House holiday rentals in Oldsmar

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, 128 reviews

Coastal Escape: heated saltwater pool & playground

★ Close to beaches - Honeymoon Island: just 6 miles away. - Clearwater Beach: 15 miles away - crowned the nation's #1 beach Trip Advisor in 2018 ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large backyard w/ playground ★ Outdoor dining area ★ 3 bedrooms New Mattresses - California king size bed - Queen size bed - Kid-friendly room w/ two bunk beds ★ Renovated kitchen and bathrooms ★ Open living space - great for family gatherings, movie nights ★ Children toys and games

A cozy studio space features a queen size bed with a patterned blanket and bedside tables. A small armchair is situated nearby. A ceiling fan provides ventilation, and the kitchen area is visible in the background, equipped with modern appliances.

4.9 out of 5 average rating, 261 reviews

Fountain Blue Studio

Fountain blue,Great studio in the sunshine state, everything new and beautiful decorations. It’s a place for your accordance and privacy, 10 minutes away from Tampa International Airport, very close to Raymond James Stadium. Beautiful beaches and restaurants, close to everything you need. We don’t accept pets, smoking is not permited inside, we have designated area for it. Located in a safe and quit neighborhood. Description: Queen size bed, full bathroom,kitchen with with small kitchen table.

4.89 out of 5 average rating, 258 reviews

A modern kitchen area is seen with sleek cabinetry and a stylish gray sofa. The space features a silver dining table, a television mounted on the wall, and a large window revealing a private pool just outside. Fresh flowers add a touch of color.

Home in Tampa Heights

Downtown Tampa Pool House! Walk to Armature Works!

Location! Location! Enjoy Tampa at this modern brand new remodeled POOL HOUSE with the BEST LOCATION & with POOL access! SAFE & EASY location in downtown. Come Experience events, food, festivals & nightlife only 1 block from #1 destination, Armature Works- a famous destination for food, fine dining, events, & fun! Enjoy a quiet downtown getaway to enjoy the pool, biking, paddle board or walk the beautiful Riverwalk.Full kitchen! (* We had NO Damage from Hurricane and home is Not in Flood Zone).

4.7 out of 5 average rating, 108 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.

4.96 out of 5 average rating, 150 reviews

A heated saltwater pool and spa are presented, set against a serene waterfront view. Lush palm trees and well-maintained landscaping frame the area, while the tranquil canal reflects the clear blue sky. Comfortable seating is positioned nearby for relaxation.

Home in Tampa Shores

NEW Heated Salt Pool & Spa on Waterfront Canal

*****AVAILABLE TODAY - (DECEMBER 17, 2025) - BOOK NOW!!! 🏠 Welcome to this incredible, stunning & fully updated heated pool & spa home located on a serene waterfront canal of Tampa Bay! Enjoy the dock for fishing & relaxing. Fast WIFI, Samsung Smart TVs, a game room with an air hockey table, ping pong & pool table, and even a Pac-Man machine will make your stay memorable & fun! Most importantly, dive into this amazing heated pool & spa right in front of the canal!

4.94 out of 5 average rating, 235 reviews

The exterior of a two-story home is featured, set in a lush, green environment near a tranquil lagoon. Tall trees and hanging moss frame the structure, which is elevated slightly above the water. The calm water reflects the house and surrounding foliage.

Home in Tarpon Springs

Tree House Treasure

We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

4.96 out of 5 average rating, 114 reviews

A stone fire pit is surrounded by two blue chairs, positioned on a grassy area by the waterfront. Trees provide shade, and a dock is visible across the lake, complementing the serene outdoor setting.

Home in Odessa

A perfect Lake House get away

Make some memories at this unique and family-friendly slice of paradise. Located on 100-acre Lake Anne. 20 minutes from beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. Kayak, paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team

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

The living area features a spacious layout with a comfortable gray sofa and a decorative wooden coffee table. A flat-screen TV is mounted on the wall, while a well-equipped kitchen with modern fixtures is visible in the back. Natural light enters through the windows, creating a bright atmosphere.

4.98 out of 5 average rating, 122 reviews

Charming House 2B/2B Centrally Located Tampa Bay

Come and enjoy our house, 2Bedroom/2Bathroom with a clean full kitchen is the perfect place for your next vacation! This is an entire 1200sqft, AC, dryer/ washer, huge parking space, Smart TVs, internet/Wi-Fi, First AID and closet spaces. It fits up to 6 adults. This premium location offers small driving distance to restaurants and Super Walmart, is about 3 minutes to Westfield Citrus Park Mall. Busch Gardens (9 miles away).

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, 145 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

A cozy sleeping area features a spacious bed dressed in a white coverlet. Light-colored curtains frame a window, while a ceiling fan hangs above, providing airflow. A flat-screen television is mounted on the wall opposite the bed, accompanied by nightstands on either side.

