Search Vacation Homes in Oldsmar

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Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

Our top choices for Oldsmar vacation homes

Private kitchen
Perfect Location! All include Tampa Private Suite

Perfect Location! All include Tampa Private Suite

Perfect Location! All include Tampa Private Suite
Palm River-Clair Mel
10.0 out of 10, Exceptional, (2)
"Everything was amazing very clean accommodating safe place cozy all necessary amenities "
United States
Michelle
$101 nightly
The price is $112
Dec 19 - Dec 20
Total with taxes and fees
Perfect Location! All include Tampa Private Suite
Dining
Charming Ybor City getaway house in Tampa w/ spacious backyard

Charming Ybor City getaway house in Tampa w/ spacious backyard

Charming Ybor City getaway house in Tampa w/ spacious backyard
2.0 star property
Ybor City
9.2 out of 10, Wonderful, (15)
"An amazing price very comfortable house for four adults if I come back to Tampa, this is the place to be in"
United States
Pedro Z.
$213 nightly
The price is $239
Dec 16 - Dec 17
Total with taxes and fees
Charming Ybor City getaway house in Tampa w/ spacious backyard
Exterior
Cozy suite with separate entrance.

Cozy suite with separate entrance.

Cozy suite with separate entrance.
2.0 star property
North Park
9.6 out of 10, Exceptional, (17)
"We had a nice stay. The property was clean, and the location was perfect for exploring. The property manager was very responsive and helpful throughout our stay. The property is good for exploring the area.."
United States
Jeanne P.
$135 nightly
The price is $149
Jan 9 - Jan 10, 2026
Total with taxes and fees
Cozy suite with separate entrance.
Sun loungers, beach towels
Summer Breezes Holiday: A Charming Suite Near Florida's Best Beaches

Summer Breezes Holiday: A Charming Suite Near Florida's Best Beaches

Summer Breezes Holiday: A Charming Suite Near Florida's Best Beaches
Colonial Hills
9.6 out of 10, Exceptional, (26)
"Such a fantastic little place!! We came here for a fishing trip and this house had everything we needed. It was spotless clean and had all the amenities we could wish for (even loofahs and toothbrushes!!)We will be back!!"
United States
Malgorzata B.
$113 nightly
The price is $124
Dec 13 - Dec 14
Total with taxes and fees
Summer Breezes Holiday: A Charming Suite Near Florida's Best Beaches
A heated pool
5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub

5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub

5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub
Sun Bay South
9.2 out of 10, Wonderful, (57)
"Already sent information to host"
United States
Ria D.
$315 nightly
The price is $353
Dec 14 - Dec 15
Total with taxes and fees
5805 S Hubert Ave · Charming Tropical Pool Retreat w Hot Tub
Outdoor dining
Cozy private studio with own fenced yard-3 miles from Beach

Cozy private studio with own fenced yard-3 miles from Beach

Cozy private studio with own fenced yard-3 miles from Beach
Seminole
10.0 out of 10, Exceptional, (19)
"Easy location for family, quiet, cozy "
United States
James F.
$153 nightly
The price is $170
Dec 16 - Dec 17
Total with taxes and fees
Cozy private studio with own fenced yard-3 miles from Beach
Outdoor dining
💙Blue flower (🦋Pet friendly)

💙Blue flower (🦋Pet friendly)

💙Blue flower (🦋Pet friendly)
Largo
9.6 out of 10, Exceptional, (40)
"Everything was great. Short distance to beach. "
United States
Heather C.
$205 nightly
The price is $229
Dec 13 - Dec 14
Total with taxes and fees
💙Blue flower (🦋Pet friendly)
Fridge, microwave, oven, stovetop
Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B

Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B

Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B
University
9.4 out of 10, Exceptional, (11)
"Great rental. Very good location and amenities."
United States
Krist
$257 nightly
The price is $263
Dec 15 - Dec 16
Total with taxes and fees
Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B
Fridge, microwave, oven, stovetop
Happy Place B . Such a house

Happy Place B . Such a house

Happy Place B . Such a house
Citrus Park
9.8 out of 10, Exceptional, (34)
"We enjoyed our stay very much. "
United States
Cynthia H.
$177 nightly
The price is $198
Jan 3 - Jan 4, 2026
Total with taxes and fees
Happy Place B . Such a house
Beach
Stylish Chic King Bed Ybor DT

Stylish Chic King Bed Ybor DT

Stylish Chic King Bed Ybor DT
Ybor City
8.8 out of 10, Excellent, (15)
"Communication with the hosts was amazing. We enjoyed our stay and the house was nicely updated and decorated. Very welcoming"
United States
Nancy T.
$294 nightly
The price is $322
Dec 15 - Dec 16
Total with taxes and fees
Stylish Chic King Bed Ybor DT
Outdoor dining
The Little Pink Guest Suite

The Little Pink Guest Suite

The Little Pink Guest Suite
Tampa Heights
9.8 out of 10, Exceptional, (42)
"It was very cozy and very central to everything."
United States
Thea L.
$156 nightly
The price is $174
Dec 15 - Dec 16
Total with taxes and fees
The Little Pink Guest Suite
Outdoor dining
Water-front home with Gulf access, come stay at “El Logrado” at the Gulf

