Pet-friendly holiday rentals in Holiday

4.99 out of 5 average rating, 160 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

Tiny home in Tarpon Springs

A serene sleeping area features a large bed adorned with multi-colored striped blankets and a cozy yellow throw. Natural light fills the space through two windows, illuminating the wooden accents and white walls.

4.87 out of 5 average rating, 286 reviews

Driftwood Surf Shack

This unique Surf Shack is a guest home that sleeps 2 adults & 2 children futon sofa . There is plenty of room to relax inside or outside on the large wood deck situated under a beautiful oak tree. Located in the historic district Tarpon, just blocks from Downtown, the famous Sponge Docks & Craig Park where you can watch dolphins feed at sunset in the many Bayous. Close to beaches, shopping, restaurants, breweries, boat excursions, water sports & the Pinellas Trails you will never get bored.

4.98 out of 5 average rating, 241 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.

4.94 out of 5 average rating, 143 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

Welcome to Gemini Place, a cool, quiet 2/2 filled with an easy charm. This solid 1,100- sq. ft house is in the heart of old Tarpon and is a perfect, simple escape for a few days, a few weeks or longer. The north-facing house sits on a one-way brick street and is an easy walk to everything in this quaint, Greek-flavored town. We are close to some of the best beaches in the U.S. We're pet friendly but do have restrictions and a fee that is determined by several factors. Please inquire.

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, 132 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!

Guest house in Town 'n' Country

4.99 out of 5 average rating, 290 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, 125 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 • Near Tarpon & Gulf Beaches 5 mi

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, 102 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!

Guest house in Safety Harbor

A modern living space features a comfortable blue sofa adorned with decorative cushions. A sleek coffee table with a candle sits in front. The open kitchen showcases contemporary cabinetry and a kitchen island with bar seating. Light fixtures illuminate the area, enhancing the inviting ambiance.

4.98 out of 5 average rating, 109 reviews

Luxe Apartment | Water Views | Covered Balcony

Upscale, comfortable suite located within central Safety Harbor. This beautiful apartment is great for a quick getaway or a longer vacation rental. Located steps away from Bayshore Blvd which borders Tampa Bay and a 10-minute walk to Main Street Safety Harbor. Beautifully professionally designed contemporary and comfy décor. Easily walk to many restaurants, breweries, and shops!

4.95 out of 5 average rating, 180 reviews

Two bright yellow chairs are positioned across from each other on a patterned area rug. A small round table with a decorative design sits between them. A cozy sleeping area is visible in the background, featuring a bed with light-colored bedding and framed artwork on the walls.

Guest suite in Tampa

Renovated chic Parisian studio

Perfect for a couple or a couple of friends! Our studio is vibrant, modern, and a fun take on Parisian interior style. ***The studio is a private unit of a standing triplex house with its own entrance. Located in a central area of Tampa. 10 minutes from the airport, 30 minutes from our beaches, and 20 minutes from Downtown!

4.86 out of 5 average rating, 140 reviews

The bedroom features a spacious bed with soothing neutral bedding, paired with accent pillows. A stylish desk sits beside the bed, enhanced by natural light from a nearby window. A ceiling fan and mounted TV add convenience, while decorative wall art complements the modern design.

Home in Tarpon Springs

MODERN/Mins to Beach/walk to dwtn/Free parking

🌴 Escape to Tarpon Springs! This newly renovated 1B/1B private home is perfectly located—just 5 minutes to the beach and the famous Sponge Docks, and a short stroll to charming downtown. Whether you’re here to relax, explore, or soak in the local culture, this getaway puts you right in the heart of it all.

4.91 out of 5 average rating, 132 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.

Flat 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

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.96 out of 5 average rating, 47 reviews

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.

Home in Forest Hills

Holiday fun canal home

A charming farmhouse exterior is showcased under large trees, with a welcoming front porch featuring red seating and decorative plants. A spacious gravel parking area is visible, complemented by a green landscape in the background, enhancing the tranquil setting.

4.92 out of 5 average rating, 143 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

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

4.89 out of 5 average rating, 164 reviews

Home in Port Richey

Family 2BR Oasis w/Private Pool & HDTV, PAWsitive

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, 119 reviews

Waterfront house near Gulf of Mexico

4.82 out of 5 average rating, 65 reviews

Home in Holiday

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

4.78 out of 5 average rating, 9 reviews

Home in Port Richey

Pet friendly, Waterfront, Kayak, Fire pit, Game Rm

4.94 out of 5 average rating, 101 reviews

A spacious living area features a large TV mounted on a green accent wall, complemented by wooden flooring. Natural light enters through a window adorned with flowing curtains. A coffee table sits at the center, surrounded by comfortable seating and a decorative plant.

Home in St. Petersburg

Charming Of Sand and Sea Home

Pet-friendly home rentals with a pool

4.91 out of 5 average rating, 129 reviews

A private pool area is featured, enclosed by a screened structure that allows for natural light. The serene water is illuminated by sunlight, while the surrounding space is finished with a smooth surface. A comfortable seating area is seen in the distance, accompanied by nearby decorative landscaping.

Flat in Land O' Lakes

Studio with Pool

4.91 out of 5 average rating, 219 reviews

The spacious studio cabin features wooden accents and high ceilings with exposed beams. Large windows allow natural light to fill the room. A comfortable sofa, a flat-screen TV, and a queen bed are present, alongside a small side table and two chairs.

Flat in Dunedin

Downtown Dunedin B&B - Rustic Cabin Studio with He

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, 138 reviews

Private pool suite in heart of Tarpon Springs!

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

4.93 out of 5 average rating, 148 reviews

Home in New Port Richey

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.

Flat in Tampa

Private apartment perfectly located in Citrus park

4.98 out of 5 average rating, 247 reviews

Apartment in Seminole

SHEEK and Glam- heated pool Updated! 3 mi to beach

4.95 out of 5 average rating, 191 reviews

A serene pond is surrounded by tropical plants and lush greenery. Water lilies float on the surface, while a few decorative rocks enhance the natural ambiance. In the background, a private porch area is visible, complementing the tranquil outdoor setting.

Flat in Dunedin

Mermaid cottage

Private, pet-friendly home rentals

5 out of 5 average rating, 16 reviews

Harbor Getaway

Holiday home in Port Richey

4.87 out of 5 average rating, 31 reviews

Family home

4.96 out of 5 average rating, 57 reviews

A spacious living area is furnished with two comfortable sofas and a coffee table, complemented by a decorative rug. Artwork featuring seashells adorns the walls, and a large television provides entertainment. Natural light flows through the numerous windows, enhancing the open atmosphere.

Home in New Port Richey

Waterfront Getaway w/ Dock & Kayaks – Dog Friendly

4.9 out of 5 average rating, 21 reviews

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.

Home in Forest Hills

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

Holiday home in New Port Richey

4.9 out of 5 average rating, 91 reviews

River Side Home. Three mins to Downtown.

4.96 out of 5 average rating, 93 reviews

A well-equipped kitchenette features a granite countertop with three bar stools. Natural light enters through a window, illuminating the space, which is complemented by a small dining area and a comfortable seating arrangement. A wall-mounted TV and a lamp add to the cozy ambiance.

Farm stay in Odessa

Cabin 3 - Nasturtium Nest

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.

4.96 out of 5 average rating, 24 reviews

Waterfront Gem Near Clearwater • Swim Spa + Nature