Pet-friendly holiday rentals in Oldsmar

4.95 out of 5 average rating, 188 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

PetsOutdoor spacesHiking

5 out of 5 average rating, 156 reviews

A spacious living room features a large sectional sofa adorned with green pillows and a coffee table placed on a vibrant area rug with palm leaf designs. A flat-screen TV is mounted on the wall, complemented by decorative accents and artwork throughout.

Villa in Safety Harbor

Villa Key West "Villas by Christine"

Perfect location, Charming Villa Guests are loving the newly renovated Villa Key West. Christine's goal was to make guests to feel the charm of a Key West Villa while experiencing the amenities of a 5 star hotel The Living room and bedrooms have large smart TV’s with complementary Roku, Netflix, Prime and Hulu. Enjoy the view out back of one of Safety Harbors 150 year old Oak & nature pond. We are per friendly. Please let us know you will be bringing pet. Pet fee of $100.00 due upon arrival.

PetsOutdoor spacesIndoor spaces

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, 125 reviews

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!

PetsOutdoor spacesHiking

4.98 out of 5 average rating, 263 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.

PetsOutdoor spacesAccuracy

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.

4.91 out of 5 average rating, 163 reviews

Peaceful Pet friendly 2 BR cottage with hot tub.

Wellcome to our tranquil 2-bedroom, 1-bathroom farmhouse, nestled in the peaceful countryside of Palm Harbor. Whether you're seeking relaxation or adventure, this fully remodeled country cottage provides a serene and comfortable retreat. Whether you're relaxing with a movie, soaking in the hot tub, or exploring the nearby attractions, our farmhouse offers a serene and comfortable home away from home. Book your stay today! Please note that the minimum age requirement to book is 23.

WalkabilityOutdoor spacesAir conditioning

A serene backyard is featured, highlighting a sparkling pool surrounded by a spacious deck. Several lounge chairs are positioned nearby for relaxation. Lush artificial grass complements the outdoor space, while wooden fencing provides privacy.

4.71 out of 5 average rating, 112 reviews

Private Pool Home Near Clearwater & Tampa

Only 25 minutes from Clearwater Beach and Tampa, 33 minutes from Buch Gardens, 1.5 hrs from Disney, 18 minutes from Tampa International Airport. This house is completely renovated with a lot of space for you, family and/or friends. The entire house for you and your family. We have a beautiful pool with a Grill for your convinience and a garage for your car. 3 bedrooms for up to 7 persons. A 65" TV in the living room. Wi-Fi. The house has everything you need to have a relaxing time.

PetsOutdoor spacesCheck-in

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, 149 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!

Outdoor spacesPetsAmenities

4.94 out of 5 average rating, 198 reviews

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and 3 TVs for your enjoyment. The home is also conveniently located near many beaches, honeymoon island 6.9 miles Fred Howard park 11 miles ,Clearwater beach 14 miles ,Tampa and St. Pete . Please check house rules for more info. When you book, please put the exact number of guests that are going to be staying at the property.

Outdoor spacesWalkabilityParks

Guesthouse in Town 'n' Country

4.99 out of 5 average rating, 342 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!

Outdoor spacesWalkabilityIndoor spaces

The image showcases a private backyard featuring a colorful inflatable bounce house and a green putting green. An outdoor seating area is visible with a stone pathway leading to the fun play areas. The interior offers a modern kitchen and cozy lounge area, highlighted by neutral tones and contemporary furnishings.

4.77 out of 5 average rating, 100 reviews

Chic|Pool|PuttingGreen|Beaches

Enjoy a relaxing family getaway in the Sunshine State! Spend days relaxing on the beach and enjoying outdoor fun for the whole group with a bounce house, putting green, and more at this stylish home. Whether you’re traveling with family and friends or on business, this is a great place to discover the beautiful. Clearwater Beach area. 8 Min Walk to Saint George Lake 12 Min Drive to Wall Springs Park 22 Min Drive to Clearwater Beach.

PetsOutdoor spacesCondition

The illuminated pool takes center stage under the night sky, emitting a tranquil green glow. Surrounding the pool is a spacious deck, featuring lounge chairs and a table for outdoor gatherings, complemented by well-maintained landscaping in the background.

4.84 out of 5 average rating, 147 reviews

Hot Tub, Heated Pool, 2 Master Suites, Beach

Minutes from the beach is this fully renovated home with brand-new furniture. Enjoy an extra-large backyard with a hot tub, heated pool & plus a bonfire pit! Relax in the sunny Florida sunroom or park in the private double garage. Located in a quiet neighborhood, just minutes from Honeymoon Island and shopping centers. Strict no parties or events policy. Perfect for families and small groups seeking a peaceful, luxury getaway.

WalkabilityOutdoor spacesDecor

4.97 out of 5 average rating, 429 reviews

Cottage in Dunedin

Walk to Main St and Waterfront, Mins to Beaches

Experience modern coastal luxury at this designer 2-bedroom, first-floor cottage in Downtown Dunedin. Steps from Main Street and a short stroll to waterfront sunsets, shops, restaurants, and nightlife. Minutes to Honeymoon Island, Caladesi Island, and Clearwater Beach. Beautifully designed and fully stocked for families, pets, and beach days. Treat yourself to the perfect coastal getaway at Barefoot Parrot Cottages.

Outdoor spacesPetsFamily

Popular amenities for Oldsmar pet-friendly home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly house rentals

4.98 out of 5 average rating, 100 reviews

A welcoming basket sits on a light-colored countertop, filled with snacks and bottled water. A decorative sign reads 'Welcome to Our Little Piece of Paradise.' A small potted plant is positioned nearby, and the kitchen's modern appliances are visible in the background.

