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House vacation rentals in Oldsmar

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Top-rated house rentals in Oldsmar

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Top guest favorite

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

4.91 out of 5 average rating, 267 reviews

Wonderful family friendly home in Dunedin FL

Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caledesi 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.

Top guest favorite

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.

Home in Palm Harbor

5 out of 5 average rating, 119 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

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

4.91 out of 5 average rating, 243 reviews

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).

Top guest favorite

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.

Home in Palm Harbor

4.92 out of 5 average rating, 119 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!

The cabin is viewed from the water, featuring a stylish exterior and a spacious deck. A newly constructed dock extends over the calm canal waters, surrounded by lush greenery. A clear blue sky enhances the inviting natural setting.

4.77 out of 5 average rating, 266 reviews

*Waterfront* Kayaks & Bikes - Papa’s Rustic Cabin

Experience True Old Florida! Papa’s Cozy, Rustic, Oceanfront Cabin. One of the last true Old Florida neighborhoods in the area. Located near charming Oldsmar. This is a Saltwater Gulf canal, only a few houses down from open the open Gulf in Tampa Bay. Great for the outdoorsy vacationer. Brand new dock. 2 kayaks (individual rider) & 2 bicycles provided. Depth of the canal moves up and down with the tides. It’s usually shallow but has many fish in high tide. Central location to Tampa & beaches!

Top guest favorite

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.

Home in Palm Harbor

4.99 out of 5 average rating, 141 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.

Home in Oldsmar

4.7 out of 5 average rating, 105 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.

A welcoming living room features a dark front door, a light-colored wall, and natural wood flooring. A green sectional couch and a round orange ottoman provide seating options. A small plant is situated next to the couch, and a framed piece of artwork adorns the wall.

4.92 out of 5 average rating, 127 reviews

Historic 2BR Bungalow, 7 Min TPA

This two-bedroom one-bath bungalow showcases the timeless architecture of Old West Tampa artfully brought into the 21st century with vintage charm and modern flair. Pet-friendly with fully enclosed fence. Centrally located near the airport and between Westshore and Downtown Tampa, this cozy, super clean home is a great place to return to after a long day of exploring Tampa Bay, or the perfect getaway if you just want to escape it all in this historic west Tampa neighborhood.

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

4.94 out of 5 average rating, 232 reviews

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.

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, 220 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.

Top guest favorite

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

5 out of 5 average rating, 145 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

An open-concept living space features a blend of seating options, including two patterned armchairs and a plush blue sofa. A round coffee table is centrally positioned on a textured area rug. The kitchen area includes modern appliances and bar stools around a kitchen island.

Home in Palm Harbor

4.96 out of 5 average rating, 174 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 three 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.

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Popular amenities for Oldsmar house rentals

Free parking on premises

Air conditioning

House rentals with a pool

Top guest favorite

A spacious covered screened porch features a heated pool visible nearby. Lounge chairs with cushions are arranged beside the pool. A dining table with chairs is positioned on the porch, alongside a propane gas grill, all set against a backdrop of surrounding greenery.

Home in Port Richey

4.99 out of 5 average rating, 248 reviews

Heated & Screened in Pool-All Essentials Provided

A spacious outdoor area features a large checkers and chess board on a checkered surface, surrounded by vibrant green artificial grass. A pool area is visible in the background, with a privacy fence and sunlit space for leisure activities.

Home in Pinellas Park

4.98 out of 5 average rating, 140 reviews

Insta Worthy Retreat - Heated pool-putt putt | Bar

A private swimming pool is surrounded by a screened patio, with colorful floatation devices resting on the clear water. Lounge chairs are positioned nearby against a bright yellow wall. Natural light floods the area through glass doors, creating a refreshing atmosphere.

Home in Forest Hills

4.9 out of 5 average rating, 113 reviews

Pool Getaway · Near Tarpon Springs & Beaches. 5 mi

Top guest favorite

A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.

Home in Tarpon Springs

4.96 out of 5 average rating, 370 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

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.

Home in Palm Harbor

4.95 out of 5 average rating, 158 reviews

Tropical Getaway w/Heated Pool & King Beds

Top guest favorite

A playground structure is shown with a slide and a small platform, set on green grass. Beyond the playground, a screened-in pool area is visible, with water reflecting the surrounding trees and sky. The tranquil backyard environment offers space for relaxation.

4.98 out of 5 average rating, 172 reviews

Tropical Getaway, Perfect Home & Great Location

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.

Home in Palm Harbor

4.94 out of 5 average rating, 124 reviews

Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr

Top guest favorite

The kitchen features wooden cabinetry with glass fronts, complemented by countertops and tiled backsplash. A large island with seating is visible, alongside modern appliances. The adjoining dining area is seen through expansive windows, providing a view of the outdoor space, brightened by natural light.

