Search and Rent Oldsmar Condos

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4
In one month
Jan 16 - Jan 18
In two months
Feb 13 - Feb 15

Our top choices for Oldsmar condo rentals

Beach nearby, sun loungers, beach towels
SUNNY DELIGHT! pets ok! UPDATED HEATED POOL VACATION CONDO.

Condo in Seminole

SUNNY DELIGHT! pets ok! UPDATED HEATED POOL VACATION CONDO.
10.0 out of 10, Exceptional, (91)
"Superb hospitality"
Netherlands
Roy v.
$248 nightly
The price is $277
Dec 27 - Dec 28
Total with taxes and fees
SUNNY DELIGHT! pets ok! UPDATED HEATED POOL VACATION CONDO.
Beach nearby, sun loungers, beach towels
CHARMING CONDO MINUTES FROM GORGEOUS BEACHES & LOTS OF ATTRACTIONS

Condo in Clearwater

CHARMING CONDO MINUTES FROM GORGEOUS BEACHES & LOTS OF ATTRACTIONS
9.6 out of 10, Exceptional, (53)
"We had everything we needed and the condo was clean. Truly enjoyed our stay and would definitely go back again."
United States
Susan D.
$288 nightly
The price is $322
Dec 23 - Dec 24
Total with taxes and fees
CHARMING CONDO MINUTES FROM GORGEOUS BEACHES & LOTS OF ATTRACTIONS
Beach nearby, sun loungers, beach towels
UPDATED REMODELED CONDO- NO STAIRS 2 MILES TO THE BEACH! PETS ok! HEATED POOL

Condo in Seminole

UPDATED REMODELED CONDO- NO STAIRS 2 MILES TO THE BEACH! PETS ok! HEATED POOL
10.0 out of 10, Exceptional, (99)
"Lots of Fun! They think of everything you need to have a great stay."
United States
Josh
$240 nightly
The price is $278
Dec 23 - Dec 24
Total with taxes and fees
UPDATED REMODELED CONDO- NO STAIRS 2 MILES TO THE BEACH! PETS ok! HEATED POOL
Sun loungers, beach towels
PROMO PRICES- POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING

Condo in Clearwater

PROMO PRICES- POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING
9.8 out of 10, Exceptional, (46)
"Super nice. Close to pier 60 super quiet location multiple restaurants with in walking distance. Will come again."
United States
Robert
$264 nightly
The price is $295
Jan 5 - Jan 6, 2026
Total with taxes and fees
PROMO PRICES- POOL VIEW - CLEARWATER BEACH - FREE WI-FI/PARKING
Beach
Waterfront Retreat - Waves & Wellness, Serene Views

Condo in Rocky Point

Waterfront Retreat - Waves & Wellness, Serene Views
9.8 out of 10, Exceptional, (32)
"Great place to stay while in the Tampa area. Place was clean, comfortable and as advertised. The tiki bar by the pool is awesome, good food and drinks. Will definitely stay here again. "
United States
Rob L.
$209 nightly
The price is $234
Dec 23 - Dec 24
Total with taxes and fees
Waterfront Retreat - Waves & Wellness, Serene Views
Pool
Studio On The Beach - Heated Pool - Self Check-in

Condo in Belleair Beach

Studio On The Beach - Heated Pool - Self Check-in
9.0 out of 10, Wonderful, (13)
"Perfect location- just steps from the beach. Awesome shelling, tons of amazing local restaurants nearby to try. Just what we needed! "
United States
Kimberly W.
$192 nightly
The price is $214
Jan 11 - Jan 12, 2026
Total with taxes and fees
Studio On The Beach - Heated Pool - Self Check-in
Beach nearby, sun loungers
Tiki Themed Condo on Tampa Bay

Condo in Rocky Point

Tiki Themed Condo on Tampa Bay
10.0 out of 10, Exceptional, (18)
"Had a great stay in this condo. Clean and as pictured. Great views from the balcony. Would definitely stay here again. "
United States
Anonymous traveler
$200 nightly
The price is $224
Dec 26 - Dec 27
Total with taxes and fees
Tiki Themed Condo on Tampa Bay
A heated pool
Beautiful Waterfront Condo!! Amazing view!! Mins to Beach! Great location!

