Pet-friendly holiday rentals in Holiday

4.99 out of 5 average rating, 251 reviews

The tiny home is set amidst a lush forest backdrop, featuring a welcoming entrance that is framed by large windows. A spacious wooden deck is adorned with comfortable seating, including two bright blue chairs and two red chairs. A black hammock hangs between trees, inviting relaxation.

Campsite in Thonotosassa

The Palm Tree Getaway

Ever stayed the night in the woods? Cross it off the bucket list with our ‘tiny-house’ style stay near the Hillsborough State Park. Rated #7 on PureWow as one of the 20 Best Airbnb Cabins. This brand new luxury tiny home was thoughtfully crafted to capture the natural beauty of its old Florida virgin forest surroundings. Glamping at its finest with the best modern conveniences like a full gourmet kitchen, spa like shower, 1G FiberWi-Fi Internet, TV, and a super quiet Mini SplitAC & Heating.

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.

4.85 out of 5 average rating, 116 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, 139 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

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, 134 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, 224 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.

4.93 out of 5 average rating, 137 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.

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.

4.88 out of 5 average rating, 271 reviews

Driftwood Surf Shack

This unique Surf Shack is a guest home that sleeps up 4 & still 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 in this town!

4.98 out of 5 average rating, 187 reviews

A spacious backyard is highlighted by a hammock suspended between two trees, inviting relaxation. A black dog and a tan dog can be seen exploring the grassy area, surrounded by tall trees adorned with Spanish moss. A guesthouse is visible in the background.

Farm stay in Odessa

Farm and lake stay at Malfini Cay

PRIVATE GUESTHOUSE...Lakefront -full kitchen living room-very large bedroom-full bath-2.5 acres. Newly decorated/remodeled. 2 flat screen TVs-Roku (Netflix and Spectrum app)-WIFI -laminate flooring-high thread count sheets-comfy queen bed. IKEA sleeper sofa in livingroom. All kitchen appliances with coffee bar/Keurig-W/D. Wooded setting-beautiful views of ski lake. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

4.92 out of 5 average rating, 98 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 Private 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!

4.91 out of 5 average rating, 138 reviews

The living area displays a comfortable brown couch adorned with soft green cushions, positioned near a rustic wooden coffee table. An open-concept kitchen is visible, featuring modern fixtures and shelving, with a dining area that includes two stools. Natural light filters through a window, enhancing the space.

Home in New Port Richey

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

✨ Modern Villa in New Port Richey. Enjoy this beautifully remodeled 1-bedroom villa, fully equipped with everything you need for a comfortable stay. Nestled within walking distance of historic downtown and just minutes from the beach, this stylish retreat offers the perfect blend of convenience and relaxation. Everything inside is brand new, making it the ideal home base for your getaway.

4.91 out of 5 average rating, 118 reviews

Home in Forest Hills

Heated Pool Getaway · 5mi Tarpon & Beaches

Private pool oasis near Tarpon Springs, Dunedin, Clearwater & Tampa. Built for families/friends: fast Wi-Fi, workspace, equipped kitchen, BBQ patio and chill areas. Self check-in 24/7 and free parking. Close to beaches and nature parks for walks and exploring. Quiet for sleep; practical for work. Last-minute deals live this week. Book today and enjoy your own pool.

4.91 out of 5 average rating, 127 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

A screened-in area features a wooden dining table surrounded by four sturdy chairs. Comfortable chairs with blue cushions sit in a corner, while a decorative rug in light blue adds a calm touch. Wall art reflecting a beach theme is displayed, creating a relaxed atmosphere.

4.87 out of 5 average rating, 70 reviews

Elegance & Ease: Your Comfortable Stay

4.85 out of 5 average rating, 105 reviews

A living area features comfortable seating arranged around a central coffee table. A large television is mounted on the wall opposite the sofas. Bright yellow accents are included in the decor, complemented by a vibrant blue chair and decorative pillows.

Home in Tarpon Springs

Adorable 3 Bedroom Family Getaway

4.91 out of 5 average rating, 270 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

4.96 out of 5 average rating, 50 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

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.

4.89 out of 5 average rating, 160 reviews

Your Home away from Home , Nice inground pool.

4.99 out of 5 average rating, 142 reviews

A welcoming exterior view of the house, featuring a landscaped front yard with palm trees and decorative rocks. A large driveway leads to a garage, while outdoor seating is visible on a covered porch, framed by large windows and soft natural light.

Home in Palm Harbor

Tropical Oasis Retreat w/ Heated Pool

4.84 out of 5 average rating, 144 reviews

A side view of the duplex showcases a light grey exterior with landscaped front yard featuring varied plants and stones. A small pathway leads to the entrance doors, with a driveway visible at the back of the unit. Nearby trees provide a natural setting.

Home in Largo

SeaSalt Gray Cottage 1 - few miles to beaches

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.

4.91 out of 5 average rating, 212 reviews

"Wet Feet Retreat" pool home

Pet-friendly home rentals with a pool

4.96 out of 5 average rating, 176 reviews

Home in Palm Harbor

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

Apartment in Land O' Lakes

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.

4.92 out of 5 average rating, 120 reviews

Studio with Pool

4.96 out of 5 average rating, 190 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

4.96 out of 5 average rating, 130 reviews

An outdoor screened area features a private heated pool surrounded by a spacious deck. Two lounge chairs are positioned nearby, with a barbecue grill present for outdoor cooking. A dining set with multiple chairs is also visible under a covered patio, providing shade and comfort.

Home in Spring Hill

Weeki Wachee Springs heated pool home retreat

4.97 out of 5 average rating, 187 reviews

Home in St. Petersburg

Beach Vacation Dream Pool Home-5 Mins to Beach

4.92 out of 5 average rating, 224 reviews

A heated pool is enclosed by a screened lanai, featuring a unique shape with a brick border. Lounge seating is present around the pool, while a hammock is visible in the background. The tranquil area is surrounded by high wooden fencing for privacy.

Home in Tampa

Rooms with a Pool

4.97 out of 5 average rating, 118 reviews

A viewing deck equipped with several white chairs overlooks calm waterways. A small boat and two kayaks are visible at the dock, surrounded by lush reeds and gentle water reflections under a bright blue sky.

Home in Hernando Beach

Saltwater Pool • Kayaks • Pedal boat + more!

4.98 out of 5 average rating, 238 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.

Condo in Seminole

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

Private, pet-friendly home rentals

4.79 out of 5 average rating, 28 reviews

Villa in New Port Richey

Sleeps 6•Near Beach•PS4•PingPong/Billiard•FirePit

4.9 out of 5 average rating, 20 reviews

Home in Forest Hills

Waterfront Oasis-Tarpon Sunsets-Pool-Kayak-Fishing

A spacious pool area is enclosed by a screened lanai, featuring a glistening blue pool. Lounge chairs are positioned along the poolside, and a dining table with several chairs is visible in the background, allowing for outdoor gatherings.

4.97 out of 5 average rating, 39 reviews

Angie's Family-Fav Lake Home: Heated Pool 3br/3ba

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.

4.93 out of 5 average rating, 73 reviews

Charming Blue Bungalow With Amazing Yard

Guesthouse 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.

4.86 out of 5 average rating, 66 reviews

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

4.95 out of 5 average rating, 87 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

5 out of 5 average rating, 12 reviews

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.

Home in Palm Harbor

Waterfront Gem Near Clearwater • Swim Spa + Nature