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

Total holiday rentals
Explore 100 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $43 AUD per night before taxes and fees

Verified guest reviews
Over 2,970 verified reviews to help you choose

Family-friendly holiday rentals
70 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
50 properties have a dedicated workspace

Wi-Fi availability
100 of Oldsmar holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oldsmar rentals

4.9 Average rating
Oldsmar stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Oldsmar
Guests agree: These houses are highly rated for location, cleanliness and more.

Wonderful family friendly home in Dunedin FL
Comfy Kid & Pet friendly Florida home, 15 minutes to Honeymoon Island, Caladesi 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.
4.92 out of 5 average rating, 285 reviews
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 the beautiful Gulf of Mexico beaches. Enjoy breathtaking sunsets around the fire pit. 3 Kayaks and 1 paddle board (included) or fish from the dock. Or sit and relax on the screened patio with your favorite beverage at the outdoor bar, by the fire pit, or on the dock. Or venture to beautiful downtown Tampa and enjoy the Buccaneers, Tampa Bay Lightning, or the Rays baseball team
4.96 out of 5 average rating, 135 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!
4.93 out of 5 average rating, 132 reviews
FREE Heated Pool & Spa l Book your Winter Vacation
Bring the whole family to paradise with plenty of room for fun! Enjoy a private heated saltwater pool 💦, nearby beaches 🏖️, and all the space you need in this 5-bedroom home 🏡. Enjoy amenities and games galore 🎯🎲! 📍 **Nearby Beaches:** 🌊 Crystal Beach – 10 min 🌴 Honeymoon Beach – 13 min 🌅 Sunset Beach – 20 min ☀️ Clearwater – 30 min *⚠️ Pool & spa are saltwater and heatable—pool up to 80°F, spa up to 104°F. Temps may vary due to weather.* *Maximum parking available is 5 vehicles*
4.93 out of 5 average rating, 136 reviews
Nice Sparkling Clean Home with Pool.
Spacious family-friendly retreat. Three comfortable bedrooms and a cozy sitting room within the Master Bedroom, our home offers ample space for the entire family. With two full bathrooms, everyone can enjoy their own privacy and convenience. Step outside to the inviting pool area with a spacious enclosed patio. A Fully stocked kitchen is equipped with everything for preparing and enjoying delicious meals together. Plate settings for six to a comprehensive array of utensils and pots/pans.
4.89 out of 5 average rating, 103 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.
4.73 out of 5 average rating, 117 reviews
Heated Pool 4 bed 7 miles to Honeymoon Island.
This stylish place is perfect for family vacation or work trip.. all brand new furnishing and appliances.. heated pool and 3 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.
4.94 out of 5 average rating, 202 reviews
Chic|Pool|PuttingGreen|Beaches
Enjoy a relaxing family getaway in the Sunshine State! Spend days relaxing on the beach and enjoying outdoor fun for the whole group with a bounce house, putting green, and more at this stylish home. Whether you’re traveling with family and friends or on business, this is a great place to discover the beautiful. Clearwater Beach area. 8 Min Walk to Saint George Lake 12 Min Drive to Wall Springs Park 22 Min Drive to Clearwater Beach.
4.78 out of 5 average rating, 107 reviews
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
4.98 out of 5 average rating, 116 reviews
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.
4.84 out of 5 average rating, 149 reviews
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.
4.89 out of 5 average rating, 238 reviews
BeachBunkies Cottage 1. Four miles to the beach!
No more Airbnb fees charged to guests! Welcome to the Beach Bunkies Cottages in historic Dunedin Fl. The cottages are located just 3 miles from charming downtown Dunedin, 4 miles from the stunning Honeymoon Island & Gulf coast. Both Cottages have fully accessorized kitchens and share some outside amenities. Tax will be charged and cleaning fee.
4.89 out of 5 average rating, 138 reviewsPopular amenities for Oldsmar house rentals
House rentals with a pool

Waterfront Resort with HEATED POOL!
4.93 out of 5 average rating, 152 reviews
Modern Paradise home near Clearwater Dunedin Beach
4.88 out of 5 average rating, 125 reviews
Coastal Escape: Heated Pool, Playground&Family fun
5.0 out of 5 average rating, 177 reviews
3BR Oasis | Sleeps 11 | Heated Pool | Ping Pong!
4.93 out of 5 average rating, 106 reviews
Rooms with a Pool
4.91 out of 5 average rating, 236 reviews
Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade
4.93 out of 5 average rating, 123 reviews
Entire residential home, Tampa. 3/2, Pool.
4.88 out of 5 average rating, 220 reviews
Heated Pool* 8.5 miles to Honeymoon Island. 4 bdr
4.95 out of 5 average rating, 136 reviewsWeekly house rentals

House at North Tampa 3BR & 2BA + Backyard
4.93 out of 5 average rating, 196 reviews
Steps to Downtown, Mins. to Waterfront | Sleeps 8
4.98 out of 5 average rating, 366 reviews
Sleeps 10, pet friendly/ fenced yard, near beaches
5.0 out of 5 average rating, 121 reviews
Modern Private Estate | Central to Tampa & Beaches
4.98 out of 5 average rating, 50 reviews
beautiful home oldsmar near to the beach
4.91 out of 5 average rating, 34 reviews
Sunny Oasis: Villa Retreat
4.96 out of 5 average rating, 99 reviews
Oldsmar Oasis
4.92 out of 5 average rating, 12 reviews
Cozy 3/2 residential with free parking on premises
4.81 out of 5 average rating, 89 reviewsPrivate house rentals

Palm Harbor Retreat 3/2 - Near Honeymoon Island
5.0 out of 5 average rating, 35 reviews
Luxury Clearwater Home • Heated Pool + Near Beach
4.99 out of 5 average rating, 98 reviews
Private Pool - Pickleball - Game Room - Sleeps 18!
4.7 out of 5 average rating, 20 reviews
Tropicoquette|Beach|Pool|Airport|Clearwater|STPete
5.0 out of 5 average rating, 5 reviews
Designer Home | 10 Min to Dunedin Waterfront
5.0 out of 5 average rating, 19 reviews
Backyard Oasis H/Pool, Hot Tub, Tiki Bar & Golf
5.0 out of 5 average rating, 20 reviews
Cozy Hen House Retreat
4.78 out of 5 average rating, 36 reviews
Peaceful Hideaway
4.91 out of 5 average rating, 75 reviewsWhen is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $284 AUD | $304 AUD | $314 AUD | $299 AUD | $257 AUD | $283 AUD | $249 AUD | $249 AUD | $239 AUD | $259 AUD | $270 AUD | $264 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
- Miami Holiday rentals
- Four Corners Holiday rentals
- Orlando Holiday rentals
- Kissimmee Holiday rentals
- Miami Beach Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Fort Lauderdale Holiday rentals
- Destin Holiday rentals
- Savannah Holiday rentals
- Hollywood Holiday rentals
- Jacksonville Holiday rentals
- Anna Maria Island
- Weeki Wachee Springs
- Raymond James Stadium
- Anna Maria Island Beach
- Busch Gardens Tampa Bay
- Coquina Beach
- Bean Point Beach
- Amalie Arena
- Hard Rock Casino
- University of South Florida
- Vinoy Park
- Dunedin Beach
- Epperson Lagoon
- John's Pass
- Tropicana Field
- MidFlorida Credit Union Amphitheatre
- Sand Key Beach
- Weeki Wachee Springs State Park
- Img Academy
- Anna Maria Public Beach
- River Strand Golf and Country Club
- Busch Gardens
- Cortez Beach
- Splash Harbour Water Park