Condo in St. Petersburg

Beautiful Waterfront Condo!! Amazing view!! Mins to Beach! Great location!
9.8 out of 10, Exceptional, (48)
"Owner was very responsive. Convenient, clean, pretty quiet. "
United States
Edith W.
$224 nightly
The price is $250
Jan 18 - Jan 19, 2026
Total with taxes and fees
Beautiful Waterfront Condo!! Amazing view!! Mins to Beach! Great location!
Beach
Mangrove Bay - Hidden Gem, Eco Paradise

Condo in Rocky Point

Mangrove Bay - Hidden Gem, Eco Paradise
9.8 out of 10, Exceptional, (10)
"everything about this property was amazing ! "
United States
Cree
$212 nightly
The price is $236
Dec 23 - Dec 24
Total with taxes and fees
Mangrove Bay - Hidden Gem, Eco Paradise
Beach nearby
Sandy Shores 107 Side Unit on the Beach

Condo in Madeira

Sandy Shores 107 Side Unit on the Beach
8.0 out of 10, Very Good, (47)
"Situated perfectly for a fun beachy vacation! Our family loved it! Hopefully we can return in the near future. "
United States
Noelia D.
$370 nightly
The price is $412
Jan 3 - Jan 4, 2026
Total with taxes and fees
Sandy Shores 107 Side Unit on the Beach
Beach nearby
Waterfront 2/2 Condo on Treasure Island, 404E

Condo in Treasure Island

Waterfront 2/2 Condo on Treasure Island, 404E
2.5 star property
9.8 out of 10, Exceptional, (7)
"Happy to stay there anytime."
United States
Tom R.
$360 nightly
The price is $400
Jan 8 - Jan 9, 2026
Total with taxes and fees
Waterfront 2/2 Condo on Treasure Island, 404E
Sun loungers, beach towels
PROMO PRICES!!CLEARWATER BEACH 2beds,2baths,FREE WI-FI/Parking in gated comunity

Condo in Clearwater

PROMO PRICES!!CLEARWATER BEACH 2beds,2baths,FREE WI-FI/Parking in gated comunity
10.0 out of 10, Exceptional, (85)
"Beautiful stay. Nice location, clean condo. "
United States
Sami A.
PROMO PRICES!!CLEARWATER BEACH 2beds,2baths,FREE WI-FI/Parking in gated comunity
Beach nearby, sun loungers, beach towels
Cute, spacious 2 BR 2 Full BA condo minutes from the beaches

Condo in Anona

Cute, spacious 2 BR 2 Full BA condo minutes from the beaches
9.6 out of 10, Exceptional, (23)
"Great place to stay!"
United States
Deborah C.
$294 nightly
The price is $328
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cute, spacious 2 BR 2 Full BA condo minutes from the beaches
Outdoor pool, a heated pool
Condo in Gulf Waterfront Resort - Clearwater & Honeymoon Beach, Free Bikes

Condo in Dunedin

Condo in Gulf Waterfront Resort - Clearwater & Honeymoon Beach, Free Bikes
9.6 out of 10, Exceptional, (79)
"We loved our stay at this condo. Had everything we needed for my 2 kids and I. The pull out couch was comfy. We also loved having bikes to use! "
United States
Abby R.
$234 nightly
The price is $261
Dec 23 - Dec 24
Total with taxes and fees
Condo in Gulf Waterfront Resort - Clearwater & Honeymoon Beach, Free Bikes
Beach nearby, sun loungers, beach towels
SHEEK & GLAM VACATION BEACH CONDO!🌞 HEATED POOL,GYM, TENNIS, 1st FLOOR CONDO

Condo in Seminole

SHEEK & GLAM VACATION BEACH CONDO!🌞 HEATED POOL,GYM, TENNIS, 1st FLOOR CONDO
10.0 out of 10, Exceptional, (70)
"Loved our experience. Very clean & close to shops, restaurants & the beach!"
United States
Cheryl L.
$284 nightly
The price is $317
Dec 23 - Dec 24
Total with taxes and fees
SHEEK & GLAM VACATION BEACH CONDO!🌞 HEATED POOL,GYM, TENNIS, 1st FLOOR CONDO
Beach
Tropical Serenity-Water View, Heated Pool Tiki Bar

