
Holiday rentals with outdoor seating in Oldsmar
Find and book unique rentals with outdoor seating on Airbnb
Quick stats about holiday rentals with outdoor seating in Oldsmar

Total holiday rentals
Explore 60 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 3,160 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 40 rentals that welcome pets

Holiday rentals with a pool
40 properties feature pools

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 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!
Top-rated rentals with outdoor seating in Oldsmar
Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

Innisbrook Condo 1st Floor next to Island Course
Host is picking up the 14.1-16.5 Airnbn service fees. Innisbrook Gated Golf Resort we have a 1st floor Condo w/walk-out patio. Close to beaches with family activities, restaurants and dining. You’ll love our place because of the location, the ambiance, the neighborhood, the outdoors space, etc. *Please be advised that the amenities; pools, tennis, golf are only available to owners w/ membership and not guests of AirBnb unless a member is with you. Bars/Restaurants are open to airbnb.

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

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

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.

Cottage in Paradise.
Relax and unwind at our 2 bedroom, 1.5 bath, GUEST HOUSE (ONLY). Enjoy the pool, Beautifully landscaped grounds with Koi pond & mini golf. See birds, butterflies and more in our 1 acre botanical gardens. Free use of Golf Cart. Kayaks are available (with transport fee. I live in the main house and I'm happy to ensure that you have everything you need for an amazing vacation, while still giving you plenty of privacy. Check in & out times are not set & very flexible for your convenience.

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.

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.

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 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.

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

Tiny House Oasis - 2 Min Walk to Main Street
Experience unique tiny home living in the heart of downtown Safety Harbor! This stylish 132 sq. ft. retreat for two features soaring ceilings and a large, private outdoor oasis with a firepit and a one-of-a-kind outdoor shower. Just steps from Main Street's shops, restaurants, and the beautiful waterfront pier. Perfect for a memorable, walkable getaway.

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 outdoor seating rentals in Oldsmar
House rentals with outdoor seating

Hot Tub, Heated Pool, 2 Master Suites, Beach

BeachBunkies Cottage 1. Four miles to the beach!

Sunny Oasis: Villa Retreat

Turtle House with Private Heated Pool

Private pool, Golf Cart, Completely Renovated!

Cute Lil' House Near Historic Downtown Palm Harbor

Charming House 2B/2B Centrally Located Tampa Bay

Lakefront home near beaches w/ waterview, pets ok
Apartment rentals with outdoor seating

Waterfront studio great for Pasco scallop season!

Northdale Apartment

Cozy Apartment Overlooking Downtown Dunedin

Hyde Park "Industrial-chic" with Private Backyard

Beachy Modern Downtown Getaway I

Corner Bay Apartment

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

Dunedin Suite West, a centrally located getaway
Apartment rentals with outdoor seating

Waterfront Condo - Sunset View of Tampa Bay

Location! 1 Block from Bayshore / SOHO / Hyde Park

Bright Clearwater Condo, Heated Pool, Near Beaches

Rocky Point paradise

Amazing views on beachfront

Modern Waterfront Condo - Captivating Sunset Views

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

Upgraded 3 Bed, 3 Bath Corner Water Front Condo!
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €165 | €184 | €189 | €153 | €144 | €144 | €145 | €144 | €144 | €144 | €163 | €151 |
| 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
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Panama City Beach Holiday rentals
- Tampa Holiday rentals
- Destin Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Kissimmee Holiday rentals
- Fitness-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with pools Oldsmar
- Family-friendly rentals Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a firepit Oldsmar
- Rentals with beach access Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a patio Oldsmar
- Hotel rooms Oldsmar
- House rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with outdoor seating Pinellas County
- Rentals with outdoor seating Florida
- Rentals with outdoor seating United States
- Anna Maria Island
- Weeki Wachee Springs
- Raymond James Stadium
- Anna Maria Island Beach
- Busch Gardens Tampa Bay
- Coquina Beach
- Bean Point Beach
- Amalie Arena
- Dunedin Beach
- Vinoy Park
- Tampa Convention Center
- University of South Florida
- Hard Rock Casino
- John's Pass
- Tropicana Field
- Fort De Soto Park
- Sand Key Beach
- Anna Maria Public Beach
- Epperson Lagoon
- Weeki Wachee Springs State Park
- River Strand Golf and Country Club
- MidFlorida Credit Union Amphitheatre
- Cortez Beach
- Jannus Live





