Search Cottages in Oldsmar

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

Compare Cottages in Oldsmar with updated reviews, rates, and availability.

30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.
Outdoor dining

30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.

9.8 out of 10, Exceptional, (174)
"This property is just steps to the beach and conveniently located. Comfortable for the 2 of us. We would love to come back."
The price is SAR 615
SAR 1,168 total
includes taxes & fees
15 Apr - 16 Apr
30 Second walk to the Beach. Newly Renovated-No Hurricane Damage. Free parking.
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Fridge, microwave, oven, stovetop

Cozy Cottage - Close to Everything, Nature Lovers Dream!

10.0 out of 10, Exceptional, (47)
"The little touches made this stay great perfect for people traveling with a dog very dog friendly"
The price is SAR 596
SAR 1,454 total
includes taxes & fees
27 Mar - 28 Mar
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Canary Beach Cottage - steps to the sand!
Aerial view

Canary Beach Cottage - steps to the sand!

9.8 out of 10, Exceptional, (38)
"This unique cottage is a comfortable base to pursue any and all vacation endeavors. Located conveniently bewtween St. Pete's and Clearwater Beach, you are either a short walk or drive to a range of restaurants and shopping opportunities. Or simply walk to the beah (only steps away) and watch the world pass by. The property manager is very attentive and will provide a nice overview of usefull tips to eliminate any stress about how to get around and where to find key resources"
Canary Beach Cottage - steps to the sand!
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Beach nearby, sun loungers, beach towels

White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

9.6 out of 10, Exceptional, (100)
"This was our 2nd time staying at the Egret cottage and we had a lovely stay. House is just as it’s pictured. Clean and comfortable. The location is great. Close to the beach yet away from the crowds."
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!
Beach towels

Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!

10.0 out of 10, Exceptional, (60)
"Very nice. Quiet we enjoyed our stay"
Riverside Casita: semi-private pool, spa, dock, garden oasis, 5 min to downtown!
Beachfront Cottages GARDEN at Beautiful Sandy Shores on Gulf of Mexico
On the beach, sun loungers, beach towels

Beachfront Cottages GARDEN at Beautiful Sandy Shores on Gulf of Mexico

10.0 out of 10, Exceptional, (165)
"We had a wonderful stay here. Everything was perfect. Clean and comfortable. Great location close to everything. "
Beachfront Cottages GARDEN at Beautiful Sandy Shores on Gulf of Mexico
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer
On the beach

Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer

8.0 out of 10, Very Good, (86)
"Clean, excellent communication with property manager! Needs a little love but the beach views can’t be beat! Highly recommend! "
The price is SAR 1,674
SAR 2,968 total
includes taxes & fees
23 Mar - 24 Mar
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer
Waterfront Cottage with a dock
Fridge, microwave, oven, stovetop

Waterfront Cottage with a dock

9.6 out of 10, Exceptional, (14)
"Property was exactly as listed. Very well decorated, provides a very intimate experience. Had such a relaxing weekend. Thank you!"
Waterfront Cottage with a dock
Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV
Interior

Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV

9.8 out of 10, Exceptional, (182)
"This is truly an amazing location. You are steps (3 minutes walking) from both the ocean and the channel, and my husband enjoyed fishing in both. There is a fishing pier on the channel and a nice heated pool. There is a wonderful restaurant with a nice outside deck and a large interior right next door, and a French pastry shop 5 minutes walk away for lunch, breakfast and coffee. We rented bikes for our full stay and did a 30 minute ride to a local park on the mainland with the Heritage...
Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Fridge, microwave, oven, stovetop

Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

10.0 out of 10, Exceptional, (127)
"Great stay and close to the sugar sand beach. Mary our host was great. I would recommend staying there."
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Island Vibes Cottage | Amazing Location
Beach nearby

Island Vibes Cottage | Amazing Location

8.8 out of 10, Excellent, (28)
"We had a great short stay in Clearwater Beach. The unit is as described, just note the front porch in the photo is not for this unit's use. Consider this a well appointed efficiency apartment, missing only an oven. Julian was very responsive to our questions... we texted and received almost immediate responses. Great for a couple retreat. "
Island Vibes Cottage | Amazing Location
Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach
A heated pool

Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach

9.6 out of 10, Exceptional, (12)
"This is my second time staying here. Very clean, well kept property. Quiet neighborhood, walking distance to beach and restaurants. "
Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach
Private family waterfront beach cottage. Best location step out to bay and gulf
On the beach

