Oldsmar Vacation Rentals

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Browse Select Oldsmar Vacation Homes

House with unique style 3/2 Near Raymond Stadium
9.4 out of 10, Exceptional, (21)
"This home is nice to fit 3 people. The beds are not very comfortable and they are only full sized which makes it hard to sleep. The pillows are also hard. Not enough towels for the size of house. One towel each! The vent in the master bathroom is full of dust and stuff is hanging out of it. The towel bar and shower bar fell off. The grass was over a foot tall and so there were lots of bugs and a few lizards (which Tampa has but it would be nice if the property was taken care of). The TV doesn’t...
The price is CA $298
CA $539 total
includes taxes & fees
Nov 7 - Nov 8
House with unique style 3/2 Near Raymond Stadium
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
10.0 out of 10, Exceptional, (241)
"My husband and I stayed in this condo days after Hurricane Milton swept through the area. We had really good communication with the owner in the days leading up to the trip, and he graciously let us adjust our dates so we could still have our anniversary trip. We did not get the full Clearwater Beach and Resort experience because so many businesses were still closed from hurricane damage, but we really enjoyed the quiet beach and the sunsets. The resort staff was very friendly and had great...
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa
* Cozy Beach House * Look No Further *
10.0 out of 10, Exceptional, (136)
"It was good"
The price is CA $277
CA $676 total
includes taxes & fees
Nov 7 - Nov 8
* Cozy Beach House * Look No Further *
Private entrance room & bathroom w/ courtyard 10 min to beach & Downtown
10.0 out of 10, Exceptional, (29)
"Stayed here while I was working after the hurricanes. Very kind and friendly host! The place is cozy and in a great location. ❤️"
The price is CA $98
CA $186 total
includes taxes & fees
Nov 17 - Nov 18
Private entrance room & bathroom w/ courtyard 10 min to beach & Downtown
Steps to a Private Beach Perfect Family Vacation
10.0 out of 10, Exceptional, (97)
"Trip was for my 50th Bday and my sons 21st. It was us and both of our best friends. House was amazing! Even more beautiful in person. Just a few steps on your on the beach. Sitting out on the back patio, listening to the sound of the waves was priceless and so relaxing. We felt right at home. George goes above and beyond making sure you have an amazing experience. Everything you need is there. Would definitely recommend and we will definitely be back!!"
Steps to a Private Beach Perfect Family Vacation
Rockin' home near Hard Rock, Fairgrounds, and MidFlorida Amphitheater.
9.8 out of 10, Exceptional, (34)
"The property was super cute. There were 4 of us and a baby, and it was 3 bedrooms and plenty of room for us all. The host was absolutely great at communication. Would 100% stay again next time we are in town."
The price is CA $160
CA $384 total
includes taxes & fees
Nov 11 - Nov 12
Rockin' home near Hard Rock, Fairgrounds, and MidFlorida Amphitheater.
Tampa's Paradise
9.8 out of 10, Exceptional, (7)
"Overall, we had a great vacation. Communication with owner was excellent! Place was a little smaller than appeared on listing but still plenty of room for our large, adult family. Pool was a great place to hang out and make memories! Blackstone was provided and was surprisingly clean and ready to use which pleased my husband, lol. Location to Busch Gardens, beaches, etc was perfect. However, there were multiple things which dampened the fun. I had to clean when we first arrived. The floors were...
The price is CA $452
CA $1,108 total
includes taxes & fees
Nov 7 - Nov 8
Tampa's Paradise
The Great Escape 3BR 2B Entire house
10.0 out of 10, Exceptional, (74)
"Great location and lots to do around. The hot tub was perfect. Everything we needed was provided along with extra. We even used the beach supplies which came in very handy. This house is cozy and comfortable! Thanks Mike and Paige "
The Great Escape 3BR 2B Entire house
8 minutes from the AIRPORT~ New SaL POOL - WiFi 1gbps/free Parking... BBQ
9.8 out of 10, Exceptional, (42)
"Nice house and pool. I do believe someone lives in the garage but I only saw them once (maybe a traveling nurse) when she was entering her place. There is no entry from the home to the garage/property where the other person was staying"
8 minutes from the AIRPORT~ New SaL POOL - WiFi 1gbps/free Parking... BBQ
Cozy Home in Heart of Tampa w/ Lanai & Pool!