Home in Clearwater

Harbor Breeze Hideaway 4/2 King size bed!

WalkabilityOutdoor spacesSleep quality

An inviting living room showcases ample seating with a gray sectional couch and plush ottoman. A cozy dining area is visible outdoors, furnished with a table and chairs under a shaded canopy. The sparkling pool, surrounded by lounge chairs, is highlighted by vibrant tropical landscaping.

4.93 out of 5 average rating, 100 reviews

3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!

PetsWalkabilityBeach

4.91 out of 5 average rating, 128 reviews

Home in Clearwater

Modern Pet-Friendly Beach House w/ Heated Pool & S

Outdoor spacesPetsKitchen

4.81 out of 5 average rating, 21 reviews

Oceanfront Escape | Private Beach | Cozy & Quiet

WalkabilityOutdoor spacesBeach

4.91 out of 5 average rating, 233 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 Town 'n' Country

Rooms with a Pool

PetsOutdoor spacesHospitality

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, 15 reviews

2 Bed 2 Bath Remodeled House Palm Harbor

PetsLong stayTV

4.87 out of 5 average rating, 108 reviews

Serenity Bungalow Downtown

WalkabilityPetsKitchen

4.92 out of 5 average rating, 66 reviews

Home in Safety Harbor

Peaceful Hideaway

Outdoor spacesPetsQuiet

Pet-friendly home rentals with a pool

4.94 out of 5 average rating, 128 reviews

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

Home in Tampa

The Jungalow SOHO - Pool/Hot Tub

WalkabilityPetsFamily

4.94 out of 5 average rating, 32 reviews

A screened-in balcony area is visible, showcasing views of a large pond surrounded by lush greenery. Bright blue skies and scattered clouds reflect a serene atmosphere. Two striped chairs are positioned for relaxation, set against the tiled floor surrounded by wooden railings.

Condo in Oldsmar

Guest Favorite Waterview- 2 bed/2 bath apt w/pool

WalkabilityOutdoor spacesCondition

4.89 out of 5 average rating, 122 reviews

A ping pong table is positioned near a sparkling pool, offering a space for leisure and fun. Surrounding the pool, a spacious patio area includes several outdoor chairs and a dining table. Lush green plants provide a natural touch to the fenced backyard.

Home in Town 'n' Country

Boho Oasis • Pool •Fire Pit • Near Beach & Airport

Outdoor spacesPetsPool

An outdoor area features a heated pool surrounded by a screened enclosure, providing a bright and airy setting. Comfortable lounge chairs are positioned nearby, with greenery visible outside the enclosure. Natural light filters through the screens, creating a serene space for relaxation.

4.95 out of 5 average rating, 136 reviews

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

PetsWalkabilityLong stay

4.98 out of 5 average rating, 108 reviews

A private heated pool is surrounded by wooden decking, offering lounge chairs for relaxation. An oversized umbrella provides shade, while tropical plants enhance the outdoor space. The rear of the house is visible, along with a patio door leading into the home.

Home in St. Petersburg

ST Urban Oasis heated pool

PetsOutdoor spacesFamily

4.91 out of 5 average rating, 157 reviews

A private pool area is surrounded by lush greenery, featuring a spacious pool with a spa at one end. Sunlight reflects off the clear water, highlighting the relaxing atmosphere of the outdoor space.

Home in Tampa

Tampa Waterfront Heated Pool/ Hot Tub Oasis w Dock

PetsOutdoor spacesCheckout

4.95 out of 5 average rating, 193 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.

Apartment in Dunedin

Mermaid cottage

WalkabilityOutdoor spacesShared spaces

A spacious house is shown from the front, featuring a well-manicured lawn and a driveway leading to a two-car garage. Soft lighting highlights the entrance, with palm trees and colorful garden features enhancing the inviting exterior against a vibrant sunset sky.

5 out of 5 average rating, 13 reviews

Oldsmar fully furnished home/ pet friendly

WalkabilityOutdoor spacesAmenities

Private, pet-friendly home rentals

4.83 out of 5 average rating, 47 reviews

Casual, relaxing 2/2 SFH remodeled, in Dunedin.

Outdoor spacesWalkabilityKitchen

5 out of 5 average rating, 7 reviews

A charming outdoor space features stone pavers leading up to a cozy bungalow. Lush greenery and flowering plants surround the entrance, while two comfortable chairs with bright yellow cushions invite relaxation. Soft lighting accents the stone walls, enhancing the serene environment.

Home in Safety Harbor

"Blue Heron" Charming walkable downtown bungalow

WalkabilityLocationCleanliness

4.83 out of 5 average rating, 6 reviews

House in Oldsmar near Clearwater / Tampa Hot tub*

NearbyPoolLocation

5 out of 5 average rating, 6 reviews

Dunedin 2BR 2 bath NewBuild

HospitalityCleanlinessNearby

Guest suite in Safety Harbor

5 out of 5 average rating, 45 reviews

Suite Sunshine - An Artist's Delight

WalkabilityOutdoor spacesAmenities

5 out of 5 average rating, 10 reviews

Home in Ozona

Gulf View on Bay: Newly Renovated

WalkabilityHospitalityView

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.

4.98 out of 5 average rating, 43 reviews

Waterfront Gem Near Clearwater • Swim Spa + Nature

PetsOutdoor spacesNearby

A comfortable living area features a large sectional sofa adorned with cushions in soft tones. A textured rug anchors the space, while large windows allow natural light to fill the room, providing views of the neighborhood outside. A small coffee table sits at the center.