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Our top choices for Oldsmar holiday rentals

1. Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed

Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed
Oldsmar
9.8 out of 10, Exceptional, (64 reviews)
"Roomy two BR two full bath house, beautifully maintained with nice lanai and backyard grill in quiet neighborhood. Perfect location for visiting Tampa Bay Downs horse track, Tarpon Springs & Dunedin. Would happily stay here again."
United States
Stephen W.
Oldsmar Oakleaf Villa! On Wildlife Area, Natural Privacy! Patio Garage. King Bed

2. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,319 reviews)
"Our favorite part was the on site bar and restaurant"
United States
Paula A
The price is £115
includes taxes & fees
22 Nov - 23 Nov
Sailport Waterfront Suites

3. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (790 reviews)
"Friendly staff, great location and wonderful views"
United States
Gina
The price is £120
includes taxes & fees
15 Nov - 16 Nov
Beso Del Sol Resort

4. The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (621 reviews)
"The room was spacious for my family and I. A close walk to the beach. Close to shopping and eating, great location."
United States
Courtney
The price is £228
includes taxes & fees
18 Nov - 19 Nov
The Avalon Club

5. Sunset Vistas Two Bedroom Beachfront Suites

Sunset Vistas Two Bedroom Beachfront Suites
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (3,781 reviews)
"I love staying here. This is my 3rd time staying here and I keep coming back because I love the property! The location is ideal, and the staff are amazing."
United States
Shelby
The price is £143
includes taxes & fees
18 Nov - 19 Nov
Sunset Vistas Two Bedroom Beachfront Suites

6. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,184 reviews)
"Hotel was great!"
United States
Daniel
The price is £116
includes taxes & fees
2 Dec - 3 Dec
Pelican Pointe Clearwater Beach Hotel

7. Mint House St. Petersburg Downtown by Kasa

Mint House St. Petersburg Downtown by Kasa
3.5 star property
Downtown St. Petersburg
9.4 out of 10, Exceptional, (1,121 reviews)
"Great place"
United States
Anonymous traveller
The price is £81
includes taxes & fees
25 Nov - 26 Nov
Mint House St. Petersburg Downtown by Kasa

8. Innisbrook 2BR Getaway With Balcony & Pool

Innisbrook 2BR Getaway With Balcony & Pool
Palm Harbor
9.6 out of 10, Exceptional, (30 reviews)
"Place was great and sits on hole 2 of Copperhead. The only catch is the property has no elevator, and the room is on the 3rd floor."
United States
Indy J.
The price is £221
includes taxes & fees
13 Nov - 14 Nov
Innisbrook 2BR Getaway With Balcony & Pool

9. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (36 reviews)
"Had an amazing stay at this beautiful cottage! The place was very clean, spacious, and comfortable, making it the perfect spot to relax and enjoy our time away. I felt safe throughout the stay, and the location was excellent, with cafés and restaurants within walking distance. The host was wonderful (very easy to communicate back and forth with, even left an itinerary with recommendations, LOVEDDD THATTT) and truly, appreciated the opportunity to stay here. Would absolutely recommend this...
United States
Nayeli
The price is £145
includes taxes & fees
15 Nov - 16 Nov
Key West Style Cottage - with pool/hot-tub

10. Cozy Boho Guest House w/Patio - 6 min from the beach!

Cozy Boho Guest House w/Patio - 6 min from the beach!
Town 'n' Country
9.0 out of 10, Wonderful, (40 reviews)
"Very clean, quiet. Safe surroundings if you are traveling by yourself."
United States
Deborah
The price is £78
includes taxes & fees
25 Nov - 26 Nov
Cozy Boho Guest House w/Patio - 6 min from the beach!

11. Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!

Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!
Rocky Point
9.6 out of 10, Exceptional, (114 reviews)
"This place was so cute and large! Great pool area and views! Very clean and would highly recommend!!"
United States
Julie T.
The price is £280
includes taxes & fees
16 Nov - 17 Nov
Amazing Waterfront Views Resort, Enjoy Heated Pool & Sunset!

