Holiday Vacation Rentals from $136: Search Short-Term Rentals

Q: What are some of the best vacation rentals that Holiday has to offer?

The Gemma by Brightwild : This vacation home rental outside of Holiday 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Holiday vacation rentals

1 bedroom, iron/ironing board, WiFi (free), bed sheets

1. Rest apartament

Holiday

Lee

$120 nightly

Sep 23 - Sep 24

Total with taxes and fees

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

Colonial Hills

Thomas

$134 nightly

Sep 22 - Sep 23

Total with taxes and fees

3. Charming Hot Tub Getaway by Tarpon

Holiday

Daniel R.

$165 nightly

Sep 23 - Sep 24

Total with taxes and fees

4. Convenient close to the sun and fun 3 bed home!

Holiday Lake Estates

Paul V.

$262 nightly

Oct 19 - Oct 20

Total with taxes and fees

5. Luxurious Waterfront Holiday Home with Fully Encompassing Lakeview

Holiday

Jerome D.

$282 nightly

Sep 22 - Sep 23

Total with taxes and fees

Beach nearby, sun loungers, beach towels

6. GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!

Holiday

Glenida R.

$454 nightly

Sep 22 - Sep 23

Total with taxes and fees

7. Seabreeze - Charming 2-bedroom house in amazing Holiday with WiFi, AC.

Holiday

Fallon H.

$258 nightly

Sep 22 - Sep 23

Total with taxes and fees

8. Lakefront Paradise, with Heated Private Pool.

Tahitian Development

Jessica V.

$349 nightly

Oct 18 - Oct 19

Total with taxes and fees

9. Luxury Renovated Home Near Beaches. Pet Friendly.

Holiday

"Comfortable beds and couches. Very lovely modern updates in the aesthetic of the home. There are a couple of fit and finish details that I have contacted the owner about. Particularly for dog owners. One thing I will know is that there’s no direct access to the backyard as of when we rented this. So you have to go out the front and then through a gate to the back. For people with dogs that are challenging for verbal recall this means you have to put on the leash and collar and then go. Don’t...

Rachel R.

$268 nightly

Oct 21 - Oct 22

Total with taxes and fees

10. Beachy Holiday Home- 3/2 up to 5 guests

Holiday

$281 nightly

Sep 22 - Sep 23

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

11. Coastal Family Retreat – Heated Pool, Fire Pit & Fun!

Holiday Lakes West

Kate G.

$360 nightly

Sep 22 - Sep 23

Total with taxes and fees

12. Coastal Family Escape with Private Pool•Near Beaches

Holiday

Terri R.

$434 nightly

Sep 22 - Sep 23

Total with taxes and fees

13. beaches house near by beach

Ridgewood Gardens

$292 nightly

Sep 30 - Oct 1

Total with taxes and fees

14. The Burnside Bungalow where Vacation Awaits!

Holiday

$388 nightly

Sep 22 - Sep 23

Total with taxes and fees

15. Luxe Retreat with Resort-Style Pool Backyard

Holiday

Jason B.

$457 nightly

Sep 22 - Sep 23

Total with taxes and fees

16. Canal-Front Getaway•Poolside Relaxation•Fishing

Holiday Lake Estates

"The pictures don't do this place justice! It's beautiful. There is ample room for family and friends. The pool was perfect and relaxing. We enjoyed using it multiple times daily. The card table was perfect for us playing games each night. The kitchen had really good pans, which is unusual for most rentals. We did have a learning curve with the kitchen faucet but quickly discovered it was tap to start and stop. We might suggest a couple of kitchen towels, but otherwise the kitchen was very...

Chris S.

$451 nightly

Sep 22 - Sep 23

Total with taxes and fees

17. Lakefront Anglers Oasis in Holiday! 8 Mi to Beach

Tahitian Development

$606 nightly

Sep 22 - Sep 23

Total with taxes and fees

18. Lakefront Angler’s Oasis in Holiday! 8 Mi to Beach

Tahitian Development

$588 nightly

Sep 22 - Sep 23

Total with taxes and fees

19. Elegant Coastal Oasis Near Beaches & Private Pool

Holiday Lakes West

Dana F.

