Pet-friendly holiday rentals in Holiday

Home in Sea Ranch on the Gulf

The exterior of a freshly redone home is visible, featuring a combination of yellow siding and stone accents. A welcoming sign is positioned near the entrance, surrounded by colorful flower beds with various blooms and maintained landscaping, creating an inviting approach to the property.

4.86 out of 5 average rating, 118 reviews

Waterfront house near Gulf of Mexico

Freshly redone home that is yours to enjoy. 2 bedrooms and 2 bathrooms that can accommodate 4 guests. Enjoy the gorgeous sunsets from either the screened-in back porch or the dock on the canal. Or, jump into the kayak and paddle a very short distance (7 houses down the canal) to the Gulf of Mexico. Fishing tackle and poles are available. Friendly, quiet neighborhood that is great for walking or riding the bikes that are included with the house. Plenty of restaurants or shopping nearby.

4.99 out of 5 average rating, 156 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

4.97 out of 5 average rating, 239 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Guest suite in Tarpon Springs

A heated saltwater pool is surrounded by lush tropical landscaping, with clear blue water reflecting the sky above. A colorful float rests on the water's surface. The screened enclosure provides a barrier while allowing for views of the serene outdoor space.

4.96 out of 5 average rating, 136 reviews

Private pool suite in heart of Tarpon Springs!

Charming private suite in a safe, serene neighborhood—just minutes from beaches, Downtown Tarpon, Sponge Docks & Sunset Beach! Your cozy retreat features a private entrance, queen bed, fast WiFi, cable television, a full kitchen & heated in-ground pool. Explore Tarpon Springs and the Pinellas Trail on provided bikes, then unwind at Sunset Beach with provided beach towels, chairs, umbrellas, toys, cooler & sunscreen. This space is a perfect blend of comfort, convenience & coastal charm!

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, 128 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!

Guesthouse in Town 'n' Country

4.99 out of 5 average rating, 280 reviews

Entire Guest House near Tampa airport

Welcome to our charming guest house! Located just 12 minutes away from Tampa Airport, 20 minutes from Raymond James Stadium, and a quick 35-minute drive from Clearwater, our entire guest house offers you convenience and comfort. With a private entrance, you'll have all the privacy you need. Whether you're here for a game, a beach getaway, or to explore the city, our cozy space is your perfect home base. Book now for an unforgettable stay!

4.91 out of 5 average rating, 123 reviews

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

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!

4.92 out of 5 average rating, 100 reviews

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

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, 162 reviews

Your Home away from Home , Nice inground pool.

Nice 2 bedroom,, 2 bath 1 shower 2 bath tubs ,,,,pool home pool is not heated. ,,,. Fully furnished , great neighborhood . Nice one car garage huge island kitchen . Within. 3 miles to shopping , malls , restaurants . Great location. Hudson beach, sunwest beach, casino boat, weeki wachee springs , all close by .pets fees 115.00 non refundable max 2 pets 30 lbs under pets must be on reservation

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, 145 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

The kitchen features modern appliances, including a stove and microwave, along with ample counter space and open shelves holding dishes and cooking essentials. A sink is positioned beneath a window, while light streams into the room, creating a bright and functional cooking area.

4.91 out of 5 average rating, 143 reviews

1 block to dwnt/7min beach/King bed/Free parking

✨ Modern Coastal Retreat in Downtown New Port Richey Enjoy this beautifully remodeled 1-bedroom private unit just steps from historic downtown and minutes to the beach. Everything is brand new, with a fully equipped kitchen, stylish living space, and a comfortable king bedroom with TV for relaxing nights in.

4.91 out of 5 average rating, 130 reviews

A compact bedroom features a neatly made bed adorned with decorative pillows. A small nightstand with a lamp is positioned beside the bed. Wall art depicting floral designs enhances the room's decor. A fan hangs from the ceiling, providing airflow.

Apartment in Port Richey

La Palma

Welcome to La Palma New apartments is very quiet place, WiFi , kitchen, free parking, close to the beach and nice Restaurant, 45 minutes from the Tampa Airport, 5 minutes to New Port Richey Downtown. Maximum of 2 Pets are allowed but there is $100 fee for pets, to stay in for a later checkout is a $20 fee.

Popular amenities for Holiday pet-friendly home rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.95 out of 5 average rating, 41 reviews

Home in Spring Hill

Luxury getaway, Heated Pool, Weeki Wachee

The outdoor area features a fully enclosed heated pool with a spacious deck. Lounge chairs and tables surround the pool, while string lights add a subtle ambiance. Large sliding glass doors offer a view of the indoor spaces, enhancing the connection between indoor and outdoor living.

4.93 out of 5 average rating, 88 reviews

Heated pool, golf, grill! Fun-Packed Family Oasis

4.94 out of 5 average rating, 140 reviews

The entrance features a white gate leading to a small front porch. Surrounding greenery and colorful plants are positioned along the walkway. Two windows with shutters provide natural light to the entryway, complemented by a decorative flamingo and a welcoming doormat.

