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Holiday homes in Oldsmar You’ll Love

Top-Rated Oldsmar Holiday homes for Every Budget and Style!

Looking for a holiday home in Oldsmar (Florida)? Browse a wide range of vacation rentals – from cozy retreats to spacious family homes – starting at just $50.00 per night. Whether you are planning a weekend getaway or a longer stay, you will find the perfect home away from home in the heart of Oldsmar.

We found 61 Holiday-homes in Oldsmar and the surrounding area (within 20 miles)

Lux gated 8 beds heated pool/jacuz, man cave in Tampa, USA

Lux gated 8 beds heated pool/jacuz, man...

Villa in Tampa near Oldsmar, Florida , 5816 Little River Drive
Lux gated 8 beds heated pool/jacuz, man cave offers accommodations in Tampa, 7.3 miles from Raymond James Stadium and 11 miles from Amalie Arena.
  • Parking
  • Swimming Pool

no reviews

from $67.00 Show details »

Welcome to Villa Marcelo in Tampa, USA

Welcome to Villa Marcelo

Villa in Tampa near Oldsmar, Florida , 8334 Fountain Avenue
Welcome to Villa Marcelo is a recently renovated villa in Tampa where guests can make the most of the garden and bar.
  • Parking
  • Bar
  • Family rooms
  • Outdoor pool
  • Swimming pool

Exceptional 8 Reviews 9.6

from $341.61 Show details »

No 1 Largest Tampa Private Compound, 11BR Sleeps 40 in Tampa, USA

No 1 Largest Tampa Private Compound, 11B...

Villa in Tampa near Oldsmar, Florida , 12310 Memorial Highway, Tampa, FL, 33635
No 1 Largest Tampa Private Compound, 11BR Sleeps 40 offers accommodations in Tampa, 10 miles from Raymond James Stadium and 14 miles from Busch Garden...
  • Pets allowed
  • Fitness centre
  • Spa and wellness centre

no reviews

from $1.018.67 Show details »

Charming Vacation House 3Be 2Ba Solar heated pool in Tampa, USA

Charming Vacation House 3Be 2Ba Solar he...

Villa in Tampa near Oldsmar, Florida , 11426 Zenith Circle
Charming Vacation House 3Be 2Ba Solar heated pool offers accommodations in Tampa, 11 miles from Raymond James Stadium and 13 miles from Busch Gardens.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Pleasant 12 Reviews 6.3

from $234.40 Show details »

CasaBella in Tampa, USA

CasaBella

Villa in Tampa near Oldsmar, Florida , 11231 Clayridge Drive
CasaBella offers accommodations in Tampa, 14 miles from Adventure Island and 14 miles from University of South Florida.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Superb 3 Reviews 9.3

from $93.00 Show details »

Family Friendly Pool Paradise Retreat Near Beaches in Palm Harbor, USA

Family Friendly Pool Paradise Retreat Ne...

Villa in Palm Harbor near Oldsmar, Florida , 1917 Spanish Oaks Drive North
Family Friendly Pool Paradise Retreat Near Beaches offers accommodations in Palm Harbor, 8.7 miles from Pier 60 and 18 miles from Raymond James Stadiu...
  • Parking
  • Pets allowed
  • Family rooms
  • Outdoor pool
  • Swimming pool

no reviews

from $460.50 Show details »

Villa Lux with pool in Palm Harbor in Palm Harbor, USA

Villa Lux with pool in Palm Harbor

Villa in Palm Harbor near Oldsmar, Florida , 2823 Oak Tree Lane
Villa Lux with pool in Palm Harbor is located in Palm Harbor, just 12 miles from Pier 60 and 18 miles from Raymond James Stadium.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming Pool

Exceptional 3 Reviews 10.0

from $67.00 Show details »

My Clearwater Crib- Beaches and Trails in every direction in Clearwater, USA

My Clearwater Crib- Beaches and Trails i...

Holiday home in Clearwater near Oldsmar, Florida , 2760 Kumquat Drive
My Clearwater Crib- Beaches and Trails in every direction offers accommodations in Clearwater, 18 miles from Chihuly Collection and 18 miles from Trop...
  • Parking
  • Pets allowed
  • Family rooms

Very good 16 Reviews 8.5

from $276.04 Show details »

Bayside Cove in Tampa, USA

Bayside Cove

Holiday home in Tampa near Oldsmar, Florida
Bayside Cove is located in Tampa, just 10 miles from Amalie Arena and 14 miles from Busch Gardens.
  • Parking
  • Pets allowed

no reviews

from $413.08 Show details »

Garden Castle in Tampa, USA

Garden Castle

Holiday home in Tampa near Oldsmar, Florida
Garden Castle offers accommodations in Tampa, 10 miles from Amalie Arena and 14 miles from Busch Gardens.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Poor 1 Reviews 3.0

from $387.37 Show details »

Delightful 3 Bdrm Home, Mins to Clearwater Beach in Clearwater, USA

Delightful 3 Bdrm Home, Mins to Clearwat...

