
House holiday rentals in Oldsmar
Find and book unique houses on Airbnb
Quick stats about house rentals in Oldsmar

Total holiday rentals
Explore 90 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $42 AUD per night before taxes and fees

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

Family-friendly holiday rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 50 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
90 of Oldsmar holiday 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!
Top-rated house rentals in Oldsmar
Guests agree: These houses are highly rated for location, cleanliness and more.

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 T and C Club
Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you won’t want to leave!

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.

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

Hot Tub, Heated Pool, 2 Master Suites, Beach
Minutes from the beach is this fully renovated home with brand-new furniture. Enjoy an extra-large backyard with a hot tub, heated pool & plus a bonfire pit! Relax in the sunny Florida sunroom or park in the private double garage. Located in a quiet neighborhood, just minutes from Honeymoon Island and shopping centers. Strict no parties or events policy. Perfect for families and small groups seeking a peaceful, luxury getaway.

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).

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

Palm Harbor/Dunedin Vacation Home w/Private Pool.
Welcome to Casa GG's! Beautifully Remodeled Home in Palm Harbor on the border of Dunedin. Close to Honeymoon Island. 2 miles from the Dunedin Causeway and a 20 minute drive to Clearwater Beach. Everything you need to feel at home. Private, resort like backyard with inground pool, outdoor seating, grill & TV. Comfortably Sleeps 8-10
Popular amenities for Oldsmar house rentals
House rentals with a pool

Turtle House: Heated Pool, 10m to Beach & Dining!

Sunny's Retreat

Dunedin 5 STAR+ Heated Pool+Near Beach

Clearwater Pool Home w/ King Bed, BBQ & Fire Pit!

Private pool, Golf Cart, Completely Renovated!

Boho Oasis • Pool •Fire Pit • Near Beach & Airport

The Palm Haus • Heated Pool • Near Beach • Games

Tropical Getaway w/Heated Pool & King Beds
Weekly house rentals

Paradise by the Park

Safety Harbor Bird House with Lake View

Nice Sparkling Clean Home with Pool.

CasaBella

Rare Spanish Retreat - Steps to Water & Downtown!

Sandcastle Cottage close to beach and trail.

Private Pool! Tropical Beaches! Palm Harbor, FL

Cozy Hen House Retreat
Private house rentals

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

Modern Cozy Home TPA, Beaches & Top Attractions

The Coastal Calm - Entire Unit

Heated Pool & Spa Oasis Near Clearwater Beach

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

Cozy Villa Close to Tampa Bay & Clearwater Beaches

MGD Lux: Near TPA, Clayman Thyroid Center.

Coastal Cottage Near Beaches w/ Golf Cart Rental!
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $271 AUD | $295 AUD | $278 AUD | $249 AUD | $235 AUD | $231 AUD | $245 AUD | $245 AUD | $235 AUD | $254 AUD | $265 AUD | $260 AUD |
| 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 |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Panama City Beach Holiday rentals
- Rentals with a hot tub Oldsmar
- Rentals with outdoor seating Oldsmar
- Rentals with pools Oldsmar
- Fitness-friendly rentals Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a patio Oldsmar
- Family-friendly rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with beach access Oldsmar
- Hotel rooms Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a fire pit Oldsmar
- House rentals Pinellas County
- House rentals Florida
- House rentals United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Bean Point Beach
- Weeki Wachee Springs
- Coquina Beach
- Anna Maria Island Beach
- Vinoy Park
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Sand Key Beach
- Tampa Convention Center
- St Pete Beach
- Hard Rock Casino
- Jannus Live
- Anna Maria Public Beach
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park
- Busch Gardens




