
House holiday rentals in Oldsmar
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Top-rated house rentals in Oldsmar
Guests agree: these houses are highly rated for location, cleanliness and more.

Sunny Oasis: Villa Retreat
Welcome to a stunning 2-bedroom, 2-bathroom villa nestled in the heart of sunny Florida! Whether you're seeking a relaxing beach getaway or exploring all that Florida has to offer, this villa is your perfect destination. Located 15-20 minutes from the beach in a prime location, you'll find a plethora of dining, shopping, and entertainment options nearby, ensuring there's something for everyone to enjoy. Book your stay today and experience the ultimate in comfort, convenience, and coastal charm.

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!

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.

Modern2-Story Home -Perfect for Family & Business!
This two-story house features 4 comfortable bedrooms, 3.5 bathrooms, a modern, fully equipped kitchen, and a relaxing patio with a BBQ grill—perfect for family gatherings or group getaways. Located in a peaceful and beautiful neighborhood, you’ll enjoy the quiet surroundings while being just 20 minutes from the airport and a major shopping mall, R.E. Park is just a 10-minute walk away. Whether you’re visiting for vacation or work, this home offers both comfort and convenience for your stay.

Heated Pool • Near Tarpon & Gulf Beaches 5 mi
🌴 Heated private pool oasis (Nov–Mar) 5 mi to Tarpon Springs—ideal to recharge. 🏡 Private patio for BBQ and outdoor time in a quiet area for great sleep. Perfect for families & friends: fast Wi-Fi + workspace, fully equipped kitchen, 🔑 24/7 self check-in, and 🚗 on-site parking. Easy access to Dunedin, Clearwater, Tampa, and beaches (times vary with traffic). ✨ Note: pool heat available Nov–Mar (weather permitting). ⏳ Last-minute promos active—book and lock in your dates!

Your Tampa Bay Vacation Entertainment Home
This Entertainment Oasis to Enhance Your Tampa-Bay Vacation Experience with WiFi, Pool Table & Poker-Table, Every Room has a Smart TV, USB Chargers, New AC Unit, Screen in Patio w/Pingpong Table-Dartboard-Grill, Backyard Privacy Fence. 3 BR, 2 Full Baths, 1-Air Mattress, 4-Car Driveway. Located Near Airport, RJ Stadium, International Plaza, Ben T David Beach, Clearwater Beach, Busch Gardens, & Adventure Island. Entertainment Book In The Home w/Beaches, Parks, Restaurants & Shopping.

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.

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

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

Blue Gecko Home PLUS Guest House
Welcome to Safety Harbor, site of the Hallmark feature film, Love in the Sun! Centrally located between Tampa, St. Pete and Clearwater Beach (and just an hour from Orlando!), this home is perfect for your entire family. The thoughtfully furnished main house is a fully renovated 1920’s Florida bungalow with large gourmet kitchen.
Popular amenities for house rentals in Oldsmar
House rentals with a pool

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

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Cozy Tampa Home with Large Heated Pool

Dunedin 5 STAR+ Heated Pool+Near Beach

The Palm Haus • Heated Pool • Near Beach • Games

Tropical Getaway w/Heated Pool & King Beds

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

FL Gem! XL-Pool | Pickleball | B-Ball & More!
Weekly house rentals

BeachBunkies Cottage 1. Four miles to the beach!

Farm House Tiny Home on Pinellas Trail w/ Heated P

The Coastal Calm - Entire Unit

Cozy Hen House Retreat

Luxe Private Waterfront Getaway with Pool in Ozona

FLOH - delightful days in Dunedin!

4BR Family Home • Heated Pool •Game Room

3/2 | Near Downtown | Dog Friendly | Park access
Private house rentals

Safety Harbor Bird House with Lake View

Tropical Haven: Private Pool, Hot Tub, and Bliss

Allison Palms Luxury Tampa Townhome + Pool

Private Oasis Retreat Heated Pool |Hot Tub|Beaches

Mobbly bay full

Sunset Palms Clearwater. Heated Pool. Near Beaches

Casa St.George, Centrally Located, Pool, Game Room

Angelita's Lake Home 3br3ba w/heated pool
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $247 SGD | $269 SGD | $254 SGD | $227 SGD | $214 SGD | $210 SGD | $223 SGD | $223 SGD | $214 SGD | $232 SGD | $242 SGD | $237 SGD |
| 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 holiday rentals
Explore 90 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $38 SGD per night before taxes and fees

Verified guest reviews
Over 2,860 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
50 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
90 of Oldsmar holiday rentals include wifi 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 washing machine and dryer Oldsmar
- Hotel rooms Oldsmar
- Rentals with a firepit Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Family-friendly rentals Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with beach access Oldsmar
- Rentals with pools Oldsmar
- Rentals with a patio Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with outdoor seating 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
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Dunedin Beach
- Amalie Arena
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- Tampa Palms Golf & Country Club
- ZooTampa at Lowry Park
- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Adventure Island
- Busch Gardens
- The Don CeSar
- Gulfport Beach Recreation Area
- Lakewood National Golf Club




