Pet-friendly vacation rentals in Holiday

4.92 out of 5 average rating, 271 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

Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi State park & Clearwater Beach and Clearwater Aquarium. Large kitchen, dining area, & nice screened in back porch. Shopping malls, grocery store and pharmacies two blocks away. Take a stroll in fun Downtown Dunedin, go for a bike ride on the Pinellas Trail or play foosball and table games with the family. Short drive to Busch Gardens, Lowry Park Zoo or the Florida Aquarium. The yard is fenced in and quite spacious.

4.86 out of 5 average rating, 44 reviews

A charming single-story home is set within a well-kept yard, featuring a vibrant red brick exterior. The front porch includes seating for relaxation, while a garage accommodates a vehicle. Lush greenery surrounds the space, enhancing the inviting atmosphere.

Home in Holiday

Simply Charming

Relax with the entire family at this peaceful place to stay. This two-bedroom home is simply charming. It is perfect for a romantic getaway or a family vacation. It a front and screened in back porch area with seats for relaxing mornings and evenings. It also has a washer and dryer. Central A/C and heating. It has all new appliances. It has a workspace, 2 large screen TVs. It's pet friendly. Completely fenced in backyard. Unique decor inside. Centrally located. Easy access to Tampa & St. Pete.

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, 117 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

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.

4.99 out of 5 average rating, 143 reviews

Tropical Oasis Retreat w/ Heated Pool

Welcome to a Private oasis located in your very own backyard. Spend the day lounging by the heated pool, grill pit cooking your own food together with privacy fence. Master bed has ensuite bath. When you venture out, this Palm Harbor house is ideally located by Crystal Beach and bike ride to Honeymoon Island for some sparkling Gulf Coast beaches. With multiple golf spots like Innisbrook right next door and Clearwater beach just down the road, you can stay busy year-round. We are pet friendly

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!

Guesthouse in Town 'n' Country

4.98 out of 5 average rating, 257 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!

4.96 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

This unit private vacation rental is privately located on the property, plenty of space for 4 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Spacious living area with a kitchenette. The property is an acre of lush tropical plants Conveniently located to the downtown & beach.All our units are non-smoking and vaping.

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, 119 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, 128 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

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

A single-story home is shown, featuring a welcoming yellow exterior and a well-maintained front lawn. An American flag is displayed proudly on a pole, while a paved driveway leads to a garage. Lush greenery surrounds the property, adding to the tranquil setting.

5 out of 5 average rating, 15 reviews

Cozy Florida home

4.85 out of 5 average rating, 106 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

4.9 out of 5 average rating, 20 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

Waterfront Oasis-Tarpon Sunsets-Pool-Kayak-Fishing

4.89 out of 5 average rating, 161 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.

4.83 out of 5 average rating, 114 reviews

A serene canal setting is highlighted, featuring calm waters reflecting the surrounding greenery. Boating docks are visible along the banks, with multiple boats moored. Lush trees create a natural backdrop, while the peaceful atmosphere invites relaxation.

Home in Spring Hill

Flip Flop River Stop

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.

4.93 out of 5 average rating, 121 reviews

Lakefront home near beaches w/ waterview, pets ok

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.

5 out of 5 average rating, 13 reviews

Waterfront Gem Near Clearwater • Swim Spa + Nature

4.91 out of 5 average rating, 212 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

Pet-friendly home rentals with a pool

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, 123 reviews

Studio with Pool

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!

Guesthouse 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, 139 reviews

St Pete Casita Studio with Salt Water Pool & Yard

4.91 out of 5 average rating, 399 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!

4.84 out of 5 average rating, 175 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

4.93 out of 5 average rating, 123 reviews

Home in Largo

Swim-Out Bedroom, Waterfall pool! The Peace Place

Apartment in Clearwater Beach

An open-concept living area features a full bed, a cozy couch, and a Smart TV mounted on the wall. Natural light enters through two windows, complemented by green walls and soft curtains. A dining table with colorful chairs adds a welcoming touch to the space.

4.84 out of 5 average rating, 106 reviews

Renovated 2025 - Retro Beach Oasis with Color Pop

4.83 out of 5 average rating, 149 reviews

A modern living area features a light-colored sofa and dark accent chairs arranged around a central ottoman. A wall clock complements the artwork displayed above the couch, while the kitchen area is visible in the background, showcasing sleek cabinetry and appliances.

Condo in Paradise Lakes

Millers, BeOne Naturally Clothing Optional Premium

Private, pet-friendly home rentals

Guesthouse in Historic Kenwood

A bright living area features a white sofa and a light grey wall, creating a calm ambiance. A small kitchen area is visible with a countertop and microwave. Decorative items are arranged on open shelving, and a large mirror enhances the space. Natural light illuminates the room.

5 out of 5 average rating, 13 reviews

The Sweet Kenwood Suite

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, 74 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.

4.87 out of 5 average rating, 67 reviews

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

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

4.83 out of 5 average rating, 54 reviews

A light-filled living area features a comfortable leather sofa, a glass coffee table, and a stylish armchair. A large painting adds color to the wall, while sliding glass doors overlook greenery. A dining table with chairs is visible through the opening.

Apartment in Ozona

Waterfront 2/1 Apt in heart of Palm Harbor/Ozona

4.98 out of 5 average rating, 56 reviews

A heated salt-water pool is enclosed by a screened patio, providing a spacious area for relaxation. Comfortable lounge chairs are positioned nearby, with bright outdoor decor enhancing the inviting setting. Large glass doors open to the interior, allowing natural light to fill the space.

Home in Port Richey

Angelita's Lake Home 3br3ba w/heated pool

4.94 out of 5 average rating, 35 reviews

A cozy living area is furnished with two reclining sofas, featuring built-in cup holders. A circular lamp stands beside a small side table, and the wall is decorated with a large wall art piece and a framed decorative object. A patterned area rug covers the floor.

Home in Forest Hills

Coastal Farmhouse 2bd, fenced yard, pets welcome!