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, 125 reviews

Coastal Escape: heated saltwater pool & beaches

★ 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

4.9 out of 5 average rating, 253 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).

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, 122 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!

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, 144 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

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.

4.7 out of 5 average rating, 108 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.

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.

5 out of 5 average rating, 147 reviews

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, 120 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).

4.89 out of 5 average rating, 219 reviews

A modern living area showcases a sleek gray couch featuring soft tufting and a white decorative pillow. A circular wooden coffee table, supported by a geometric metal base, rests nearby, providing a casual yet stylish touch to the space.

Home in Allen's Ridge

Cute Lil' House Near Historic Downtown Palm Harbor

They say that the best things come in small packages. Well that certainly rings true in this case. Our house may be small, but it is large on personality and full of elegant charm. Newly remodeled and filled with personal touches, this small package is ready to be your Florida retreat. Enjoy charming palm harbor on our golf cart for a small rental fee.

4.79 out of 5 average rating, 161 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.

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.

4.85 out of 5 average rating, 137 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.

The outdoor space features a heated pool surrounded by a smooth concrete deck. Several lounge chairs are positioned nearby for relaxation. Lush landscaping includes palm trees, and soft lighting adds ambiance to the area, creating an inviting environment for leisure.

4.85 out of 5 average rating, 101 reviews

Modern & Spacious Retreat with Private Pool!

Welcome to our exquisite Airbnb in Oldsmar, Florida, where luxury and convenience converge in a SINGLE-story haven. This delightful getaway promises an unforgettable stay for travelers seeking relaxation, outdoor adventures, and a touch of historical charm.

A spacious studio features a comfortable bed adorned with a patterned blanket. Soft lighting is provided by bedside lamps and a floor lamp. Blue curtains frame the sliding glass door, which leads to a small outdoor seating area. A modern dresser and ceiling fan enhance the relaxing ambiance.

4.97 out of 5 average rating, 443 reviews

Private Studio-1 Exquisite space/King Bed/Near TPA

Enjoy your stay in Tampa in this cozy, newly remodeled studio! This studio is located at the center of Town and Country and is a short drive from Tampa International Airport (7 miles, which is 14 minutes away from the studio).

Popular amenities for house rentals in Oldsmar

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 26 reviews

Paradise by the Park

4.97 out of 5 average rating, 162 reviews

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.

Home in Clearwater

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

The outdoor area features a heated pool with crystal-clear water, surrounded by a screened lanai. Comfortable lounge chairs are placed nearby, providing ideal spots for relaxation. Tropical plants enhance the space, framing a serene environment perfect for swimming and sunbathing.

4.9 out of 5 average rating, 124 reviews

Heated Pool, 10 min to Beach, Close to Restaurants

A spacious pool area features a crystal-clear pool surrounded by a sun deck. Lounge chairs are set around the pool, with a screened patio providing shade. Decorative planters are placed along the perimeter, and the exterior of the house is partly visible, showcasing a light color.

4.98 out of 5 average rating, 131 reviews

Feels Like Home - 3/2 pool home that sleeps 6

A screened-in pool area features a private pool surrounded by a tiled deck, with ample space for seating and relaxation. The structure provides sun protection and is situated next to the house, blending outdoor and indoor elements.

4.82 out of 5 average rating, 111 reviews

Entire house in Tampa w/ Heated POOL!

4.88 out of 5 average rating, 8 reviews

Cozy Hen House Retreat

5 out of 5 average rating, 83 reviews

The Palm Haus • Heated Pool • Near Beach • Games

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, 4 reviews

2 Bed 2 Bath Remodeled House Palm Harbor

Weekly house rentals

4.78 out of 5 average rating, 32 reviews

Home in Dunedin

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

4.95 out of 5 average rating, 40 reviews

A serene backyard oasis is presented, featuring a circular stone patio surrounded by lush tropical plants. A cozy seating area with a fire pit is visible, along with a tall blue umbrella offering shade. The view extends to a calm waterway, bordered by trees.

Home in Ozona

Casa Del Sole

4.81 out of 5 average rating, 36 reviews

Sunny's Retreat

5 out of 5 average rating, 5 reviews

Simple pleasure. Two blocks to bay and parks.

4.94 out of 5 average rating, 65 reviews

Amazing Private Beach Home

A well-appointed bedroom features a large bed adorned with white linens and decorative pillows. A mirror and dresser are positioned nearby, complemented by soft lighting. Blue walls provide a calming backdrop for the artwork depicting trees. A nightstand with a lamp adds to the ambiance.

4.79 out of 5 average rating, 38 reviews

Charming 2 Bedroom Villa near Main Street

4.98 out of 5 average rating, 56 reviews

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.

Home in Clearwater

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

The spacious sleeping area features a large bed with patterned bedding and bedside tables equipped with lamps. A desk and chair are positioned in a corner, providing a workspace. Soft light enters through a window dressed with blinds, highlighting the warm tones of the room.

4.92 out of 5 average rating, 26 reviews

Villa Lidubina A. 3miles from TPAAirport . 1ba/1br

Private house rentals

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, 18 reviews

Executive Home | Work + Play Made Easy in Tampa

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, 57 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, 71 reviews

NEW Cozy Family Retreat, Tampa: Private Pool Oasis

4.93 out of 5 average rating, 70 reviews

Summer Escape – Pool, Downtown, Near Clearwater

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, 83 reviews

Private pool, Golf Cart, Completely Renovated!

5 out of 5 average rating, 8 reviews

Downtown | Pure Comfort | Dogs Welcome

5 out of 5 average rating, 23 reviews

An open-concept living area is shown, featuring a comfortable seating arrangement that includes a sofa and two armchairs. A dining table with chairs is visible. Large glass doors lead to a private outdoor patio, allowing natural light to fill the space.

Home in Clearwater

Townhouse in Clearwater

A modern kitchen showcases white cabinetry with stainless steel appliances and a spacious island. Soft blue backsplash tiles create a calming contrast with the countertops. Three stools are positioned at the island, and the space is illuminated by pendant lighting.