12. The Fold Hotels Indian Shores

The Fold Hotels Indian Shores
3.0 star property
Indian Shores
9.2 out of 10, Wonderful, (1,027 reviews)
"Great location"
United States
Karen
The price is £130
includes taxes & fees
8 Dec - 9 Dec
The Fold Hotels Indian Shores

13. Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

Welcome to our charming studio, perfectly located near Tampa Bay's attractions.
Pinecrest West Park
9.2 out of 10, Wonderful, (86 reviews)
"Great stay, very clean. The pool was very nice. And the scenery was amazing as well"
United States
Brandy
The price is £67
includes taxes & fees
16 Nov - 17 Nov
Welcome to our charming studio, perfectly located near Tampa Bay's attractions.

14. Green Castle Suite in Tampa

Green Castle Suite in Tampa
Town 'n' Country
9.6 out of 10, Exceptional, (40 reviews)
"Great place to stay!"
United States
Stephanie S.
The price is £92
includes taxes & fees
24 Nov - 25 Nov
Green Castle Suite in Tampa

15. FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites
3.5 star property
Treasure Island
9.2 out of 10, Wonderful, (1,278 reviews)
"Nice place at a reasonable price. Great amenities. Beautiful views"
United States
Andrew
The price is £177
includes taxes & fees
29 Nov - 30 Nov
FUSION Resort Waterfront Suites

16. Barefoot Beach Resort

Barefoot Beach Resort
3.5 star property
Indian Shores
9.0 out of 10, Wonderful, (1,069 reviews)
"Loved our stay!"
United Kingdom
HANNAH
The price is £107
includes taxes & fees
13 Dec - 14 Dec
Barefoot Beach Resort

17. John's Pass Hotel

John's Pass Hotel
2.0 star property
Madeira Beach
8.6 out of 10, Excellent, (506 reviews)
"Love the location having shops around and how easy was to check in"
United States
Luis
The price is £84
includes taxes & fees
18 Nov - 19 Nov
John's Pass Hotel

18. A beautiful and comfortable room, Apartment No. 2

A beautiful and comfortable room, Apartment No. 2
Tampa
10.0 out of 10, Exceptional, (53 reviews)
"Amazing hosts and clean, quiet, super cute place to stay!"
United States
Angela W.
The price is £106
includes taxes & fees
13 Nov - 14 Nov
A beautiful and comfortable room, Apartment No. 2

19. Crystal Palms Beach Resort

Crystal Palms Beach Resort
3.5 star property
Sunshine Beach
8.8 out of 10, Excellent, (2,416 reviews)
"Always a great stay"
United States
Joe
The price is £114
includes taxes & fees
18 Nov - 19 Nov
Crystal Palms Beach Resort

20. Experience the passion of hospitality, cleaning, and good location!

Experience the passion of hospitality, cleaning, and good location!
Westshore
9.2 out of 10, Wonderful, (94 reviews)
"Staff was really nice!"
United States
Anthony
The price is £94
includes taxes & fees
15 Nov - 16 Nov
Experience the passion of hospitality, cleaning, and good location!
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

Find out more about Oldsmar

Everything you need to know about Oldsmar holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Oldsmar holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Oldsmar holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Oldsmar holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Oldsmar. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Oldsmar holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Oldsmar holiday rentals we have selected for you start as low as £81 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Oldsmar rentals

At Expedia, we put the best Oldsmar holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Oldsmar rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Oldsmar holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Oldsmar. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Explore a world of travel with Expedia

Frequently asked questions

Can I find holiday rentals in Oldsmar?

Yes, we have holiday rentals where you'll be only 14.9 mi (23.9 km) from Busch Gardens Tampa Bay, offering you a more remote option if you want a quieter place to stay. Visitors like the top-notch restaurants and beaches in Oldsmar. Make sure you have time to check out the theme park and cafés during your trip.

What are some of the best holiday rentals that Oldsmar has to offer?

The Gemma by Brightwild: This holiday home rental outside of Oldsmar is located on the beach, and has an outdoor pool, a private balcony and a BBQ 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 that you can cook with friends or family. It offers a terrace, a private garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Oldsmar?

Expedia has 9 holiday 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 wider area, you’ll find popular places such as Raymond James Stadium and Port Tampa Bay.

What are holiday rentals like in Oldsmar?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Oldsmar. Holiday rentals feature extras such as hot tubs, fire pits and patios so you'll have all the conveniences of home. If you're concerned about cleanliness, holiday rentals can offer a sense of security away from public hotel lifts and busy concierge desks while still allowing you a great travel experience. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.