Holiday home in Clearwater near Oldsmar, Florida , 2252 Manor Boulevard North
Providing a garden, Delightful 3 Bdrm Home, Mins to Clearwater Beach features accommodations in Clearwater.
  • Parking
  • Pets allowed
  • Family rooms

Fabulous 9 Reviews 8.6

from $353.04 Show details »

Tampa Bay Area Cottage with Gas Grill and Fire Pit! in Safety Harbor, USA

Tampa Bay Area Cottage with Gas Grill an...

Holiday home in Safety Harbor near Oldsmar, Florida
Tampa Bay Area Cottage with Gas Grill and Fire Pit! is located in Safety Harbor, just a 8-minute walk from Safety Harbor Beach and 8.6 miles from Pier...
  • Parking
  • Pets allowed
  • Fitness centre

Fabulous 1 Reviews 9.0

from $288.90 Show details »

Clearwater Home with Private Pool and Patio! in Clearwater, USA

Clearwater Home with Private Pool and Pa...

Holiday home in Clearwater near Oldsmar, Florida
Clearwater Home with Private Pool and Patio! is located in Clearwater, just 18 miles from Johns Pass and 18 miles from Johns Pass Village and Boardwal...
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Good 1 Reviews 7.0

from $61.00 Show details »

Tampa Home Near Boat Ramp about 10 Mi to Dtwn! in Tampa, USA

Tampa Home Near Boat Ramp about 10 Mi to...

Holiday home in Tampa near Oldsmar, Florida
Tampa Home Near Boat Ramp about 10 Mi to Dtwn! is located in Tampa, just 14 miles from Busch Gardens and 14 miles from Adventure Island.
  • Parking

Exceptional 2 Reviews 10.0

from $233.84 Show details »

Your Tampa Bay Vacation Entertainment Home in Tampa, USA

Your Tampa Bay Vacation Entertainment Ho...

Holiday home in Tampa near Oldsmar, Florida , 6328 Memorial Highway
Your Tampa Bay Vacation Entertainment Home is located in Tampa, just 6.7 miles from Raymond James Stadium and 11 miles from Amalie Arena.
  • Parking
  • Pets allowed

no reviews

from $212.19 Show details »

Cheerful 3 Bedroom Home mins from Clearwater Beach in Clearwater, USA

Cheerful 3 Bedroom Home mins from Clearw...

Holiday home in Clearwater near Oldsmar, Florida , 1985 Radcliffe Drive East
Cheerful 3 Bedroom Home mins from Clearwater Beach offers accommodations in Clearwater, 5.1 miles from Pier 60 and 17 miles from Johns Pass.
  • Parking
  • Pets allowed
  • Family rooms

Good 3 Reviews 7.7

from $355.90 Show details »

Getaway to iki Tampa is an End Unit Townhome - Close to Tampa Bay & Downtown - Minutes to Airport in Tampa, USA

Getaway to iki Tampa is an End Unit Town...

Holiday home in Tampa near Oldsmar, Florida , 8314 Civic Rd
Getaway to iki Tampa is an End Unit Townhome - Close to Tampa Bay & Downtown - Minutes to Airport offers accommodations in Tampa, 6.2 miles from Raymo...
  • Parking

no reviews

from $183.09 Show details »

Florida Vacation Rental with Private Pool and Hot Tub! in Safety Harbor, USA

Florida Vacation Rental with Private Poo...

Holiday home in Safety Harbor near Oldsmar, Florida
Florida Vacation Rental with Private Pool and Hot Tub! offers accommodations in Safety Harbor, 1.7 miles from Safety Harbor Beach and 7.9 miles from P...
  • Parking
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Very good 1 Reviews 8.0

from $99.00 Show details »

Quiet Waterfront Tiny Home Private Get Away in Tampa, USA

Quiet Waterfront Tiny Home Private Get A...

Holiday home in Tampa near Oldsmar, Florida , 9118 Brunswick Lane
Quiet Waterfront Tiny Home Private Get Away is located in Tampa, just 7.1 miles from Raymond James Stadium and 11 miles from Amalie Arena.
  • Parking

no reviews

from $71.00 Show details »

Perfect Escape Waterfront Oasis With Hot Tub in Tampa, USA

Perfect Escape Waterfront Oasis With Hot...