Water-front home with Gulf access, come stay at “El Logrado” at the Gulf

Water-front home with Gulf access, come stay at “El Logrado” at the Gulf
Pleasure Isles
10.0 out of 10, Exceptional, (16)
"We had a great stay, everything was in order and the host did many extras to make the stay enjoyable. This included phone chargers in the bedroom and a nice Christmas tree to keep the Christmas spirit while traveling. "
United States
Patrick V.
$266 nightly
The price is $293
Dec 15 - Dec 16
Total with taxes and fees
Water-front home with Gulf access, come stay at “El Logrado” at the Gulf
Terrace/patio
Comfy & Cozy Ybor City Studio steps from 7th Ave.

Comfy & Cozy Ybor City Studio steps from 7th Ave.

Comfy & Cozy Ybor City Studio steps from 7th Ave.
Ybor City
10.0 out of 10, Exceptional, (5)
"Cozy place to stay just a 5 minute walk to Columbia Restaurant and Centro Ybor"
Mexico
Gordon
$199 nightly
The price is $223
Dec 15 - Dec 16
Total with taxes and fees
Comfy & Cozy Ybor City Studio steps from 7th Ave.
Outdoor dining
3-bedroom villa in enchanting St. Petersburg with AC comfort

3-bedroom villa in enchanting St. Petersburg with AC comfort

3-bedroom villa in enchanting St. Petersburg with AC comfort
2.0 star property
Childs Park
$285 nightly
The price is $319
Dec 15 - Dec 16
Total with taxes and fees
3-bedroom villa in enchanting St. Petersburg with AC comfort
Terrace/patio
Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B

Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B

Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B
University
9.2 out of 10, Wonderful, (14)
"I was pleased with everything the price was great the host was very accommodating and the property was clean and as advertised "
United States
Dorrian N.
$255 nightly
The price is $261
Dec 16 - Dec 17
Total with taxes and fees
Cozy Townhome| Moffitt| Pool| Gym| Fast WiFi| 2B2B
Private kitchen
Tampa Stylish Bungalow Oasis

Tampa Stylish Bungalow Oasis

Tampa Stylish Bungalow Oasis
Tampa Heights
9.6 out of 10, Exceptional, (42)
"Everything was wonderful. Cute bungalow in a historic neighborhood"
United States
Scott B.
$229 nightly
The price is $256
Dec 15 - Dec 16
Total with taxes and fees
Tampa Stylish Bungalow Oasis
Interior
Beautiful, Quaint, and Charming 1 Bedroom Private Suite with Fenced Backyard!

Beautiful, Quaint, and Charming 1 Bedroom Private Suite with Fenced Backyard!

Beautiful, Quaint, and Charming 1 Bedroom Private Suite with Fenced Backyard!
Clearwater
8.8 out of 10, Excellent, (10)
"Amazing property with privacy and cleaniness"
United States
Shannon F.
$199 nightly
The price is $222
Dec 18 - Dec 19
Total with taxes and fees
Beautiful, Quaint, and Charming 1 Bedroom Private Suite with Fenced Backyard!
Interior
La Casita Blanca Ybor City Tampa

La Casita Blanca Ybor City Tampa

La Casita Blanca Ybor City Tampa
Ybor City
9.6 out of 10, Exceptional, (114)
"Great little place. Perfect for our weekend and conveniently located. We'll be back. "
United States
David H.
$163 nightly
The price is $182
Dec 15 - Dec 16
Total with taxes and fees
La Casita Blanca Ybor City Tampa
Terrace/patio
BBQ Games, King Beds, Private Yard

BBQ Games, King Beds, Private Yard

BBQ Games, King Beds, Private Yard
2.0 star property
Seminole
9.4 out of 10, Exceptional, (16)
"Check in was smooth and everything went well "
United States
Joe Y.
$327 nightly
The price is $365
Dec 14 - Dec 15
Total with taxes and fees
BBQ Games, King Beds, Private Yard
Terrace/patio
↳Urban 2200SF Bungalow With Stunning River View Nr. Downtown and Airport↲

↳Urban 2200SF Bungalow With Stunning River View Nr. Downtown and Airport↲

↳Urban 2200SF Bungalow With Stunning River View Nr. Downtown and Airport↲
Old Seminole Heights
9.8 out of 10, Exceptional, (36)
"Nice, spacious house. Very nice hosts. Having the Hillsborough river right outside the back door was pretty great too!"
United States
Mike W.
$238 nightly
The price is $266
Dec 14 - Dec 15
Total with taxes and fees
↳Urban 2200SF Bungalow With Stunning River View Nr. Downtown and Airport↲
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.
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Top Oldsmar Hotel Reviews

Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

10/10 Excellent
"All good"
nadia 3-night trip
Posted 21 hours ago
Hilton Clearwater Beach Resort & Spa

Find out more about Oldsmar

Oldsmar Vacation Homes information

Number of reviews
522
Accommodation
5646 Vacation Homes
Lowest Price
$112
Highest Price
$365

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