
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

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.

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

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

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).

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.

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.

Private Suite with King Bed in Safety Harbor
Guest suite unit with private king bed. Located in Safety Harbor nearby downtown with close access to shops, restaurants, and more. Features a beautiful patio area to watch the sunset or sunrise with a waterfront view. The suite features high quality furniture, bedding, and appliances.
Popular amenities for outdoor seating rentals in Oldsmar
House rentals with outdoor seating

House in Oldsmar near Clearwater / Tampa Hot tub*

Hot Tub, Heated Pool, 2 Master Suites, Beach

Sunny Oasis: Villa Retreat

Palm Harbor Renovated Hideaway!

The Coastal Calm - Entire Unit

Oceanfront Escape | Private Beach | Cozy & Quiet

Cypress Place | Your Serene Retreat near Tampa!

2BR Quiet House-King Adjustable Bed-Garden-BBQ
Apartment rentals with outdoor seating

The Bohemian Studio: Separate Entry & Fenced Patio

Happy Place

Northdale Apartment

Hyde Park "Industrial-chic" with Private Backyard

2 BR, 1 bath, 2 Queen Beds, Clawfoot Tub!

Cozy Carriage House at Spring Bayou

Book Now! SALE! Cute Studio- Downtown Dunedin!

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

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

Lovely Waterview Condo/ heated pool

Tiki Themed Waterfront Condo on Tampa Bay

Bright Clearwater Condo, Heated Pool, Near Beaches

Bright and Spacious 1Bed/1Bath condo.

Amazing views on beachfront

Modern Waterfront Condo - Captivating Sunset Views

Beach Retreat #24 • Walk to Beach + Pool
When is the best time to visit Oldsmar?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €164 | €182 | €187 | €152 | €142 | €143 | €144 | €143 | €143 | €143 | €161 | €150 |
| 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 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!
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- Rentals with a patio Oldsmar
- Hotel rooms Oldsmar
- Rentals with a hot tub Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Fitness-friendly rentals Oldsmar
- Pet-friendly rentals Oldsmar
- House rentals Oldsmar
- Family-friendly rentals Oldsmar
- Waterfront rentals Oldsmar
- Rentals with a firepit Oldsmar
- Rentals with a fireplace Oldsmar
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- Rentals with beach access 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
- Anna Maria Island Beach
- Weeki Wachee Springs
- Bean Point Beach
- Coquina Beach
- Amalie Arena
- Tampa Convention Center
- Vinoy Park
- Sand Key Beach
- Dunedin Beach
- Cortez Beach
- Hard Rock Casino
- Tropicana Field
- St Pete Beach
- Anna Maria Public Beach
- Jannus Live
- River Strand Golf and Country Club
- University of South Florida
- Busch Gardens
- ZooTampa at Lowry Park
- North Beach At Fort DeSoto Park





