A beach at sunset with birds flying and a person walking.

Oldsmar Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Oldsmar vacation rentals

A beach with thatched umbrellas and lounge chairs, a sandy shore, and a sunset in the background.

1. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,281 reviews)
"Me and my family loved this place ❤️"
United States
Alcendrea
The price is ₩170,919
₩218,161 total
includes taxes & fees
Nov 2 - Nov 3
Sailport Waterfront Suites
A stone pool surrounded by tropical plants and palm trees.

2. Vibrant 2BR 2BA w King Bed Pool Gym 11

Vibrant 2BR 2BA w King Bed Pool Gym 11
3.0 star property
Town 'n' Country
10.0 out of 10, Exceptional, (1 review)
"Sehr groß und sauber. Alle Möbel waren sauber und funktionsfähig."
Germany
Kim Viola
The price is ₩222,134
₩455,785 total
includes taxes & fees
Nov 9 - Nov 10
Vibrant 2BR 2BA w King Bed Pool Gym 11
A waterfront hotel with multiple balconies, a dock, and a reflective water surface.

3. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (778 reviews)
"Loved the view, pool area very nice"
United States
Tracey
The price is ₩144,828
₩214,078 total
includes taxes & fees
Oct 18 - Oct 19
Beso Del Sol Resort
A balcony with wicker furniture overlooking a beach.

4. The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (614 reviews)
"Perfect location on the beach and close to many shops and restaurants."
United States
Robert
The price is ₩314,464
₩408,382 total
includes taxes & fees
Oct 21 - Oct 22
The Avalon Club
A beachside seating area with a fire pit and chairs, overlooking the ocean.

5. The Hemingway

The Hemingway
4.0 star property
Rocky Point
8.4 out of 10, Very good, (42 reviews)
"The property was beautiful,loved the pool and bar restaurant,everyone was so nice.Perfect location to everything"
United States
Michelle
The price is ₩137,587
₩374,009 total
includes taxes & fees
Oct 19 - Oct 20
The Hemingway
An outdoor patio with a dining table, chairs, and a sofa.

6. Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
4.0 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (1,080 reviews)
"Nice stay, clean great location"
Australia
Leah
The price is ₩141,610
₩160,019 total
includes taxes & fees
Nov 8 - Nov 9
Mint House St. Petersburg Downtown by Kasa
A hotel with a pool area, palm trees, and a view of the ocean.

7. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,154 reviews)
"Friendly staff great location rooms were clean and overall very positive"
United States
Bobbi
The price is ₩152,847
₩249,545 total
includes taxes & fees
Oct 18 - Oct 19
Pelican Pointe Clearwater Beach Hotel
An aerial view of a coastal resort area with multiple buildings, a beach, and a marina.

8. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,765 reviews)
"Location was great close to everything. Cafe food was great for breakfast and lunch, Unit could use a little updating, linens definitely need to be replaced."
United States
Michele
The price is ₩228,037
₩295,565 total
includes taxes & fees
Oct 26 - Oct 27
Sunset Vistas Two Bedroom Beachfront Suites
A beach with a large number of people, a seagull flying, and several high-rise buildings in the background.

9. Waterfront Resort Condo Gulf Sun Set

Waterfront Resort Condo Gulf Sun Set
3.0 star property
Dunedin
10.0 out of 10, Exceptional, (3 reviews)
"The place was nice quiet and clean. Nice little tiki bar on site also. Good communication before arrival also. "
United States
joe
The price is ₩341,781
₩632,031 total
includes taxes & fees
Oct 18 - Oct 19
Waterfront Resort Condo Gulf Sun Set
A modern kitchen with a large island, white cabinetry, and a dining area with a table and chairs.

10. The Gemma by Brightwild

The Gemma by Brightwild
5.0 star property
Clearwater Beach
9.8 out of 10, Exceptional, (7 reviews)
"The house was beautiful and the location was perfect for our family."
United States
William
The price is ₩948,087
₩1,972,960 total
includes taxes & fees
Oct 25 - Oct 26
The Gemma by Brightwild
A wooden dock with a fire feature and a 'Please be safe' sign, overlooking a lake with a building in the background.

11. The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (1,020 reviews)
"Great location"
United States
Karen
The price is ₩165,601
₩225,012 total
includes taxes & fees
Nov 1 - Nov 2
The Fold Hotels Indian Shores
A modern living room with a grey sofa, a round wooden coffee table, and a large mirror.

12. Modern 2BR Pool Gym Pet-friendly 12

Modern 2BR Pool Gym Pet-friendly 12
3.0 star property
Town 'n' Country
The price is ₩217,136
₩450,113 total
includes taxes & fees
Oct 20 - Oct 21
Modern 2BR Pool Gym Pet-friendly 12
A bright room with a round table, two chairs, and large windows.