Home in Tarpon Springs

Our Gemini Place: Comfort & Charm in Old Tarpon

A spacious living area is highlighted by a large wall-mounted television displaying vibrant underwater scenes. Two tall planters with decorative branches frame the television. A modern entertainment unit holds an electric fireplace, while a round coffee table sits at the center of the cozy seating arrangement.

5 out of 5 average rating, 5 reviews

2 Bed 2 Bath Remodeled House Palm Harbor

4.81 out of 5 average rating, 64 reviews

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.

Home in Holiday

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

5 out of 5 average rating, 14 reviews

A charming house with a screened porch is surrounded by lush greenery and mature trees, providing ample shade. Potted plants line the entrance, adding a touch of color to the soft beige exterior. A gravel path leads to the house, enhancing the welcoming outdoor appeal.

Home in Tarpon Springs

Anclote River Casita#3

4.88 out of 5 average rating, 75 reviews

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.

Home in Forest Hills

Dolphin-Watch Waterway – Pool/Spa Escape Tarpon

4.8 out of 5 average rating, 103 reviews

Cozy home New Port Richey

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 191 reviews

An outdoor tiki hut porch is illuminated by soft string lights. Comfortable seating creates a cozy gathering area, surrounded by lush greenery. A wooden dining table sits in the center, offering a relaxed space for meals or conversation.

Guesthouse in Dunedin

Tiki Hut Cottage

4.9 out of 5 average rating, 115 reviews

Home in Clearwater

Beach or Golf Getaway • Heated Pool/Spa • Pets OK

Cottage in Indian Rocks Beach

An inviting heated saltwater pool is softly lit in the evening, surrounded by sun loungers. The vibrant mural features a large tropical flower. A close-up shows a decorative pillow with the word 'SUNSET.' The living area offers a cozy seating arrangement with colorful cushions and a decorative coffee table.

4.96 out of 5 average rating, 167 reviews

Luxury Beach Bungalow | Walk to Dining & Sunset

Holiday home in New Port Richey

4.9 out of 5 average rating, 90 reviews

River Side Home. Three mins to Downtown.

The backyard features a solar panel heated swimming pool, enclosed by a screened area to deter insects. Lounge chairs are positioned nearby, providing space for relaxation. A colorful inflatable float and a green ball are present in the water, adding a playful touch to the serene setting.

4.93 out of 5 average rating, 148 reviews

Private Pool Mackarosa Tampa Bay.

4.84 out of 5 average rating, 177 reviews

A private entrance is visible, featuring a clean white gate that leads into the apartment area. A paved walkway of gray stones is bordered by white gravel and greenery, creating an inviting access point. Nearby structures can be seen, emphasizing the neighborhood's quiet environment.

Apartment in Tampa

Private apartment perfectly located in Citrus park

Condo in Gulf Island Beach and Tennis Club

A spacious living area features a dark sectional sofa and a large flat-screen television. Brightly colored artwork adorns the walls, and a glass coffee table adds a modern touch. Natural light enters through a sliding glass door, with views of the outdoor patio.

4.91 out of 5 average rating, 103 reviews

Florida Breeze

4.93 out of 5 average rating, 54 reviews

A private pool area is showcased with a clear blue pool surrounded by a deck. Lounge chairs are positioned nearby under a shaded canopy, while a seating area with a canopy is visible in the background. Lush greenery frames the scene, enhancing the space.

Guest suite in Holiday

Peaceful Meadows

Private, pet-friendly home rentals

4.83 out of 5 average rating, 53 reviews

Stunning *Newly Remodeled Riverfront Oasis - Kayak

4.81 out of 5 average rating, 27 reviews

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.

Home in Holiday

The Melody Hideaway

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.

4.96 out of 5 average rating, 95 reviews

Beachy 3 Bedroom Hot Tub and Saltwater Pool

4.84 out of 5 average rating, 37 reviews

A welcoming entrance is framed by lush greenery, featuring a set of two outdoor chairs positioned in front of a door. The concrete pathway leads to the door, with small flowering plants visible alongside the entrance.

Condo in Tarpon Springs

New Cozy bayou vista view condo.

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, 78 reviews

Charming Blue Bungalow With Amazing Yard

A serene outdoor space is illuminated by string lights hanging from trees. A winding stone path leads to wooden steps ascending to a deck. Lush green grass surrounds a picnic table positioned on one side, enhancing the tranquil atmosphere of the lakefront setting.

4.95 out of 5 average rating, 22 reviews

Waterfront Gem Near Clearwater • Swim Spa + Nature

A decorative fountain with three tiers is prominently featured in the yard, surrounded by colorful flowers and greenery. The home’s entrance is framed by large arched windows, and the pathway leads to a welcoming entryway, enhancing the overall curb appeal.

4.91 out of 5 average rating, 35 reviews

“The Fountain Palm” Pool Home