4.82 out of 5 average rating, 217 reviews

Cozy, nicely situated studio!

Keep it simple at this peaceful and cozy centrically situated studio! This studio is only a 10 minute drive from Tampa International Airport and 15 minutes from International Mall, Westshore Mall and Citrus Park Mall. Additionally, it is only a 15 minute drive from downtown Tampa. You will feel peacefully at home in this private studio.

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, 140 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.

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, 184 reviews

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

A covered patio area features a built-in seating arrangement with soft cushions, accompanied by a round coffee table. The space opens to a sparkling pool surrounded by wooden decking and lush greenery, offering a serene outdoor experience.

4.99 out of 5 average rating, 123 reviews

Hacienda Hideaway w/ heated pool

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.

4.97 out of 5 average rating, 167 reviews

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

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

4.79 out of 5 average rating, 38 reviews

Home in Oldsmar

Sunny's Retreat

4.98 out of 5 average rating, 106 reviews

A serene waterfront view captures a canal lined with homes and docks. The still water reflects the soft hues of the sunset, while palm trees and boats add to the tranquil atmosphere.

Home in Bay Crest Park

Canal views, dock, Manatees, pool and more

A large screened enclosure surrounds a sparkling pool, featuring a paved patio and tropical plants. The open layout connects the pool area to a spacious kitchen and living space, providing views of the outdoors through large glass windows.

4.67 out of 5 average rating, 9 reviews

East Lake Gem On The Green

5 out of 5 average rating, 86 reviews

The Palm Haus • Heated Pool • Near Beach • Games

Weekly house rentals

A spacious sleeping area features a dark bedframe with a decorative blue and white patterned comforter. A well-equipped kitchenette is visible, showcasing modern appliances and a stylish bar area with two stools. Natural light illuminates the room, highlighting clean, neutral tones.

4.71 out of 5 average rating, 252 reviews

Tampa Bay Cozy apartment

5 out of 5 average rating, 8 reviews

Stylish Stay Near Downtown

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, 32 reviews

Beachhouse Inspired Villa Close Honeymoon Island

Lush landscaping surrounds a charming pathway leading to a white cottage. Vibrant green plants and colorful foliage are prominently featured. The patio is bordered by well-maintained mulch and manicured grass, creating an inviting outdoor space for relaxation.

4.98 out of 5 average rating, 47 reviews

Mango Tree Cottage: bike trail

The open living area features a comfortable seating arrangement with a sofa and decorative pillows. A modern kitchen is visible with stainless steel appliances, including a refrigerator and microwave. Natural light fills the space through large windows, complemented by neutral-toned cabinetry and a circular coffee table.

5 out of 5 average rating, 33 reviews

Alice House on Hillsborough River

5 out of 5 average rating, 17 reviews

The Wandering Moon

5 out of 5 average rating, 16 reviews

An open living area is shown, featuring a comfortable leather sofa and a textured area rug. The room connects to a modern kitchen equipped with stainless steel appliances and light cabinetry. Natural light is provided by window treatments, enhancing the airy feel of the space.

Home in Ozona

Ozona-All New, modern, 2 bedroom

4.78 out of 5 average rating, 9 reviews

Mama's Suite

Private house rentals

A spacious living area is furnished with a light-colored sectional sofa adorned with decorative cushions. Wall art depicting marine life adds a coastal touch, while a ceiling fan provides air circulation. A small table with a plant enhances the cozy atmosphere, complemented by natural light from the nearby window.

4.89 out of 5 average rating, 9 reviews

Clearwater peaceful retreat -new Fenced Backyard

A spacious living area is illuminated by natural light from large windows. A sectional sofa and a coffee table create a comfortable seating arrangement. A desk with chairs is positioned nearby, and potted plants add a touch of greenery to the room.

5 out of 5 average rating, 21 reviews

Executive Home | Work + Play Made Easy in Tampa

5 out of 5 average rating, 14 reviews

A welcoming facade of the house features a covered entrance with a porch, flanked by landscaped greenery. The smooth concrete pathway leads to a dark front door, and a single-car garage is visible on the right, surrounded by well-maintained grass.

Home in Barrington Hills

Coastal Calmness

An outdoor bar area is presented with a long white countertop and four high-backed stools. Decorative items are displayed on the wall above, accompanied by potted plants. A storage chest is located nearby, completing the inviting outdoor space.

4.95 out of 5 average rating, 58 reviews

Spacious 2/2 Villa w/ Air Purifier & Reading Nook

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, 74 reviews

NEW 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.

4.95 out of 5 average rating, 86 reviews

Private pool, Golf Cart, Completely Renovated!

5 out of 5 average rating, 5 reviews

Home in New Port Richey

NEW Steps to Downtown • 7 Mins to Beach + Parking

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.