a fresh coat of paint, complemented by surrounding greenery.

4.98 out of 5 average rating, 80 reviews

Blue Seahorse

A swimming pool is surrounded by palm trees, offering a refreshing atmosphere. The clear water reflects the blue sky, and a glimpse of the waterfront is visible beyond the pool area. The serene setting encourages relaxation and enjoyment.

4.99 out of 5 average rating, 85 reviews

Waterfront Pool Dock Golf Boat Rent Beach 2K/2T/2b

Superhost

The living room features two comfortable sofas adorned with yellow accent pillows. A coffee table is centered in front of the seating area, while a large wall-mounted Smart TV displays various streaming options. Natural light filters in through a set of windows, enhancing the inviting space.

4.81 out of 5 average rating, 64 reviews

‘Boho bungalow’ Holiday home 2/1.5 up to 4 guests

Superhost

4.79 out of 5 average rating, 19 reviews

3bed 2bath updated modern home!

Private house rentals

A spacious living area showcases a light-colored couch adorned with bright blue cushions. A flat-screen television is mounted on a wall opposite a wooden media console. A tall floor lamp and green plants add a touch of nature to the relaxing decor.

5 out of 5 average rating, 13 reviews

Spacious Tropical Vibes-King Bed/Private Back Yard

4.96 out of 5 average rating, 27 reviews

The living room features a brown leather sofa accompanied by a blue accent chair, all set on a patterned area rug. A round coffee table sits in the center, and a pendant light hangs overhead. A framed picture and a potted plant add decor against the light walls.

Home in Tarpon Springs

Poinsettia Place A, Tarpon Springs! Fully Fenced!

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.

4.94 out of 5 average rating, 98 reviews

Downtown Darling

Two orange kayaks are positioned on the grassy bank near calm waters, ready for exploration. A dock with steps leads down to the water, surrounded by lush greenery. Clear blue skies add to the inviting atmosphere for a day of paddling.

5 out of 5 average rating, 13 reviews

Lakeside Escape w/ Kayaks, Firepit & BBQ!

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

4.95 out of 5 average rating, 87 reviews

Private pool, Golf Cart, Completely Renovated!

Superhost

The exterior of the property is shown, featuring a light-colored house with a welcoming entrance. A paved driveway leads to a garage, surrounded by neatly arranged white stones and potted plants. The sky is mostly clear with scattered clouds.

4.81 out of 5 average rating, 27 reviews

The Melody Hideaway

4.98 out of 5 average rating, 51 reviews

A fully equipped kitchen features modern appliances, a large island with seating for two, and ample storage cabinets. Natural light enters through the nearby windows, illuminating the clean and functional design, while decorative shelves display kitchenware and cooking essentials.

Home in Tarpon Springs

Freshly Renovated 1925 Bungalow

A spacious living area is shown, featuring a large grey sectional sofa and a wooden entertainment unit with a flat-screen TV. Light-colored walls enhance the bright atmosphere, while a dining table with chairs is positioned in the background, complemented by wood-style flooring.