Compare Oldsmar Cottage Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Cottages in Oldsmar

Sunset Cottages Suite 1

Sunset Cottages Suite 1

Indian Shores FL
$287 nightly
The price is $320 total per night
$320 total
Jul 11 - Jul 12
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Washer
Dryer
Coastal Retreat & Biking Bliss

Coastal Retreat & Biking Bliss

Clearwater FL
This cottage is a smoke-free cottage.
Kitchen
Pet friendly
The Seaside Cottages are located just across the street from Indian Rocks Beach!

The Seaside Cottages are located just across the street from Indian Rocks Beach!

Indian Rocks Beach FL
$339 nightly
The price is $378 total per night
$378 total
Aug 4 - Aug 5
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub

Dunedin FL
$181 nightly
The price is $202 total per night
$202 total
Jul 5 - Jul 6
Total with taxes and fees
This cottage is a smoke-free cottage.
Pool
Air conditioning
Beachfront 1BR, Steps to Ocean, Dog Friendly. BOOK TODAY!

Beachfront 1BR, Steps to Ocean, Dog Friendly. BOOK TODAY!

Redington Shores FL
At this cottage, guests have access to barbecue grills.
Pet friendly
Air conditioning
Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa

Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa

Odessa FL
$226 nightly
The price is $250 total per night
$250 total
Jul 27 - Jul 28
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
The Cook Cottage sleeps 4 in Dunedin

The Cook Cottage sleeps 4 in Dunedin

Dunedin FL
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!

Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!

Clearwater FL
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
MANGO TANGO COTTAGE heated pool 2-minute walk to beach and attractions.

MANGO TANGO COTTAGE heated pool 2-minute walk to beach and attractions.

Clearwater FL
At this cottage, guests have access to an outdoor pool, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Oldsmar
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Oldsmar

    Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

    Holiday Inn Express Hotel & Suites Tampa Northwest - Oldsmar by IHG

    3990 Tampa Rd Oldsmar FL
    $100 nightly
    The price is $113 total per night from Aug 2 to Aug 3
    $113 total
    Aug 2 - Aug 3
    Total with taxes and fees
    9.4/10 Exceptional! (1,255 reviews)
    Wyndham Grand Clearwater Beach

    Wyndham Grand Clearwater Beach

    100 Coronado Drive Clearwater Beach FL
    $252 nightly
    The price is $285 total per night from Aug 2 to Aug 3
    $285 total
    Aug 2 - Aug 3
    Total with taxes and fees
    9.4/10 Exceptional! (3,465 reviews)
    Hilton Clearwater Beach Resort & Spa

    Hilton Clearwater Beach Resort & Spa

    400 Mandalay Ave Clearwater Beach FL
    $219 nightly
    The price is $248 total per night from Jul 26 to Jul 27
    $248 total
    Jul 26 - Jul 27
    Total with taxes and fees
    8.2/10 Very Good! (2,753 reviews)

Cottages

Book a cottage in Oldsmar
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Oldsmar. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Oldsmar better.

Cottage apartments in Oldsmar range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Oldsmar
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Oldsmar and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Oldsmar cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Oldsmar. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Oldsmar Cottages essential information

Accommodation
564 Cottages
Lowest Price
$113
Highest Price
$378
Popular accommodation
Sunset Cottages Suite 1, Coastal Retreat & Biking Bliss, The Seaside Cottages are located just across the street from Indian Rocks Beach!, Key West Style Cottage - with pool/hot-tub , Beachfront 1BR, Steps to Ocean, Dog Friendly. BOOK TODAY!, Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa , The Cook Cottage sleeps 4 in Dunedin, Charming Beach Cottage just steps away from Beautiful Clearwater Beach!!, MANGO TANGO COTTAGE heated pool 2-minute walk to beach and attractions.

More to Explore