Home in Clearwater

4.88 out of 5 average rating, 120 reviews

3 BR/2B pool home WiFI and Brand new furnishings

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.

4.7 out of 5 average rating, 240 reviews

Tampa Bay Cozy apartment

A cozy sleeping area features a soft pink quilt on a spacious bed, complemented by two decorative pillows. Nightstands with lamps are positioned on either side, and framed artwork is displayed above the bed. The light grey walls and marble flooring contribute to a serene environment.

4.81 out of 5 average rating, 21 reviews

El paraíso

Top guest favorite

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.

Home in Palm Harbor

5 out of 5 average rating, 18 reviews

Palm Harbor Renovated Hideaway!

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.

Home in Palm Harbor

4.97 out of 5 average rating, 32 reviews

The Coastal Calm - Entire Unit

Top guest favorite

A spacious backyard features a heated pool surrounded by lounge chairs and colorful inflatable swans. A putting green is visible, along with several outdoor seating options. The cozy firepit area invites relaxation, complemented by illuminated string lights creating a welcoming ambiance.

Home in Dunedin

4.95 out of 5 average rating, 62 reviews

Sea Breeze Haven~Htd Pool ~ NFL~FirePit ~PuttPutt

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.

Home in Palm Harbor

5 out of 5 average rating, 4 reviews

2 Bed 2 Bath Remodeled House Palm Harbor

Home in Palm Harbor

4.75 out of 5 average rating, 4 reviews

Mama’s Suite

The exterior view of the home reveals a spacious backyard, framed by lush green grass and shaded by trees. A screened-in pool area is visible, providing a safe and inviting space for relaxation and recreation.

Home in Oldsmar

5 out of 5 average rating, 6 reviews

Shore Drive Sunshine

Private house rentals

Top guest favorite

A modern living room is featured, showcasing a dark sectional sofa complemented by decorative pillows. Large windows are adorned with sheer curtains, allowing natural light to illuminate the space. A round coffee table sits at the center, decorated with a floral arrangement and magazines. A mirror reflects the inviting atmosphere.

5 out of 5 average rating, 19 reviews

Gretel Paradise Suite

A modern single-story house is set on a manicured lawn, featuring a paved driveway and a two-car garage. In front, two colorful chairs are positioned under the shade of mature trees, enhancing the welcoming entrance of the home.

Home in Palm Harbor

4.79 out of 5 average rating, 34 reviews

Newly Remodeled*3 Beds*Pool*Game Room*10minBeach

A spacious backyard features a deck with colorful lounge chairs arranged for relaxation. A barbecue grill is positioned nearby, alongside a cooler and fishing gear. A kayak is available, and lush trees provide a natural backdrop, enhancing the outdoor setting.

4.93 out of 5 average rating, 29 reviews

Kayak and Fishing Waterside Retreat

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.

Home in Palm Harbor

4.67 out of 5 average rating, 9 reviews

East Lake Gem On The Green

Top guest favorite

A cozy living area showcases a vibrant green couch paired with a wooden coffee table. A wall of bookshelves filled with colorful books serves as a backdrop, while decorative items are placed on a shelf above. Bright patterned area rugs and light from the window enhance the space.

Home in Palm Harbor

4.98 out of 5 average rating, 48 reviews

Hatties Hill Florida

The spacious living room is furnished with a light grey sofa and a pullout couch, accompanied by a modern coffee table. Natural light is welcomed through multiple windows, while a ceiling fan adds comfort. Artwork adorns the walls, creating an inviting ambiance.

Home in Palm Harbor

5 out of 5 average rating, 12 reviews

The Retreat at Palm Harbor - RV & Work-Friendly

A modern living area is presented with light wood flooring and large windows allowing natural light. A round coffee table is centered among a plush sofa and a curved armchair. Greenery is visible from the window, adding a touch of nature to the interior.

Home in Bay Crest Park

4.96 out of 5 average rating, 46 reviews

3BR Waterfront House I Raymond James Stadium

Top guest favorite

An outdoor seating area is surrounded by vibrant trees and a white privacy wall. Blue armchairs and a small table are situated on a paved patio, offering a comfortable spot to relax. The screened-in pool area is visible in the background, complemented by a well-maintained backyard.

Home in Palm Harbor

5 out of 5 average rating, 43 reviews

Beautiful house with pool, fire pit, billiard room

Quick stats about house rentals in Oldsmar

Total rentals
80 properties
Nightly prices starting at
€ 26 before taxes and fees
Total number of reviews
2.8K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
40 properties have a pool

Destinations to explore