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Holiday Vacation Rentals

Vacation Rentals in Holiday

waterfront home, every room and space has a water view
9.6 out of 10, Exceptional, 4 reviews
"The house was very clean, located at the end of a cul-de-sac and had beautiful sunset views right from the backyard. The house was well maintained with a comfortable open floor plan. We had a great time."
The price is $110
$386 total
includes taxes & fees
Jun 17 - Jun 18
waterfront home, every room and space has a water view
Sailport Waterfront Suites
3.5 star property
8.4 out of 10, Very Good, 4,144 reviews
"An older condo however it was very clean and peaceful. The views were breathtaking. Excellent location and we had a 2 bedroom condo with views of bay in every room. Customer service was remarkable. The manager was a God send understanding my mistake when booking. He assisted me with making my 70th Birthday very memorable. He was so nice and helpful. "
The price is $161
$201 total
includes taxes & fees
Jun 6 - Jun 7
Sailport Waterfront Suites
Chase Suite Hotel Rocky Point Tampa
3.0 star property
7.6 out of 10, Good, 4,309 reviews
"We’ve stayed here a number of times now on weekend getaways, affordable full-kitchen option in the Tampa area, easy drive to activities in either Tampa or the beaches. WiFi in the rooms is sometimes spotty, otherwise rooms are fine. We enjoy the walk next door to a Bahama Breeze for dinner and hanging out, then easily back to the room for an early start next day. "
The price is $109
$124 total
includes taxes & fees
Jul 5 - Jul 6
Chase Suite Hotel Rocky Point Tampa
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Top Floor , Walk to Beach, Pool, Free Parking, #427, Sleeps 6
8.8 out of 10, Excellent, 25 reviews
"Very quiet. Very comfortable and the staff were very informative and polite. I would highly recommend. .R.Talbert"
Top Floor , Walk to Beach, Pool, Free Parking, #427, Sleeps 6
The Avalon Club
4.0 star property
9.6 out of 10, Exceptional, 305 reviews
"The property was really nice. It was across the street a park that the up-keeping was not that great."
The price is $181
$240 total
includes taxes & fees
Jun 11 - Jun 12
The Avalon Club
Right on the BEACH! Exclusive Lighthouse Towers, Sand Key, Clearwater Beach
10.0 out of 10, Exceptional, 89 reviews
"Vince is a very attentive owner/caring. As the listing says, there is a major project going on with the building. One must be prepared for some days it is very loud and distracting. Not all days, but some days were very loud . It’s not anything to blame the owner for and we knew the patio wasn’t available. Having said that it’s a very nice place , beautiful pool and spa. Beaches in the area are stellar. Nice trolley to Clearwater Beach , about a 5 minute ride . Nice Shopping area a 5 min walk...
Right on the BEACH! Exclusive Lighthouse Towers, Sand Key, Clearwater Beach
Beso Del Sol Resort
2.5 star property
8.6 out of 10, Excellent, 433 reviews
"Extremely clean, very professional and nice staff, well organized property, tiki bar w music simple bar bites great drinks- terrific waterviews and priceless sunsets. Bonus free bikes to explore near by fun in downtown. Thumbs up on that Beso del Sol. Otherwise thumb down - very small rooms - ours was nicely tropical decorated "Studio w kitchenette, balcony waterview (over $200 a night bit overpriced in my opinion)...queen size bed and useless small love seat , plus table w 2 chairs ..oh yes it...
The price is $125
$156 total
includes taxes & fees
Jun 6 - Jun 7
Beso Del Sol Resort
Studio in Clearwater Perfect for 2
2.0 star property
The price is $86
$298 total
includes taxes & fees
Jun 6 - Jun 7
Studio in Clearwater Perfect for 2
Dolphin Watch Beach & Dock
9.2 out of 10, Wonderful, 23 reviews
"Overall we enjoyed our stay at this property. It is walking distance to public beach access, food and entertainment. We loved the filtered water in the sink; the included parking; the beach toys for our use; the washer/dryer; and of course, the amazing view of Clearwater Bay from the front porch. There were plenty of towels and extra sheets provided as well. We only stayed 3 nights, but by the end of it, we were feeling pretty cramped and were not fans of the layout of the space. There were...
The price is $173
$383 total
includes taxes & fees
Jun 11 - Jun 12
Dolphin Watch Beach & Dock
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
9.0 out of 10, Wonderful, 40 reviews
"Super cute almost like a doll house. Awesome location. Clean,no bugs. Not recommended for tall people at all. We not super tall but I’m 5 8 and my husband and boys are 5 9 and 6 foot. We did keep hitting our heads on the ceiling because of the slant. I didn’t give it 5 stars because one it says sleeps 6 I don’t think if we had 6 people we would all fit and we almost did.And it’s pet friendly which was why we chose it there is nowhere to walk the dogs. No grass you literally have to go across the...
The price is $189
$432 total
includes taxes & fees
Jun 8 - Jun 9
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
75 Steps to the beach, 1-2 minute walk
10.0 out of 10, Exceptional, 30 reviews