Private family waterfront beach cottage. Best location step out to bay and gulf

9.0 out of 10, Wonderful, (81)
"Loved the property and location to the beach. A short walk to restaurants in town."
The price is SAR 1,083
SAR 2,098 total
includes taxes & fees
20 Mar - 21 Mar
Private family waterfront beach cottage. Best location step out to bay and gulf
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
Beach nearby, sun loungers, beach towels

100 Steps to the Beach, Family and Pet friendly Real Beach Cottage

9.2 out of 10, Wonderful, (51)
"Great location and perfect for walking to the beach. Nothing fancy but perfect for us. My girls loved that the cottage is pink! It was nice being able to walk to dinner and shops. We had a great time!"
The price is SAR 934
SAR 2,619 total
includes taxes & fees
7 Apr - 8 Apr
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
Family Beach Apartment steps from the beach. Pet Friendly!
Outdoor dining

Family Beach Apartment steps from the beach. Pet Friendly!

8.8 out of 10, Excellent, (39)
"Was very relaxed, super close to beach and pool. Will stay again"
The price is SAR 1,459
SAR 3,049 total
includes taxes & fees
1 Apr - 2 Apr
Family Beach Apartment steps from the beach. Pet Friendly!
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
Terrace/patio

Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool

9.2 out of 10, Wonderful, (21)
"All 8 of us were impressed with the property. The management team went above and beyond to make our "
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
Cozy and roomy cottage
Outdoor pool

Cozy and roomy cottage

10.0 out of 10, Exceptional, (46)
"Peace and quiet. Units and grounds are immaculate.Lori was a joy to work with."
Cozy and roomy cottage
Cottage by the gulf
Miscellaneous

Cottage by the gulf

10.0 out of 10, Exceptional, (39)
"We enjoyed our stay on the trail near Dunedin."
Cottage by the gulf
Downtown Dunedin Cottage Near Beaches + Breweries
Beach

Downtown Dunedin Cottage Near Beaches + Breweries

10.0 out of 10, Exceptional, (51)
"Everything was perfect. Great little place with a good location."
Downtown Dunedin Cottage Near Beaches + Breweries
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Fridge, microwave, oven, stovetop

White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

9.8 out of 10, Exceptional, (134)
"Everything was good. I would rent here again. The only thing i have comment on is both bedding and all the towels were very damp/wet. We spent the first day drying everything. Not a real big issue but wasn't something i really wanted to do my firstday"
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
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.
Don't see what you're looking for?
See all available properties in Oldsmar
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Oldsmar

Chase Suite Hotel Rocky Point Tampa
Front of property

Chase Suite Hotel Rocky Point Tampa

3.0 star property
7.6 out of 10, Good, (4860)
"Super cute. We were very comfortable. There is a nice sitting area overlooking the water, a pool (we didn’t have time to use), and full kitchen in our room. Not easy to find- the sign is gone but after a couple u-turns, we made it. Check-in was easy. Bahama Breeze restaurant is a quick walk (& worth the visit!) & a little convenience store is also a quick walk. If in the area again, we would return. "
The price is SAR 578
SAR 650 total
includes taxes & fees
23 Mar - 24 Mar
Chase Suite Hotel Rocky Point Tampa
Sunset Vistas Two Bedroom Beachfront Suites
2 outdoor pools, open 9:00 AM to 10:00 PM, pool umbrellas, sun loungers

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3168)
"Great spot if you’re looking for down time at the beach, steps away from the hotel/condo. Had a renovated and clean suite. The hurricane damage can still be felt around for ex the water heaters in the pool were not yet working but the hot tubs were. Overall great stay! "
The price is SAR 1,347
SAR 1,616 total
includes taxes & fees
2 Apr - 3 Apr
Sunset Vistas Two Bedroom Beachfront Suites
Sailport Waterfront Suites
Beach nearby, beach volleyball, fishing

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very Good, (4421)
"Also peaceful and beautiful! "
The price is SAR 603
SAR 745 total
includes taxes & fees
24 Mar - 25 Mar
Sailport Waterfront Suites
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.

Frequently asked questions

Why book your cottage in Oldsmar with Expedia?
We think that a vacation should be simple, so if you’re looking for cottages in Oldsmar at an affordable rate, Expedia has you covered. Stick to the budget and select a cheap option surrounded by wilderness, or book an upscale cottage to spoil your loved ones.
How can I find cheap cottages in Oldsmar?
Expedia is here to help you track down cheap cottages in Oldsmar. To reserve your special stay in a couple of clicks, use our convenient filter tool to refine your search by star rating, budget and amenities.