Pet-friendly holiday rentals in Holiday

4.99 out of 5 average rating, 150 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

4.93 out of 5 average rating, 122 reviews

A wooden dock extends over the calm waters of Lake Tarpon, surrounded by lush greenery. The expansive blue sky and gentle waves create a serene ambiance, ideal for enjoying nature. The space offers direct access to the lake, enhancing the outdoor experience.

Home in Palm Harbor

Lakefront home near beaches w/ waterview, pets ok

Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

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, 135 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!

4.97 out of 5 average rating, 232 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, 139 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.

5 out of 5 average rating, 158 reviews

A colorful cottage with a screened lanai rests along a serene river. Kayaks and a floating island are docked nearby, with reflections shimmering on the water. Lush greenery surrounds the property, creating a tranquil outdoor setting ideal for relaxation and recreation.

Cottage in Spring Hill

Screened Lanai /Clear Kayak / Waterfront / Fire Pi

Funky Flamingo River Cottage is a hidden gem on the Weeki Wachee River, designed for fun, relaxation, and adventure. Enjoy a no-see-um screened lanai, a comfy king bed, Smart TVs in every room, and a fully stocked kitchen. Paddle with manatees in our clear kayak, float on the lily pad mat, or unwind by the fire pit. With games inside and out, a hammock, and direct water access, it's the perfect escape—just off the main river, between the State Park and Roger’s Park.

Guest house in Town 'n' Country

4.99 out of 5 average rating, 267 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!

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 Oasis • 5mi 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!

4.86 out of 5 average rating, 134 reviews

A modern kitchen showcases sleek stainless steel appliances, including a refrigerator and oven. White cabinetry and open shelves display glassware and cooking essentials. Counter space is efficiently utilized with a sink and dishwasher, ensuring convenience for meal preparation.

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, 129 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.

4.97 out of 5 average rating, 132 reviews

A bright and airy living space features a comfortable teal sofa, a ceiling fan, and a flat-screen television. An open view connects to the kitchen area, which showcases modern appliances. Natural light filters in through windows, enhancing the spacious ambiance.

Home in Tarpon Springs

Modern 3 Bedroom 2 Bathroom House

Experience the charm of Tarpon Springs from our newly renovated 3-bedroom, 2-bathroom family retreat. Just minutes from Lake Tarpon and a short drive to the iconic Sponge Docks, authentic Greek eateries, Fred Howard Beach, the Pinellas Bike Trail, and countless other local gems.

4.92 out of 5 average rating, 127 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

If you’re planning a trip to Tampa, experience the charm of our private studio designed for couples. Enjoy a secure night’s stay, unwind by the pool, and savor the convenience of a BBQ and outdoor stove. Relax in this serene and stylish space.

Popular amenities for Holiday pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

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.

4.98 out of 5 average rating, 44 reviews

Holiday fun canal home

4.9 out of 5 average rating, 113 reviews

A view of a heated saltwater pool is framed by two lounge chairs, positioned on a grassy area. Red umbrellas provide shade for seating areas, and a spacious patio can be seen in the background, featuring modern outdoor furniture and a neutral-colored house.

Home in Clearwater

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

4.92 out of 5 average rating, 274 reviews

A charming Florida bungalow features a turquoise exterior with natural stone accents. The front porch is accessed by a concrete pathway lined with greenery, including tropical plants. A small entry door and window allow for natural light, framed by neatly placed shutters and landscaping.

Home in Barrington Hills

Wonderful family friendly home in Dunedin FL

4.89 out of 5 average rating, 162 reviews

A tranquil pool area is showcased with a clear swimming pool. Several lounge chairs are positioned nearby, along with a vibrant red umbrella providing shade. A grill is covered and placed next to the pool, while a decorative mat adds a touch of color to the concrete surface.

Home in Port Richey

Your Home away from Home , Nice inground pool.

4.99 out of 5 average rating, 131 reviews

A boat deck is presented with a shaded area featuring a built-in grill and multiple seating arrangements. Lush green grass leads from a paved pathway to the water's edge, while palm trees and tranquil waters create a serene setting.