10.0 out of 10, Exceptional, (36)
"We were a group of ladies attending a conference at Amalie Arena. We needed a place to stay that would accommodate all of us and within our budget. This house suited our needs well. The neighborhood is fine, but not resort like - it definitely feels residential. It has a good amount of space so families or groups have room to spread out. We didn't spend a lot of time at the house as we were gone from morning to night. A few things to point out - the bunk beds, as well as the main floor...
Cozy Home in Heart of Tampa w/ Lanai & Pool!
☀Shelley Casa, 3BR/2BA,Stunning- ✔Pool✔WHOLE HOUSE
8.2 out of 10, Very good, (33)
"This house meet ever expectation! I can't wait to stay again. Area beautiful, home gorgeous everything we needed. Loved staying here and can't wait to stay again!"
The price is CA $143
CA $430 total
includes taxes & fees
Nov 11 - Nov 12
☀Shelley Casa, 3BR/2BA,Stunning- ✔Pool✔WHOLE HOUSE
Cozy private 1 bedroom & bath Suite in the "Sunshine City" min's to beaches/city
9.6 out of 10, Exceptional, (85)
"Cozy, Clean, canvas covered patio. I’ve stayed at this property many times. "
Cozy private 1 bedroom & bath Suite in the "Sunshine City" min's to beaches/city
Family-Friendly Tampa Home < 3 Mi to Ocean!
9.8 out of 10, Exceptional, (26)
"This residence has become a mainstay for my company when we come to Tampa for business when only a couple of us come down. Better than a hotel. "
Family-Friendly Tampa Home < 3 Mi to Ocean!
Modern Pool House Oasis
10.0 out of 10, Exceptional, (42)
"Beautiful home with a great pool. Our trip was cut very short due to Hurricane Milton. "
Modern Pool House Oasis
making memories at madeira
9.6 out of 10, Exceptional, (8)
"The house is very clean and stocked with everything needed. The host was very responsive, friendly and kind. One of the best experience I ever had renting a house. "
making memories at madeira
Tampa Villa w Private Dock Luxury Heated POOL & Hot tub
9.6 out of 10, Exceptional, (54)
"House was really cute. Everything was as listed. Property owner was very responsive with any questions or concerns. Nice quiet canal location. "
Tampa Villa w Private Dock Luxury Heated POOL & Hot tub
This centralized location is close to everything Tampa Bay has to offer.
10.0 out of 10, Exceptional, (10)
"In town for the weekend my son's wedding. House was perfect. Mother joined us 2nd day and there we was plenty of room"
This centralized location is close to everything Tampa Bay has to offer.
Close to all with a King-bed! Bikes included
9.6 out of 10, Exceptional, (39)
"Adorable place, great location - would stay again!"
The price is CA $117
CA $281 total
includes taxes & fees
Dec 3 - Dec 4
Close to all with a King-bed! Bikes included
Newly renovated home! 1 mile from Downtown & St. Pete Pier
10.0 out of 10, Exceptional, (4)
"Cute 2 bedroom home. Nice area and easy to get around Host always answered any questions we might have. "
Newly renovated home! 1 mile from Downtown & St. Pete Pier
Upscale 4 BR Ybor Hse with Outdoor Living Space (Has Power)
9.4 out of 10, Exceptional, (3)
"Beautiful interior decorations, plenty of entertaining space. The outside area was a hit. Great communication with the owning agency, given that Hurricane Milton had just hit the area."
The price is CA $203
CA $539 total
includes taxes & fees
Nov 12 - Nov 13
Upscale 4 BR Ybor Hse with Outdoor Living Space (Has Power)
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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Other property types in Oldsmar

Chase Suite Hotel Rocky Point Tampa
3.0 star property
7.6 out of 10, Good, (4579)
"The room seems a little outdated. Needs to be more modern. The shower was lukewarm and would not warm up. Apart from that, the stay was good and I would stay again. The staff were very courteous and friendly."
The price is CA $214
CA $243 total
includes taxes & fees
Nov 18 - Nov 19
Chase Suite Hotel Rocky Point Tampa
Sailport Waterfront Suites
3.5 star property
8.4 out of 10, Very good, (4316)
"Was a great place. Visited after hurricane so I not counting the damage in this review "
The price is CA $199
CA $251 total
includes taxes & fees
Nov 18 - Nov 19
Sailport Waterfront Suites
Mint House St. Petersburg - Downtown
4.5 star property
9.4 out of 10, Exceptional, (512)
"The property was lovey. They did have an issue with the valet system."
The price is CA $237
CA $268 total
includes taxes & fees
Nov 25 - Nov 26
Mint House St. Petersburg - Downtown
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.