13. The Adaline

The Adaline
5.0 star property
Hyde Park
9.6 out of 10, Exceptional, (76 reviews)
"The best part about this apartment is its location: right by Bayshore, 10 min walking distance from Hyde Park, and in short driving distance from everything S Tampa. The apartment is cute, spacious, quiet, and well equipped. The host provided comprehensive info ahead of check-in so getting in the apartment was smooth."
United States
Mihaela
The price is ₩172,989
₩462,700 total
includes taxes & fees
Oct 18 - Oct 19
The Adaline
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

14. 2631 Cedarglen Drive

2631 Cedarglen Drive
3.0 star property
Barrington Hills
The price is ₩3,164,760
₩4,388,663 total
includes taxes & fees
Oct 19 - Oct 20
2631 Cedarglen Drive
A dining area with a round table, white chairs, a chandelier, and a window with blinds.

15. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,052 reviews)
"Loved our stay!"
United Kingdom
HANNAH
The price is ₩159,579
₩200,023 total
includes taxes & fees
Oct 18 - Oct 19
Barefoot Beach Resort
A dining table with a birthday cake, champagne, and a scenic waterfront view.

16. FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,263 reviews)
"Love this place."
United States
Marilyn
The price is ₩240,173
₩316,856 total
includes taxes & fees
Oct 18 - Oct 19
FUSION Resort Waterfront Suites
A beach with numerous white tents and a sandy beach.

17. Surf Beach Treasure Island Resort

Surf Beach Treasure Island Resort
3.0 star property
Treasure Island
9.2 out of 10, Wonderful, (904 reviews)
"Clean room, close to beach"
United States
Krishna
The price is ₩246,315
₩531,953 total
includes taxes & fees
Oct 18 - Oct 19
Surf Beach Treasure Island Resort
A two-story hotel with a balcony on the upper floor, a stop sign, and a parking area.

18. John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (479 reviews)
"I love this place and will be spending more time there."
United States
John
The price is ₩114,082
₩150,430 total
includes taxes & fees
Oct 25 - Oct 26
John's Pass Hotel
A multi-story hotel with a curved entrance and balconies on each floor.

19. Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2,408 reviews)
"Loved the balcony and hot tub"
United States
AMY
The price is ₩159,847
₩203,357 total
includes taxes & fees
Oct 25 - Oct 26
Crystal Palms Beach Resort
A hotel with a modern design, featuring a prominent 'South Beach' sign and a 'Beach' sign.

20. South Beach Oceanfront Resort

South Beach Oceanfront Resort
3.0 star property
Sunshine Beach
9.2 out of 10, Wonderful, (1,180 reviews)
"Second year staying there this time we stayed 10 days, clean property ,beautiful view, staff was friendly."
United States
Ronald
The price is ₩212,414
₩429,202 total
includes taxes & fees
Oct 18 - Oct 19
South Beach Oceanfront Resort
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

Gulfview Hotel on the Beach

Gulfview Hotel on the Beach

10/10 Excellent
"The staff is amazing and so friendly. Great location and just love the private beach. The music at the neighboring hotel is a plus"
Roxanne 1-night trip
Posted less than an hour ago
Gulfview Hotel on the Beach

Find out more about Oldsmar

Search for Vacation rentals in Oldsmar on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Oldsmar using one of the methods below:

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Look no further and take a look at our great range of rental properties in Oldsmar!

Frequently asked questions

Can I find vacation rentals in Oldsmar?

Yes, we have vacation rentals where you'll be just 14.9 mi (23.9 km) from Busch Gardens Tampa Bay, giving you a secluded option to escape the hustle and bustle. Visitors like the top-notch restaurants and beaches in Oldsmar. Make sure you have time to check out the theme park and cafes during your trip.

What are some of the best vacation home rentals in Oldsmar?

The Gemma by Brightwild: Visitors like this Oldsmar vacation home rental. It is located on the beach and has an outdoor pool, a private balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family. It offers a terrace, a private yard, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals will I find in Oldsmar?

Expedia has 9 vacation rentals for your stay in Oldsmar.

What can I see and do in Oldsmar?

Explore the area and family-friendly sights such as Busch Gardens Tampa Bay, or get out into nature at a spot like Tampa Bay. In the larger area, you’ll find popular places like Raymond James Stadium and Port Tampa Bay.

What are vacation rentals like in Oldsmar?

Vacation rentals are privately owned properties you can book for a few days or a quick weekend in Oldsmar. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, a vacation rental can offer a sense of security away from public hotel elevators and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.