Holiday home in Tampa near Oldsmar, Florida , 9118 Brunswick Lane
Perfect Escape Waterfront Oasis With Hot Tub is located in Tampa, just 11 miles from Amalie Arena and 14 miles from Busch Gardens.
  • Parking
  • Pets allowed

no reviews

from $100.00 Show details »

Heated Pool-King Bed-Pets OK in Clearwater, USA

Heated Pool-King Bed-Pets OK

Holiday home in Clearwater near Oldsmar, Florida , 1991 Ashland Drive
Heated Pool-King Bed-Pets OK is located in Clearwater, just 5.5 miles from Pier 60 and 18 miles from Johns Pass.
  • Parking
  • Pets allowed
  • Swimming pool
  • Swimming Pool

no reviews

from $277.51 Show details »

Poolhouse in Tampa, USA

Poolhouse

Holiday home in Tampa near Oldsmar, Florida , 9105 Memorial Highway
Poolhouse offers accommodations in Tampa, 6.7 miles from Raymond James Stadium and 11 miles from Amalie Arena.
  • Parking
  • Family rooms
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

Exceptional 1 Reviews 10.0

from $365.35 Show details »

Tampas Secret in Tampa, USA

Tampas Secret

Holiday home in Tampa near Oldsmar, Florida , 5909 Mohr Road
Tampas Secret offers accommodations in Tampa, 6.9 miles from Raymond James Stadium and 11 miles from Amalie Arena.
  • Parking
  • Pets allowed
  • Outdoor pool
  • Swimming pool
  • Swimming Pool

no reviews

from $61.00 Show details »

Villa Florentina. in Clearwater, USA

Villa Florentina.

Holiday home in Clearwater near Oldsmar, Florida , 1984 Allard Drive
Featuring a garden, Villa Florentina.
  • Parking
  • Pets allowed
  • Family rooms

Superb 18 Reviews 9.2

from $304.86 Show details »

River resort, Swim spa, Adventure, Poker, Pole table in Tampa, USA

River resort, Swim spa, Adventure, Poker...

Holiday home in Tampa near Oldsmar, Florida , 5909 Mohr Rd
River resort, Swim spa, Adventure, Poker, Pole table offers accommodations in Tampa, 14 miles from Busch Gardens and 15 miles from Adventure Island. 6...
  • Parking
  • Swimming Pool

no reviews

from $89.00 Show details »

Number of Holiday homes in Oldsmar 61
Number of guest ratings 752
Average price per night $263.00
Lowest price per night $50,00
Highest price per night $7.007,40

Top 10 Cheapest Holiday-homes in Oldsmar

Discover the Cheapest Holiday-homes in Oldsmar – Ranked by Lowest Nightly Rates.

Top 10 Most Booked Holiday-homes in Oldsmar

Check out the Most Booked Holiday-homes in Oldsmar – Based on Guest Popularity.

Holiday homes in Oldsmar (Florida), comfortable and familiar

Staying in a holiday or vacation home in Oldsmar can be a great alternative to a hotel or resort. They can range from small cottages to luxurious villas, and are often located in popular tourist destinations such as beaches or mountains. One of the main benefits is the privacy and flexibility that comes with having your own space. Unlike a hotel room, a holiday home provides you with a living area, kitchen, and sometimes even outdoor space, allowing you to cook your own meals, relax in comfort, and enjoy the company of your friends or family without the interruptions of other guests.

Holiday homes often offer more space than a hotel room. This can be particularly useful for families or groups of friends traveling together, who may need more than one room or want to avoid the cramped feeling of a single hotel room. They can also provide a more authentic travel experience, allowing guests to immerse themselves in the local culture and lifestyle. This can be particularly appealing for those who prefer to stay in quieter, residential areas away from the hustle and bustle of tourist hotspots.

Find the best Holiday home in Oldsmar for your needs

Holiday homes should offer a comfortable and enjoyable stay, providing all the necessary amenities and conveniences to make your vacation experience memorable. At a minimum, your holiday home in Oldsmar should offer a clean and well-maintained living space with comfortable furnishings, adequate lighting, and climate control.

In addition to basic amenities such as a fully equipped kitchen, comfortable bedding, and clean linens and towels, holiday homes should also offer modern conveniences such as Wi-Fi, cable or streaming TV, and laundry facilities. A private outdoor space, such as a balcony or terrace, can also add to the overall enjoyment. They can also offer additional features such as a swimming pool, hot tub, or outdoor grill. Location is also important, for example, close to popular tourist attractions, restaurants and shopping areas.

Accommodation data and pictures provided by Booking.com