Home in Hernando Beach

Golf Cart, Kayaks, Pedal Boat Included •Waterfront

4.81 out of 5 average rating, 62 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

4.89 out of 5 average rating, 140 reviews

Home in St. Petersburg

NICE 1 BR/1 BA (+ 2BA W/D). 5 min DT, 10 beach!

4.8 out of 5 average rating, 98 reviews

Home in New Port Richey

Cozy home New Port Richey

Pet-friendly home rentals with a pool

4.97 out of 5 average rating, 162 reviews

A cozy outdoor fire-pit area is surrounded by colorful seating. Decorative stones cover the ground, leading to a grill and the inviting glow of flames. A pool and shaded area can be seen in the background, set against a twilight sky.

Home in Clearwater

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

4.91 out of 5 average rating, 218 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

4.91 out of 5 average rating, 404 reviews

A spacious outdoor entertainment area features a tropical saltwater pool surrounded by a screened enclosure. Colorful loungers in vibrant pink and green are positioned near the pool, complemented by a dining table. A shaded area offers comfort for relaxing in the sun.

Home in St. Petersburg

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Guest house in St. Petersburg

A charming yellow cottage is framed by lush palm trees and tropical plants, featuring a welcoming front door at the end of a paved walkway. Sunlight filters through the greenery, creating a bright and inviting atmosphere near the entrance.

4.9 out of 5 average rating, 142 reviews

St Pete Casita Studio with Salt Water Pool & Yard

4.93 out of 5 average rating, 148 reviews

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.

Home in New Port Richey

Private Pool Mackarosa Tampa Bay.

4.84 out of 5 average rating, 176 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

4.91 out of 5 average rating, 213 reviews

A private outdoor heated pool is framed by a concrete patio, featuring a curved design and clear blue water. Four colorful chairs provide seating around the pool, with additional lounge chairs nearby. A wooden fence offers privacy in the background.

Home in Port Richey

"Wet Feet Retreat" pool home

4.98 out of 5 average rating, 242 reviews

An open living area features a modern kitchen with white cabinetry and a large island with bar seating. A comfortable couch is positioned in front of an electric fireplace, accompanied by a coffee table displaying books and a decorative plant. A wall-mounted TV displays a vibrant underwater scene.

Apartment in Seminole

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

Private, pet-friendly home rentals

5 out of 5 average rating, 9 reviews

Home in Palm Harbor

Harbor Getaway

The collage showcases the cowboy pool surrounded by pebbled landscaping, a cozy bedroom with a spacious bed, a stylish living area with ample seating, and a fully equipped kitchen. Vibrant beach chairs and outdoor games are also visible, highlighting a welcoming atmosphere for relaxation and entertainment.

4.91 out of 5 average rating, 80 reviews

Lazy Day Oasis

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

Waterfront Oasis-Tarpon Sunsets-Pool-Kayak-Fishing

Guest house in New Port Richey

A bedroom features a spacious bed with a dark quilt and illuminated headboard in calming blue tones. Nightstands on either side offer ambient lighting. A ceiling fan is visible above, and a closet with sliding doors is positioned in the background.

4.81 out of 5 average rating, 21 reviews

Comfortable independent room

4.98 out of 5 average rating, 42 reviews

A modern kitchen is showcased with white cabinetry and sleek countertops. Essential appliances include a microwave, coffee maker, and stovetop. An open drawer reveals utensils, while a trash bin is positioned underneath the sink. Natural light is enhanced by recessed lighting.

Tiny home in Port Richey

The Oasis

Guest house in Tarpon Springs

A well-equipped kitchen area is highlighted with light-colored cabinetry and a granite countertop, including essential appliances. A dining table with four chairs complements a cozy seating area with a futon. Natural light filters in through a nearby door leading to the outside.

4.83 out of 5 average rating, 72 reviews

Casa Pina. Cute 1bed 1 bath with patio and king

4.88 out of 5 average rating, 43 reviews

The bedroom features a spacious bed with light bedding and decorative pillows. Nightstands are positioned on either side, each with a lamp. A large framed artwork depicting a beach scene is visible above the bed, complementing the room's calm ambiance.

Flat in Ozona

Palm Harbor Biking, Sunsets & Beaches