
House vacation rentals in Oldsmar
Find and book unique houses on Airbnb
Top-rated house rentals in Oldsmar
Guests agree: these houses are highly rated for location, cleanliness, and more.

The Jungalow SOHO - Pool/Hot Tub
The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

Modern Paradise home near Clearwater Dunedin Beach
Welcome to Safety Harbor house Florida . Close to downtown main street,fun shops,restaurants ,fishing pier water front park and family friendly activities. the home sleeps 6 guests. Has a nice pool and it is great for couples ,solo adventures,business travelers,families with kids .Fully equipped brand new kitchen brand new bedrooms. Wifi TV Alexa. Tampa international airport 15 minutes Clearwater Beach 15 minutes Palm Harbor tarpon springs sunset beach 10 minutes Saint Petersburg 15 minutes.

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.

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.

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 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

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. When you book, please put the exact number of guests that are going to be staying at the property.

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

Tarpon Lake Escape LLC
Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

Private pool, Golf Cart, Completely Renovated!
Discover the ultimate retreat in a central location! Golf cart to Down town, restaurants, breweries, parks, and trails! Multiple beaches with-in a 10 minute drive. This thoughtfully equipped home is an oasis of leisure, offering a pool, games, and a fully-equipped kitchen. Optional Golf cart rentals, private boat rides and fishing trips add to the excitement. Book now for an unforgettable experience!

Happy Place
El alojamiento es un lugar muy tranquilo A menos de 5 minutos hay varios supermercados como Sprouts, Aldi , Costco Walmart Supercenter . También cuanta con una gasolinera a menos de 5 minutos, con varios restaurantes como Ford’s Garage, Outback Steakhouse, Applebee’s Grill, Chilli’s Grill, Olive Garden. Bahama Brezze y Wiskey Joe’s a 15 minutos.

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.
Popular amenities for Oldsmar house rentals
House rentals with a pool

Stunning South Tampa 6 Bedroom House

CasaBella

Private pool home near Tarpon Springs 5 mi

Sunny's Retreat

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

5 STAR! Hot Tub-freeHeated Pool 4BD/2Ba 2 King bed

Entire house in Tampa w/ Heated POOL!

Rooms with a Pool
Weekly house rentals

House in Oldsmar near Clearwater / Tampa Hot tub*

Relaxing home with palm trees & pool awaits you

Cypress Place | Your Serene Retreat near Tampa!

2BR Quiet House-King Adjustable Bed-Garden-BBQ

2 Bed 2 Bath Remodeled House Palm Harbor

Waterfront Palm Harbor Retreat w/Dock+Near Beaches

Palm & Peace Suite Private Studio in Wesley Chapel

Peaceful Hideaway
Private house rentals

The Coastal Calm - Entire Unit

Relax & Explore in a Private heated pool - hot tub

Beach Style Villa Near Dunedin & Honeymoon Island

WOW! Dunedin Coastal POOL Home-beaches-eateries

Luxury Clearwater Home • Heated Pool + Near Beach

Elegant Living: Spacious 4-Bedroom, 3-Bath Home

Open July 4! Lake Tarpon Waterfront-Private

The Shore House
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$41,828 GYD | G$44,756 GYD | G$46,220 GYD | G$37,227 GYD | G$35,135 GYD | G$34,508 GYD | G$36,599 GYD | G$36,599 GYD | G$35,135 GYD | G$38,063 GYD | G$39,736 GYD | G$38,900 GYD |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about house rentals in Oldsmar

Total vacation rentals
Explore 90 vacation rentals in Oldsmar

Nightly prices starting at
Oldsmar vacation rentals start at G$6,274 GYD per night before taxes and fees

Verified guest reviews
Over 2,910 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 50 rentals that welcome pets

Vacation rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Oldsmar vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Oldsmar rentals

4.8 Average rating
Oldsmar stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with a washer and dryer Oldsmar
- Rentals with a fire pit Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with pools Oldsmar
- Rentals with a hot tub Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with a patio Oldsmar
- Waterfront rentals Oldsmar
- Hotel rooms Oldsmar
- Rentals with outdoor seating Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with beach access Oldsmar
- House rentals Pinellas County
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- Anna Maria Island
- Raymond James Stadium
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