House holiday rentals in Oldsmar

4.71 out of 5 average rating, 109 reviews

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.

Home in Oldsmar

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.

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!

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.

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 and experience the tranquility of country living!

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.

4.92 out of 5 average rating, 225 reviews

Rooms with a Pool

Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.

A spacious living area is highlighted by two comfortable sofas adorned with decorative pillows. A coffee table occupies the center, while soft lighting enhances the ambiance. Large windows provide views of the outdoor area, allowing natural light to brighten the space.

4.88 out of 5 average rating, 208 reviews

The Dolphin House Clearwater. Smart TV, Cable

This 2-bedroom, 2-bathroom home is 6 miles from Clearwater Beach, voted America's #1 Beach. Local favorite downtown Dunedin is 2 miles away with shops, breweries, waterfront trails, and more. Quiet location convenient for trips to beaches, restaurants, parks, shopping, dining, and nightlife. Fully fenced yard with charcoal grill. This home has 2 washers and 2 dryers with a well equipped kitchen and screened patio, perfect for up to 8 guests.

5 out of 5 average rating, 147 reviews

The grotto-style pool area features natural rock formations with cascading waterfalls and lush tropical plants. A hot tub is integrated into the design, providing a relaxing space. The serene water reflects the clear blue sky, while views of the bay are visible in the background.

Home in Oldsmar

Bayside Retreat your tropical oasis

"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

A modern kitchen features a natural stone backsplash and light-colored cabinetry. A spacious island with dark wooden accents is surrounded by four black chairs. Built-in appliances include a white refrigerator and stacked washer and dryer. Natural light streams in through a window, enhancing the bright atmosphere.

4.94 out of 5 average rating, 124 reviews

The Fremont, Villa 2. Walk to Hyde Park!

Inspired by the French Countryside, this Villa has been designed to create a cozy but elevated experience! Just steps from Hyde Park Village, this 1 bedroom luxury private villa was built specifically for Airbnb and just completed in March of 2024. Custom finishes and curated design make for an exceptional place to stay in the most desirable area of Tampa. Traveling for a few nights or a few months this unit has it all!

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

Welcome to your private backyard oasis. Relax by the heated pool, grill and dine outdoors, all within a fenced-in space. This home is ideally located—just a short drive to Crystal Beach, minutes from downtown Palm harbor, Dunedin and Tarpon Springs, and bike ride away to Pinellas Trail, golf courses, Honeymoon Island, and Clearwater Beach. Pets are welcome

4.79 out of 5 average rating, 163 reviews

Home in Tarpon Springs

Mins to Beach/Studio Home/walk to dwtn/FreeParking

✨ Beautifully remodeled studio in the heart of Tarpon Springs. Just an 8-minute drive to the beach, this cozy retreat was thoughtfully designed with comfort in mind. Featuring a comfy queen bed and a bright, welcoming interior, it’s the perfect spot to relax after exploring the Sponge Docks, downtown, and nearby attractions.

Home in Timberlane Woodlake

A hot tub is set on a wooden deck surrounded by bar stools, with views of a lush backyard and a serene lake beyond. Tall palm trees frame the scene, while the sky displays soft clouds and warm lighting.

4.96 out of 5 average rating, 314 reviews

The perfect lake house getaway near the airport.

Relax with the whole family in this cozy residence in the Tampa Bay area. Enjoy the spacious backyard and unwind in the hot tub with peaceful views of the lake. Set in a centric location near the International Airport, Raymond James Stadium, Busch Gardens, Adventure Island, Citrus Park mall and Florida's best-rated beaches.

A work area is positioned near a window, featuring a sleek desk and an adjustable white chair. Light gray curtains frame the window, allowing for natural light. A small lamp and decorative item are placed on the desk, contributing to the space's functional design.

4.86 out of 5 average rating, 143 reviews

My Little White Space .

My apartment is located an excellent position of access to different places of Tampa bay .Apartment with independent entrance.Near to: Tampa international airport-4miles Mall international plaza-4 miles Downtown Tampa 8.7 miles Raymond James stadium Beaches within 5 miles. NO CHILDREN OR PETS WILL BE ADMITTED.

4.89 out of 5 average rating, 121 reviews

A charming cottage exterior is framed by lush greenery and palm trees, with a welcoming blue front door. A stone pathway leads to the entrance, surrounded by an inviting garden. The cottage is nestled within a fenced yard, providing a sense of privacy.

Home in Dunedin

BeachBunkies Cottage 1. Four miles to the beach!

Welcome to the Beach Bunkies Cottages in historic Dunedin Fl. The cottages are located just 3 miles from charming downtown Dunedin, 4 miles from the stunning Honeymoon Island & Gulf coast. Both Cottages have fully accessorized kitchens and share some outside amenities.

Popular amenities for Oldsmar house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.95 out of 5 average rating, 104 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 Palma Ceia

The Jungalow SOHO - Pool/Hot Tub

A serene outdoor space features a rectangular swimming pool, surrounded by a spacious paved area. Two chairs are positioned near the pool. A white fence provides privacy, while trees line the background, enhancing the tranquil setting.

4.8 out of 5 average rating, 119 reviews

Villa Paradise

A heated swimming pool is surrounded by a covered patio. A dark wicker seating area is visible next to the pool, along with a grill and an outdoor projector displaying an image on a wall. String lights create a soft illumination around the space.

