Holiday Vacation Rentals

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Our top choices for Holiday vacation rentals

3 Mi to Usf: Dog-friendly Home w/ Large Yard

3 Mi to Usf: Dog-friendly Home w/ Large Yard
3.0 star property
Lutz
$719 nightly
The price is $812
Mar 17 - Mar 18
Total with taxes and fees
3 Mi to Usf: Dog-friendly Home w/ Large Yard

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
$479 nightly
The price is $542
Mar 4 - Mar 5
Total with taxes and fees
Waterfront Resort Condo Gulf Sun Set

Serenity on the Sea Luxury Condo w Prvt Balcony

Serenity on the Sea Luxury Condo w Prvt Balcony
2.0 star property
Rocky Point
9.0 out of 10, Wonderful, (2 reviews)
$301 nightly
The price is $342
Mar 1 - Mar 2
Total with taxes and fees
Serenity on the Sea Luxury Condo w Prvt Balcony

Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very Good, (4,930 reviews)
"Room amenities and the view were great."
United States
Andrew
$167 nightly
The price is $188
Mar 29 - Mar 30
Total with taxes and fees
Sailport Waterfront Suites

The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (511 reviews)
"Location , staff and suite all are very good! "
United States
Ali
$294 nightly
The price is $333
Mar 3 - Mar 4
Total with taxes and fees
The Avalon Club

The Gemma by Brightwild

The Gemma by Brightwild
5.0 star property
Clearwater Beach
10.0 out of 10, Exceptional, (2 reviews)
"Amazing property"
United States
Rusty
$1,281 nightly
The price is $1,448
Mar 2 - Mar 3
Total with taxes and fees
The Gemma by Brightwild

Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.8 out of 10, Excellent, (693 reviews)
"It was all great. Clean, staff were very helpful, and very quiet. "
United States
Ethel
$235 nightly
The price is $264
Mar 29 - Mar 30
Total with taxes and fees
Beso Del Sol Resort

The Hemingway

The Hemingway
4.0 star property
Rocky Point
7.8 out of 10, Good, (20 reviews)
"The stay was great! The only issue we had was that their was construction going on throughout our stay which made it less calm and quiet then im sure is typical. "
Canada
Lyndsey
$322 nightly
The price is $365
Mar 1 - Mar 2
Total with taxes and fees
The Hemingway

Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa

Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa
3.0 star property
Allen's Ridge
$1,874 nightly
The price is $1,874
Mar 4 - Mar 5
Total with taxes and fees
Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa

Historic Haven by Downtown Safety Harbor

Historic Haven by Downtown Safety Harbor
2.0 star property
Safety Harbor
$794 nightly
The price is $902
Mar 15 - Mar 16
Total with taxes and fees
Historic Haven by Downtown Safety Harbor

Fish & Kayak: Palm Harbor Studio w/ Pool Access!

Fish & Kayak: Palm Harbor Studio w/ Pool Access!
3.0 star property
Palm Harbor
$152 nightly
The price is $169
Mar 4 - Mar 5
Total with taxes and fees
Fish & Kayak: Palm Harbor Studio w/ Pool Access!

2631 Cedarglen Drive

2631 Cedarglen Drive
3.0 star property
Barrington Hills
$2,821 nightly
The price is $3,188
Mar 6 - Mar 7
Total with taxes and fees
2631 Cedarglen Drive

The Hemingway 2bd Tropical Elegance on the Water

The Hemingway 2bd Tropical Elegance on the Water
2.0 star property
Rocky Point
$306 nightly
The price is $347
Mar 2 - Mar 3
Total with taxes and fees
The Hemingway 2bd Tropical Elegance on the Water

Ocean Front Beach in Clearwater 2BB 2BA

Ocean Front Beach in Clearwater 2BB 2BA
3.0 star property
Clearwater Beach
6.4 out of 10, (8 reviews)
"Parking was easy and pool was clean. View of the water and the boat docks were beautiful. The public beach and area restaurants were walkable. The condo was very clean and spacious. There were beach toys for the children. The washer and dryer were there for use and came in handy. Bring your supplies and you will feel right at home! Thank you for sharing your happy place!!!"
United States
Deborah
$723 nightly
The price is $817
Mar 8 - Mar 9
Total with taxes and fees
Ocean Front Beach in Clearwater 2BB 2BA

Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Sleeps 6 Hot Tub Fenced Yard Cozy Chic
3.0 star property
Town 'n' Country
2.0 out of 10, (4 reviews)
"We were supposed to check in by 3 PM, but when we showed up at 5 PM the cleaners of the house were still there and we had to wait and sit and wait in the driveway until 6 PM until they were finished cleaning. The house smelled like smoke and marijuana and wasn’t the cleanest. "
United States
Joseph
$438 nightly
The price is $477
Feb 28 - Mar 1
Total with taxes and fees
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

Pool & Patio Access: Breezy Getaway in Palm Harbor

Pool & Patio Access: Breezy Getaway in Palm Harbor
3.0 star property
Palm Harbor
$319 nightly
The price is $357
Mar 23 - Mar 24
Total with taxes and fees
Pool & Patio Access: Breezy Getaway in Palm Harbor

3485 Floral Drive SE

3485 Floral Drive SE
3.0 star property
Largo
$2,594 nightly
The price is $2,931
Mar 23 - Mar 24
Total with taxes and fees
3485 Floral Drive SE

Canopy Cove Stunning 2BR Apt Heart of Downtown

Canopy Cove Stunning 2BR Apt Heart of Downtown
2.0 star property
Safety Harbor
$486 nightly
The price is $549
Mar 9 - Mar 10
Total with taxes and fees
Canopy Cove Stunning 2BR Apt Heart of Downtown

6 Mi to Honeymoon Island: Studio w/ Pool Access

6 Mi to Honeymoon Island: Studio w/ Pool Access
Palm Harbor
$161 nightly
The price is $179
Mar 8 - Mar 9
Total with taxes and fees
6 Mi to Honeymoon Island: Studio w/ Pool Access

3442 Azalea Pl

3442 Azalea Pl
2.0 star property
Largo
$2,608 nightly
The price is $2,948
Mar 7 - Mar 8
Total with taxes and fees
3442 Azalea Pl
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 Holiday Hotel Reviews

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 $188 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.

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 63 Expedia vacation rentals in Holiday for a memorable vacation.

What can I see and do in Holiday?

Anclote River Park and Key Vista Nature Park are a couple of lovely local spots to get outside and enjoy nature. Tarpon Springs Sponge Docks and Fred Howard Park 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.