Holiday Homes in Oldsmar

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Featured Holiday Homes in Oldsmar and around

House with unique style 3/2 Near Raymond Stadium

9.2 out of 10, Wonderful, (25)
"Clean and comfortable. Loved the master bath and the coffee."
The price is €374
includes taxes & fees
29 Nov - 30 Nov
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, (243)
"Beautiful condo on a beautiful beach, doesn't get any better 😀 "
1 Bedroom Penthouse Suite located within the Sandpearl Resort & Spa

* Cozy Beach House * Look No Further *

10.0 out of 10, Exceptional, (138)
"We stayed at this incredible property for a short family getaway. It was comfortable and spacious enough for our family of six. The backyard oasis complete with spa area, sandy beach seating area, and picnic table was a nice touch. Our hosts were extremely responsive and helpful whenever we needed assistance. Great property in a quiet neighborhood with many amenities!"
The price is €450
includes taxes & fees
24 Nov - 25 Nov
* Cozy Beach House * Look No Further *

Private entrance room & bathroom w/ courtyard 10 min to beach & Downtown

10.0 out of 10, Exceptional, (30)
"Cozy and comfortable. Clean and private. Driveway parking and courtyard sitting. Great bed. I would come back"
The price is €131
includes taxes & fees
8 Dec - 9 Dec
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, (98)
"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, (36)
"Very nice clean home. The host responds quickly. Very nice yard for our dog. Will stay again."
The price is €290
includes taxes & fees
1 Dec - 2 Dec
Rockin' home near Hard Rock, Fairgrounds, and MidFlorida Amphitheater.

Tampa's Paradise

9.8 out of 10, Exceptional, (8)
"My friends and I enjoyed our stay here. They came to visit from New York so this was a lovely home away from home. The game room and pool were our favorite things about the home and would definitely stay again for a visit."
The price is €773
includes taxes & fees
25 Nov - 26 Nov
Tampa's Paradise

The Great Escape 3BR 2B Entire house

10.0 out of 10, Exceptional, (75)
"This was exactly what we needed for a great weekend in Tampa. Well kept pack n play. They had lots of cooking supplies and children’s utensils. Very responsive. No hurricane damage. Sweet welcome gift upon arrival. "
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, (43)
"Great location. We were able to get to our locations very easily. Very nice open kitchen to living room and also the patio space was perfect for our group. "
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

8.0 out of 10, Very good, (34)
"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!"
☀Shelley Casa, 3BR/2BA,Stunning- ✔Pool✔WHOLE HOUSE

Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass

9.6 out of 10, Exceptional, (210)
"I would highly recommend staying here! We will be back! The beach was just steps away!"
The price is €478
includes taxes & fees
1 Dec - 2 Dec
Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass

Cozy private 1 bedroom & bath Suite in the "Sunshine City" min's to beaches/city

9.8 out of 10, Exceptional, (86)
"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, (44)
"My husband and I stayed for 6 nights. We had such a relaxing time in what seemed like paradise. The property and pool were fabulous. The decor inside and outside is absolutely gorgeous. Such artistry by the owners. The copper gates and artwork around the pool were really awesome. The bed is extremely comfortable as well. "
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, (55)
"Great place, location and loved the pool and hot tub. Play room fun too! TV provided youtube access for NFL games which was a bonus! Shame the fire pit didn't work but everything else perfect."
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, (11)
"As we were only in town for a long weekend the property served us extremely well. My chef of a daughter was especially happy with the kitchen appliances and service items. "
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, (41)
"Adorable place, great location - would stay again!"
The price is €199
includes taxes & fees
10 Dec - 11 Dec
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, (5)
"We enjoyed our stay, great location. Well appointed with an accurate listing, it was just what we needed for a quick couple nights in St. Pete, with this reasonable price we would definitely stay again. Thank you. "
Newly renovated home! 1 mile from Downtown & St. Pete Pier
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, (4618)
" well designed property, what a central location to many of the areas amenities. the staff was very professional, hospitable and genuinely willing to assist with any needs. I would definitely revisit this location and recommended to anyone planning to visit Tampa area"
The price is €131
includes taxes & fees
24 Nov - 25 Nov
Chase Suite Hotel Rocky Point Tampa

Sailport Waterfront Suites

3.5 star property
8.4 out of 10, Very good, (4321)
"Right next to the water "
The price is €150
includes taxes & fees
1 Dec - 2 Dec
Sailport Waterfront Suites

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3100)
"This is my favorite hotel to stay when we visit family in Tampa. We love the pools, hot tubs, Cafe. and views of beach from Baloney.. "
The price is €228
includes taxes & fees
11 Dec - 12 Dec
Sunset Vistas Two Bedroom Beachfront 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.