A beach with people standing and facing the ocean, with their arms raised. There are two suitcases on the sand.

Holiday Vacation Rentals

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Our top choices for Holiday vacation rentals

Lakefront Anglers Oasis in Holiday! 8 Mi to Beach

Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
3.0 star property
Tahitian Development
$578 nightly
The price is $644
Jun 22 - Jun 23
Total with taxes and fees
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach

Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very Good, (5,075 reviews)
$113 nightly
The price is $126
Jul 5 - Jul 6
Total with taxes and fees
Sailport Waterfront Suites

Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (743 reviews)
"Excellent accommodations for the price point"
United States
Yvette
$178 nightly
The price is $199
Jun 22 - Jun 23
Total with taxes and fees
Beso Del Sol Resort

Canopy Cove Stunning 2BR Apt Heart of Downtown

Canopy Cove Stunning 2BR Apt Heart of Downtown
2.0 star property
Safety Harbor
$433 nightly
The price is $489
Jun 29 - Jun 30
Total with taxes and fees
Canopy Cove Stunning 2BR Apt Heart of Downtown

2631 Cedarglen Drive

2631 Cedarglen Drive
3.0 star property
Barrington Hills
$2,637 nightly
The price is $2,979
Jul 19 - Jul 20
Total with taxes and fees
2631 Cedarglen Drive

'driftwood Beach Suite' - Walk to Clearwater Bch

'driftwood Beach Suite' - Walk to Clearwater Bch
3.0 star property
Clearwater Beach
$515 nightly
The price is $579
Jul 10 - Jul 11
Total with taxes and fees
'driftwood Beach Suite' - Walk to Clearwater Bch

The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (560 reviews)
"Love the small feel and right on the beach"
United States
Danielle
$242 nightly
The price is $274
Jun 28 - Jun 29
Total with taxes and fees
The Avalon Club

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, (6 reviews)
"This place was double booked. I never received any type of communication from the property then had to find a place to stay because I wasn’t told it was double booked until I showed up and there was people already in the house. I do NOT recommend this place. "
United States
Savanah
$352 nightly
The price is $379
Jun 22 - Jun 23
Total with taxes and fees
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

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
$1,978 nightly
The price is $1,978
Jun 29 - Jun 30
Total with taxes and fees
Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa

Ocean Front Beach in Clearwater 2BB 2BA

Ocean Front Beach in Clearwater 2BB 2BA
3.0 star property
Clearwater Beach
6.8 out of 10, (9 reviews)
"Great location, easy walk to the beach and local spots and the apartment itself was beautiful and a great view. Will be back!!"
United States
Chris
$325 nightly
The price is $367
Jun 29 - Jun 30
Total with taxes and fees
Ocean Front Beach in Clearwater 2BB 2BA

The Hemingway

The Hemingway
4.0 star property
Rocky Point
8.2 out of 10, Very Good, (28 reviews)
"Loved the decor!"
United States
Lauren
$228 nightly
The price is $259
Jun 30 - Jul 1
Total with taxes and fees
The Hemingway

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
$1,420 nightly
The price is $1,605
Jun 28 - Jun 29
Total with taxes and fees
The Gemma by Brightwild

Spacious 3BR 2BA w Pool Gym Near Airport 4

Spacious 3BR 2BA w Pool Gym Near Airport 4
3.0 star property
Westchase
$392 nightly
The price is $444
Jun 22 - Jun 23
Total with taxes and fees
Spacious 3BR 2BA w Pool Gym Near Airport 4

3442 Azalea Pl

3442 Azalea Pl
2.0 star property
Largo
$2,684 nightly
The price is $3,033
Jun 25 - Jun 26
Total with taxes and fees
3442 Azalea Pl

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

Fish & Kayak: Palm Harbor Studio w/ Pool Access!
3.0 star property
Palm Harbor
$181 nightly
The price is $204
Jun 25 - Jun 26
Total with taxes and fees
Fish & Kayak: Palm Harbor Studio w/ Pool Access!

Modern 2BR 2BA w King Bed Pool Gym 10

Modern 2BR 2BA w King Bed Pool Gym 10
3.0 star property
Town 'n' Country
$287 nightly
The price is $326
Jun 29 - Jun 30
Total with taxes and fees
Modern 2BR 2BA w King Bed Pool Gym 10

1465 Satsuma Street

1465 Satsuma Street
2.5 star property
Clearwater
$2,634 nightly
The price is $2,977
Jul 1 - Jul 2
Total with taxes and fees
1465 Satsuma Street

6 Mi to Honeymoon Island: Studio w/ Pool Access

6 Mi to Honeymoon Island: Studio w/ Pool Access
3.0 star property
Palm Harbor
$174 nightly
The price is $193
Jun 22 - Jun 23
Total with taxes and fees
6 Mi to Honeymoon Island: Studio w/ Pool Access

Modern 2BR Pool Gym Pet-friendly 12

Modern 2BR Pool Gym Pet-friendly 12
3.0 star property
Town 'n' Country
$292 nightly
The price is $331
Jul 15 - Jul 16
Total with taxes and fees
Modern 2BR Pool Gym Pet-friendly 12

3485 Floral Drive SE

3485 Floral Drive SE
3.0 star property
Largo
$2,457 nightly
The price is $2,777
Jun 25 - Jun 26
Total with taxes and fees
3485 Floral Drive SE
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 $126 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 70 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. Clearwater Beach 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.