Condo in Rocky Point

Tropical Serenity-Water View, Heated Pool Tiki Bar
8.8 out of 10, Excellent, (16)
"The one bedroom Condo was packed with amenities. We loved the Tiki Bar access and the sunsets."
United States
S C.
$211 nightly
The price is $236
Dec 23 - Dec 24
Total with taxes and fees
Tropical Serenity-Water View, Heated Pool Tiki Bar
On the beach
On the Rocks! - Seaside Serenity, Wave Melodies

Condo in Rocky Point

On the Rocks! - Seaside Serenity, Wave Melodies
9.0 out of 10, Wonderful, (24)
"This was the perfect place to stay with my teen ; plenty to do and great property . "
United States
moshe k.
$221 nightly
The price is $246
Dec 23 - Dec 24
Total with taxes and fees
On the Rocks! - Seaside Serenity, Wave Melodies
Beach nearby, sun loungers, beach towels
❤Amazing Waterfront View/Near Downtown& Airport ☀🐬

Condo in Rocky Point

❤Amazing Waterfront View/Near Downtown& Airport ☀🐬
9.2 out of 10, Wonderful, (155)
"Million dollar view the place was spotless would highly recommend "
United States
Robert O.
$279 nightly
The price is $290
Dec 23 - Dec 24
Total with taxes and fees
❤Amazing Waterfront View/Near Downtown& Airport ☀🐬
Fridge, microwave, oven, stovetop
Mediterranean Apartment 5 min from the 🏝⛱🏖

Condo in Milton Park Magnolia Heights

Mediterranean Apartment 5 min from the 🏝⛱🏖
9.4 out of 10, Exceptional, (14)
"Clean and quiet stay. Just what I needed."
United States
Shaun G.
$192 nightly
The price is $214
Dec 23 - Dec 24
Total with taxes and fees
Mediterranean Apartment 5 min from the 🏝⛱🏖
Beach nearby, sun loungers, beach towels
BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS

Condo in Clearwater

BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS
9.8 out of 10, Exceptional, (116)
"Nice condo in clearwater, not too far from the beach. Decent midway point between clearwater beach and Tampa. We enjoyed our stay. The provided beach chairs and beach toys were a nice touch. "
United States
Candice B.
$301 nightly
The price is $336
Dec 25 - Dec 26
Total with taxes and fees
BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Oldsmar Hotel Reviews

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

10/10 Excellent
"Staff was amazing! Thank you!"
Joshua 3-night trip
Posted 15 hours ago
Wyndham Grand Clearwater Beach

Find out more about Oldsmar

Oldsmar Condo Rentals information

Number of reviews
1,021
Accommodation
4991 Condo Rentals
Lowest Price
$214
Highest Price
$412

Frequently asked questions

How much do condos in Oldsmar cost?
You'll pay from $214 to $412 per night for condos in Oldsmar. No matter your budget, an epic stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Oldsmar?
Oldsmar has 4991 condos. To help you book the ideal stay, make use of our filters to search for the must-have hotel conveniences.
Why book your condo in Oldsmar with Expedia?
We think that vacations shouldn't be complicated, so if you're on the lookout for condos at a competitive price, Expedia has got your back. Keep costs down and go for something small and cozy, or book a 5-star condo and spoil your favorite people. Our search filters make it simple to find an escape in Oldsmar that checks your boxes.
How can I find cheap condos in Oldsmar?
With Expedia's convenient filter tool, comparing cheap condos in Oldsmar is easy. To discover stays that'll make your wallet happy, fine-tune your search results by amenities, star rating and budget.
What is there to do in Oldsmar near my condo?
If you're eager to discover the sights of Oldsmar, check out Oldsmar Flea Market. It's a favorite among visitors and locals alike.

Explore a world of travel with Expedia