
Holiday rentals with outdoor seating in Oldsmar
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Oldsmar
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

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!

Bay Lake Cottage
You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

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.

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 and experience the tranquility of country living!

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.

Tiny Tulum | Tropical Oasis in Tampa’s Heart!
Welcome to Our Romantic Tulum-Inspired Retreat! Escape to a tropical paradise at our enchanting Tulum-inspired oasis, designed with romance and relaxation in mind. Nestled in a serene neighborhood, our beautifully decorated retreat offers the perfect blend of luxury, comfort, and bohemian charm, creating an idyllic getaway for couples seeking a memorable experience. Why book a generic Airbnb when you can book a hand crafted Tropical Paradise?

Cabin 1 - Marigold Moments
Discover the peaceful retreat at Cahaba Cabins, a hidden gem nestled on a working microgreen farm in Odessa. The property offers a unique blend of charm and agricultural expertise. We offer three cozy cabins where you can unwind and reconnect with nature while still being close to everything the Tampa Bay area has to offer. Each cabin offers two queen beds, a private bathroom, and a kitchenette—providing all the essentials for a relaxing stay.

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

Luxe Apartment | Water Views | Covered Balcony
Upscale, comfortable suite located within central Safety Harbor. This beautiful apartment is great for a quick getaway or a longer vacation rental. Located steps away from Bayshore Blvd which borders Tampa Bay and a 10-minute walk to Main Street Safety Harbor. Beautifully professionally designed contemporary and comfy décor. Easily walk to many restaurants, breweries, and shops!

Newly Remodeled Condo In The Heart Of Innisbrook
Newly remodeled, fully furnished second floor, one bedroom condo with 1 King bed and 1 Queen sofa. The condo has a fully equipped kitchen for your convenience and comfort. You will have access to the ("no fee")laundry room and hotel Ice maker on the same floor. Free parking is conveniently outside your building door.

Louisa's Cottage
This Cottage is located in the heart of Oldsmar. Walking distance to many of Oldsmar’s main attractions, beaches and parks 3 blocks away &Amazing variety of restaurants .This charming cottage was built in 1925 with great craftsmanship, from the wainscoting to crown mouldings .Relax and enjoy a key west Atmosphere.
Popular amenities for outdoor seating rentals in Oldsmar
House rentals with outdoor seating

Sunny Oasis: Villa Retreat

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

Wilderness Escape, by Breathtaking Natl Park

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

Gulf View on Bay: Newly Renovated

The Palm Haus • Heated Pool • Near Beach • Games

Charming House 2B/2B Centrally Located Tampa Bay

Cheerful 3-bedroom home
Apartment rentals with outdoor seating

Happy Place

Northdale Apartment

Hyde Park "Industrial-chic" with Private Backyard

Corner Bay Apartment

Private apartment perfectly located in Citrus park

Cuddle Sack near RayStadium, TPA, Busch Gar, beach

Overlooking Downtown Dunedin Two Bedroom apartment

Cozy Carriage House at Spring Bayou
Apartment rentals with outdoor seating

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Waterfront Condo - Sunset View of Tampa Bay

Perfect Location - Mins from TPA, Stadiums & Ybor

Updated Condo-Heated Pool-Private Balcony

Free Parking Pool & Water Front

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Poolside • Zero Stairs • King Bed • Near Beaches

Sunset Resort Condo – Clearwater Beaches & Bikes
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £147 | £159 | £169 | £132 | £124 | £125 | £125 | £125 | £125 | £125 | £141 | £131 |
| 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 holiday rentals with outdoor seating in Oldsmar

Total holiday rentals
Explore 70 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at £23 per night before taxes and fees

Verified guest reviews
Over 3,100 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wifi availability
70 of Oldsmar holiday rentals include wifi access

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

4.9 Average rating
Oldsmar stays are highly rated by guests – averaging 4.9 out of 5!
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- Rentals with a hot tub Oldsmar
- Fitness-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a patio Oldsmar
- Rentals with pools Oldsmar
- Family-friendly rentals Oldsmar
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- Rentals with a fireplace Oldsmar
- Hotel rooms Oldsmar
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- Rentals with a firepit Oldsmar
- Rentals with outdoor seating Pinellas County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Weeki Wachee Springs
- Coquina Beach
- Vinoy Park
- Amalie Arena
- Dunedin Beach
- Cortez Beach
- Bean Point Beach
- Anna Maria Public Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- Hard Rock Casino
- River Strand Golf and Country Club
- Tampa Convention Center
- North Beach At Fort DeSoto Park
- Busch Gardens
- Splash Harbour Water Park
- Adventure Island
- The Don CeSar
- Lakewood National Golf Club




