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Holiday Vacation Rentals

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Vacation Rentals in Holiday

waterfront home, every room and space has a water view
9.6 out of 10, Exceptional, (4)
"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 CA $150
CA $526 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, (4144)
"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 CA $219
CA $273 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, (4305)
"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 CA $143
CA $162 total
includes taxes & fees
Jun 24 - Jun 25
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)
"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, (304)
"The property was really nice. It was across the street a park that the up-keeping was not that great."
The price is CA $231
CA $309 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)
"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)
"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 CA $238
CA $311 total
includes taxes & fees
Jun 11 - Jun 12
Beso Del Sol Resort
Studio in Clearwater Perfect for 2
2.0 star property
The price is CA $117
CA $405 total
includes taxes & fees
Jun 5 - Jun 6
Studio in Clearwater Perfect for 2
Dolphin Watch Beach & Dock
9.2 out of 10, Wonderful, (23)
"My chief complaint about this property is they charged me a very large security deposit in January for our stay in May. We only got the money back over 2 weeks after we checked out. They had my money for 5+ months. Place was in a great location with a nice pool and walking distance to beach and bars . One bedroom was only accessible through the bathroom or other bedroom. All in all it was a really nice place. Parking was great and it was nicely furnished. Communication with management was great"
The price is CA $236
CA $522 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)
"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 CA $258
CA $589 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)
"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 CA $239
CA $443 total
includes taxes & fees
Jun 5 - Jun 6
75 Steps to the beach, 1-2 minute walk
Clearwater Ocean Front!
8.0 out of 10, Very good, (10)
"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 CA $322
CA $838 total
includes taxes & fees
Jun 12 - Jun 13
Clearwater Ocean Front!
New 2br Condo - Minutes from Clearwater Beach
4.0 out of 10, (3)
"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 CA $184
CA $374 total
includes taxes & fees
Jun 11 - Jun 12
New 2br Condo - Minutes from Clearwater Beach
Bayside Condos Studio 23 Pool, Bay Views. Walk to Beach
9.8 out of 10, Exceptional, (8)
"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)
"cozy studio apartment ,quiet neighborhood a few steps from beach. Nice restaurants on beach nearby. Great time!"
The price is CA $252
CA $475 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)
"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 CA $380
CA $744 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)
"Nice place, clean. Plenty of room on the beach."
The price is CA $238
CA $575 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)
"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 CA $113
CA $355 total
includes taxes & fees
Jun 11 - Jun 12
☆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)
"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)
"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
Don't see what you're looking for?
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)
"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 CA $91
CA $102 total
includes taxes & fees
Jun 18 - Jun 19
Holiday Hotel
Wyndham Grand Clearwater Beach
4.0 star property
9.2 out of 10, Wonderful, (1884)
"We enjoy your stay everything was excellent"
The price is CA $305
CA $393 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, (1639)
"Patio door broken no towels "
The price is CA $333
CA $430 total
includes taxes & fees
Jun 16 - Jun 17
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.

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Holiday. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

Studio in Clearwater Perfect for 2: This vacation home rental outside Holiday comes with WiFi so you can feel at home during your trip. Kitchen amenities like a fridge and an oven can make your vacation run smoothly. Another good choice for your trip to Holiday is waterfront home, every room and space has a water view.

How many vacation rentals are there in Holiday?

Choose from 97 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
Expedia verified reviews