"Spent 2 days here and thoroughly enjoyed it. So close to a non busy section of the beach where we enjoyed a beautiful sunset. Thankful to Joe for supplying beach chairs and all we could need to make it an enjoyable stay. The cottage was cozy and Joe didn’t scrimp on any part. We will return."
The price is $175
$323 total
includes taxes & fees
Jun 16 - Jun 17
75 Steps to the beach, 1-2 minute walk
Clearwater Ocean Front!
8.0 out of 10, Very Good, 10 reviews
"This place was clean and in such a great location! The view from the back was stunning! Walking distance to many restaurants. We would definitely book this place again"
The price is $236
$619 total
includes taxes & fees
Jun 6 - Jun 7
Clearwater Ocean Front!
New 2br Condo - Minutes from Clearwater Beach
4.0 out of 10, 3 reviews
"Booked and showed up at property still waiting to hear from host about check in information. Host never responded to us or VRBO. Almost 24 hours from home with entire family and no place to stay during Spring Break. VRBO put us up in a hotel miles from destination for two nights. Do not recommend this host or property."
The price is $135
$280 total
includes taxes & fees
Jun 10 - Jun 11
New 2br Condo - Minutes from Clearwater Beach
Bayside Condos Studio 23 Pool, Bay Views. Walk to Beach
9.8 out of 10, Exceptional, 8 reviews
"Simple clean space with enough amenities for an extended stay."
Bayside Condos Studio 23 Pool, Bay Views. Walk to Beach
Great Studio - Only 75 Steps to Clearwater Beach
10.0 out of 10, Exceptional, 111 reviews
"When it says 75 steps to the beach, THEY ARE ABSOLUTELY CORRECT!! The loft was stocked with everything you need from our beach getaway!! Joe is a wonderful host! He made sure we had everything we needed!! We plan to return very soon!"
The price is $185
$349 total
includes taxes & fees
Jun 30 - Jul 1
Great Studio - Only 75 Steps to Clearwater Beach
Historic Beach Cottage steps from beach. Pet friendly!
9.2 out of 10, Wonderful, 110 reviews
"Pros: Location, cute beach aesthetic, and the amenities. The water pressure is enviable! The main bedroom bed is firm but comfortable and the sheets were soft. Three teens slept comfortably enough on the fold-outs in the living room. Plenty of linens and pillows for all. Correctable Cons: The main bedroom's wall unit AC contains mold/mildew. There was significant termite residue on kitchen floor on arrival (I thought it was spilled coffee grounds at first.) There is no dishwasher in this unit,...
The price is $279
$546 total
includes taxes & fees
Jun 8 - Jun 9
Historic Beach Cottage steps from beach. Pet friendly!
Chic Modern Condo Hotel Suite on the Beach
10.0 out of 10, Exceptional, 83 reviews
"Nice place, clean. Plenty of room on the beach."
The price is $174
$422 total
includes taxes & fees
Jun 10 - Jun 11
Chic Modern Condo Hotel Suite on the Beach
☆Beach & Pool Resort☆ 1 Min Walk To Beach
9.2 out of 10, Wonderful, 11 reviews
"The room was great, clean and ideal. However, the property staff was unprofessional, nasty and racial. This will be the reason I will not stay in this property again. Thank you,"
The price is $80
$253 total
includes taxes & fees
Jun 13 - Jun 14
☆Beach & Pool Resort☆ 1 Min Walk To Beach
4 BR Oasis, water views every room steps to beach!
9.8 out of 10, Exceptional, 59 reviews
"Perfect location, beautiful condo!"
4 BR Oasis, water views every room steps to beach!
Merry's Beach Bay Condo / POOL SIDE / DOCK SIDE / Awesome Location
9.8 out of 10, Exceptional, 153 reviews
"Perfect spot; beautiful, quiet places to relax after enjoying the many beaches around the area."
Merry's Beach Bay Condo / POOL SIDE / DOCK SIDE / Awesome Location
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See all available properties in Holiday
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.

Holiday Vacation Rental Travel Info

Other types of properties in Holiday you may be interested in

Holiday Hotel
2.5 star property
6.0 out of 10, 344 reviews
"We were there for a weekend get away. Staff was nice. Rooms need a title work done but it was ok for the price."
The price is $74
$83 total
includes taxes & fees
Jun 6 - Jun 7
Holiday Hotel
Wyndham Grand Clearwater Beach
4.0 star property
9.2 out of 10, Wonderful, 1,890 reviews
"This was a great property. We celebrated our 43 wedding anniversary. It exceded our expectations, will definitely return."
The price is $224
$288 total
includes taxes & fees
Jun 30 - Jul 1
Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa
4.0 star property
7.6 out of 10, Good, 1,643 reviews
"This property was great, location, cleanliness, and great dining options. I had a great experience!! "
The price is $234
$304 total
includes taxes & fees
Jun 9 - Jun 10
Hilton Clearwater Beach Resort & Spa
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.

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 $80 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?

Waterfront home, every room and space has a water view: Visitors give good reviews to this Holiday vacation home rental, which is equipped with a fireplace, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Holiday?

Choose from 95 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. Anclote Gulf 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.

Recent reviews of Holiday properties
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