$489 nightly

Sep 22 - Sep 23

Total with taxes and fees

20. East Riverside Downtown Bungalow

Downtown

Chris

$226 nightly

Sep 22 - Sep 23

Total with taxes and fees

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Holiday Hotel Reviews

ChartHouse Clearwater Beach Marina Hotel

10/10 Excellent

"Loved this location ! Chart house was very clean. Maid service everyday they did a great job! Pool doesn't get much sun on it throug out the day. Balcony marina veiw was nice. 6th floor we could see the ocean and pier. Jimmys bar is nice, Sarah the bar manager was great! Would defiantly stay again."

Hyatt Regency Clearwater Beach Resort and Suites

10/10 Excellent

"My wife and I had an incredible stay. The hotel was very clean, the staff was amazing, the restaurants and amenities were great. We absolutely loved the stunning pool and it even had a rooftop hot tub. We would highly recommend this hotel if you are in the Clearwater area."

Opal Sol

8/10 Good

"The Opal Sol Resort was beautiful, and our overall stay was very enjoyable. The only reason I did not rate the staff five stars is due to what appeared to be a training gap in explaining and managing credit-card authorization holds. Authorization holds are understandable; however, after extending our stay and providing a second card, approximately $2,000 was tied up across my cards and my father’s card. This left us without access to those funds until checkout, followed by additional waiting time for the card issuers and banks to release the holds. A clearer explanation of the process, along with more careful handling of authorization amounts for extended stays, would greatly improve the guest experience."

HomeTowne Studios by Red Roof Tampa - Airport

10/10 Excellent

"Queen studio room was very clean and immaculate. Nice to have a small kitchenette with paper goods provided at front desk. The only downside was the use of a strong cleaning product. Other than that, would stay at this hotel again. Convenient to Tampa International Airport."

Find out more about Holiday

Everything you need to know about Holiday vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Holiday vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 Holiday vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Holiday vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $136 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Holiday rentals

At Expedia, we put the best Holiday vacation 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 Holiday 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 Holiday vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Holiday. 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 vacation rentals in Holiday?

Yes, we offer vacation rentals close to popular points of interest in Holiday, or you can go with a more secluded option if you're looking for relaxation. Our travelers say Holiday has a good selection of restaurants. Make sure you have time to check out the shopping and beaches during your trip.

What are some of the best vacation rentals that Holiday has to offer?

The Gemma by Brightwild: This vacation home rental outside of Holiday 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 are there in Holiday?

Choose from 68 Expedia vacation rentals in Holiday for a memorable vacation.

What can I see and do in Holiday?

Anclote River Park and Lake Conley are a couple of lovely local spots to get outside and enjoy nature. Key Vista Nature Park and Tarpon Springs Sponge Docks are a couple of places you'll find in the larger area.

What are vacation rentals like in Holiday?

Vacation rentals are privately owned accommodations you can stay in for a few days or a quick weekend in Holiday. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're at home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for family trips.

Holiday Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Holiday vacation rentals

1. Rest apartament

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

3. Charming Hot Tub Getaway by Tarpon

4. Convenient close to the sun and fun 3 bed home!

5. Luxurious Waterfront Holiday Home with Fully Encompassing Lakeview

6. GREAT LOCATION WATERFRONT, HEATED POOL! BEAUTIFUL SUNSETS, ALL PETS STAY FREE!

7. Seabreeze - Charming 2-bedroom house in amazing Holiday with WiFi, AC.

8. Lakefront Paradise, with Heated Private Pool.

9. Luxury Renovated Home Near Beaches. Pet Friendly.

10. Beachy Holiday Home- 3/2 up to 5 guests

11. Coastal Family Retreat – Heated Pool, Fire Pit & Fun!

12. Coastal Family Escape with Private Pool•Near Beaches

13. beaches house near by beach

14. The Burnside Bungalow where Vacation Awaits!

15. Luxe Retreat with Resort-Style Pool Backyard

16. Canal-Front Getaway•Poolside Relaxation•Fishing

17. Lakefront Anglers Oasis in Holiday! 8 Mi to Beach

18. Lakefront Angler’s Oasis in Holiday! 8 Mi to Beach

19. Elegant Coastal Oasis Near Beaches & Private Pool

20. East Riverside Downtown Bungalow

Find vacation rentals that suit your style

Top Holiday Hotel Reviews

ChartHouse Clearwater Beach Marina Hotel

Find out more about Holiday

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app