4.94 out of 5 average rating, 139 reviews

Cozy Tampa Home with Large Heated Pool

4.83 out of 5 average rating, 215 reviews

Spacious home / 35 Foot Pool/Patio on park 10% off

A screened-in private pool surrounded by a spacious deck is visible, featuring colorful floatation rings resting on the water. Comfortable seating areas are arranged nearby, with overhead lighting softly illuminating the space. Lush greenery can be seen in the background, enhancing the serene atmosphere.

4.95 out of 5 average rating, 159 reviews

Tropical Getaway w/Heated Pool & King Beds

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

5 out of 5 average rating, 133 reviews

Coastal Escape: heated saltwater pool & playground

The kitchen features wooden cabinetry, a central island with seating, and modern appliances. Natural light enters through the glass doors, illuminating the granite countertops. A coffee maker and dishwasher are visible, and the tiled floor adds a polished finish to the overall space.

4.87 out of 5 average rating, 192 reviews

Entire residential home, Tampa. 3/2, Pool.

The outdoor area showcases a saltwater pool within a screened lanai, surrounded by a patio area with seating. The pool area is illuminated by natural light, enhancing the space's openness. A game room features plush seating arranged for viewing films, with walls designed for a cinematic experience.

4.93 out of 5 average rating, 163 reviews

Clearwater Gameroom- Pool/Mini golf/Home Theatre

Weekly house rentals

A selection of woven storage baskets is displayed on a countertop, featuring neatly arranged napkins and two water bottles. A decorative sign reading 'HOME SWEET HOME' adds a personal touch to the arrangement, blending function with a welcoming aesthetic.

5 out of 5 average rating, 24 reviews

Palm Harbor Renovated Hideaway!

A corner duplex villa is seen with a two-car garage and a welcoming entrance. Mature trees provide shade over the driveway, and a landscaped front yard features greenery along the home’s facade, creating a serene atmosphere.

4.91 out of 5 average rating, 33 reviews

Beachhouse Inspired Villa Close Honeymoon Island

4.87 out of 5 average rating, 70 reviews

Valencia Manor, your Favorite Florida Pool Home!

4.94 out of 5 average rating, 18 reviews

AeroLuz Your modern refuge.

The exterior entrance features a welcoming porch with two dark chairs positioned around a small table. Colorful flowers and plants are arranged in the landscaped area, complemented by white gravel and decorative pots, enhancing the outdoor appeal.

4.91 out of 5 average rating, 54 reviews

HSE Bush Garden 20min/Tesla EV/15 min from Airport

4.93 out of 5 average rating, 69 reviews

Home in Oldsmar

Amazing Private Beach Home

A recreational space features a red felt pool table with colorful balls arranged on the surface. In the background, modern laundry appliances are positioned beside a vibrant wall with geometric designs and nautical motifs, creating a fun atmosphere for leisure activities.

4.98 out of 5 average rating, 59 reviews

Casa Sea Belkis/Beach/Jacuzzi/Golf/BBQ/Games

4.92 out of 5 average rating, 51 reviews

Home in Safety Harbor

Peaceful Hideaway

Private house rentals

4.8 out of 5 average rating, 40 reviews

Home in Dunedin

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

A spacious living area features a large grey sectional sofa adorned with orange and blue accent pillows. A marble coffee table sits in front, while a ceiling fan is visible above. Light enters through large windows, illuminating the open layout connecting to a dining area.

4.97 out of 5 average rating, 34 reviews

The Coastal Calm - Entire Unit

A vibrant outdoor oasis features a cozy plunge pool surrounded by sun loungers. A shaded seating area includes a table with four chairs. The space is enhanced by decorative elements, including a pergola with hanging egg chairs, all set against a lush green lawn.

4.96 out of 5 average rating, 78 reviews

Cozy Family Retreat, Tampa: Private Pool Oasis

An outdoor area features a private pool surrounded by a concrete deck. Lounge chairs and a dining table are visible beneath a covered patio, while tropical landscaping adds greenery. A path of stepping stones leads toward the pool, inviting relaxation and leisure.

4.96 out of 5 average rating, 89 reviews

Private pool, Golf Cart, Completely Renovated!

A stylish living area features a light-toned wooden table with a decorative tray holding a bottle with a nautical design, a small plant, and a piece of coral. A cozy sofa and a dining table set for four are visible in the background, complemented by neutral walls.

4.91 out of 5 average rating, 54 reviews

BlueJay's Nest: private retreat w/ yard and patio

5 out of 5 average rating, 93 reviews

The Palm Haus • Heated Pool • Near Beach • Games

5 out of 5 average rating, 40 reviews

The kitchen area showcases modern cabinetry and a sleek granite countertop, illuminated by natural light from large, nearby windows. A partial view of the pool can be seen through the screen-enclosed patio, highlighting the seamless indoor-outdoor connection.

Home in Allen's Ridge

Private Coastal Getaway to Connect and Celebrate

Superhost

The kitchen area features modern cabinetry and stainless steel appliances, including a refrigerator, microwave, and stove. A small desk with a chair is positioned near the window, allowing natural light to illuminate the space. The wood-like flooring adds warmth to the room.