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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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Holiday vacation rentals

A modern living room with a white sofa, a yellow armchair, a dining table with chairs, and artwork on the walls.

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

Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
3.0 star property
Tahitian Development
The price is ￥42,937
￥106,812 total
includes taxes & fees
Oct 5 - Oct 6
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
A beach with thatched umbrellas and lounge chairs, a sandy shore, and a sunset in the background.

2. Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (5,244 reviews)
"Great location with fun pool and bar!"
United States
Amy
The price is ￥17,279
￥22,470 total
includes taxes & fees
Oct 12 - Oct 13
Sailport Waterfront Suites
A waterfront hotel with multiple balconies, a dock, and a reflective water surface.

3. Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.6 out of 10, Excellent, (768 reviews)
"Loved the view, pool area very nice"
United States
Tracey
The price is ￥16,987
￥25,109 total
includes taxes & fees
Sep 27 - Sep 28
Beso Del Sol Resort
A hotel with a pool area, palm trees, and a view of the ocean.

4. Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel
2.5 star property
Clearwater Beach
9.0 out of 10, Wonderful, (1,137 reviews)
"loved the stay"
United States
Carina Yamilet
The price is ￥13,970
￥24,649 total
includes taxes & fees
Sep 30 - Oct 1
Pelican Pointe Clearwater Beach Hotel
A balcony with wicker furniture overlooking a beach.

5. The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (606 reviews)
"Perfect location on the beach and close to many shops and restaurants."
United States
Robert
The price is ￥35,366
￥46,243 total
includes taxes & fees
Sep 30 - Oct 1
The Avalon Club
A beach with thatched umbrellas and sun loungers facing the ocean.

6. The Palm Exclusive Tropical Luxury on the Water

The Palm Exclusive Tropical Luxury on the Water
3.0 star property
Rocky Point
7.0 out of 10, Good, (4 reviews)
"It is not on the beach. Pictures misleading….Door was broken, bathtub flooded in minutes and fire alarm would go off when a hot shower was took. Quick to take ur money for early check-in/late check out almost could feel the greed. But nice pool war with amazing bartender and food."
United States
Rehan
The price is ￥13,389
￥32,205 total
includes taxes & fees
Sep 29 - Sep 30
The Palm Exclusive Tropical Luxury on the Water
A sandy beach path with vegetation on either side.

7. 'driftwood Beach Suite' - Walk to Clearwater Bch

'driftwood Beach Suite' - Walk to Clearwater Bch
3.0 star property
Clearwater Beach
The price is ￥40,005
￥82,512 total
includes taxes & fees
Sep 27 - Sep 28
'driftwood Beach Suite' - Walk to Clearwater Bch
A beachside seating area with a fire pit and chairs, overlooking the ocean.

8. The Hemingway

The Hemingway
4.0 star property
Rocky Point
8.6 out of 10, Excellent, (40 reviews)
"The property was beautiful,loved the pool and bar restaurant,everyone was so nice.Perfect location to everything"
United States
Michelle
The price is ￥11,324
￥38,130 total
includes taxes & fees
Oct 27 - Oct 28
The Hemingway
A bedroom with a bed, a ceiling fan, a flat-screen TV, a dresser, a mirror, and a walk-in closet.

9. 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
The price is ￥28,594
￥56,046 total
includes taxes & fees
Oct 24 - Oct 25
Sleeps 6 Hot Tub Fenced Yard Cozy Chic
A modern kitchen with white cabinetry, stainless steel appliances, and a central island.

10. 2631 Cedarglen Drive

2631 Cedarglen Drive
3.0 star property
Barrington Hills
The price is ￥352,171
￥494,137 total
includes taxes & fees
Sep 29 - Sep 30
2631 Cedarglen Drive
A swimming pool with hot tubs, a covered patio area, and a well-lit interior space.

11. Tampa Oasis: Pool & Hot Tub Retreat for Families

Tampa Oasis: Pool & Hot Tub Retreat for Families
3.5 star property
Lake Magdalene
Tampa Oasis: Pool & Hot Tub Retreat for Families
A modern kitchen with a large island, white cabinetry, and a dining area with a table and chairs.

12. The Gemma by Brightwild

The Gemma by Brightwild
5.0 star property
Clearwater Beach
9.8 out of 10, Exceptional, (7 reviews)
"Amazing property"
United States
Rusty
The price is ￥107,747
￥228,489 total
includes taxes & fees
Oct 7 - Oct 8
The Gemma by Brightwild
A stone pool surrounded by tropical plants and palm trees.

13. Vibrant 2BR 2BA w King Bed Pool Gym 11

Vibrant 2BR 2BA w King Bed Pool Gym 11
3.0 star property
Town 'n' Country
10.0 out of 10, Exceptional, (1 review)
"Sehr groß und sauber. Alle Möbel waren sauber und funktionsfähig."
Germany
Kim Viola
The price is ￥25,577
￥57,731 total
includes taxes & fees
Oct 20 - Oct 21
Vibrant 2BR 2BA w King Bed Pool Gym 11
A modern kitchen with a large island, stainless steel appliances, and a chandelier.

14. Furnished Outdoor Area! Family Home in Spring Hill

Furnished Outdoor Area! Family Home in Spring Hill
3.0 star property
Spring Hill
8.0 out of 10, Very good, (1 review)
"The house is fresh inside and accommodated our family of 4 wonderfully. We had extra towels and extra pillows which went a long way. Loved the washer and dryer option and the pool. "
United States
Alicia
Furnished Outdoor Area! Family Home in Spring Hill
A modern living room with a blue sofa, a wooden floor, and a ceiling light fixture.

15. 1465 Satsuma Street

1465 Satsuma Street
2.5 star property
Clearwater
The price is ￥348,910
￥480,777 total
includes taxes & fees
Sep 29 - Sep 30
1465 Satsuma Street
A pool area with palm trees, lounge chairs, and umbrellas.

16. Serenity on the Sea Luxury Condo w Prvt Balcony

Serenity on the Sea Luxury Condo w Prvt Balcony
2.0 star property
Rocky Point
8.0 out of 10, Very good, (5 reviews)
"Close to the airport. The beach was great with lounge chairs, tables and umbrellas, but no access to the water. A pool and pool bar was appreciated. The unit was clean, but needed some improvements. The sofa bed and furniture were cheap and not sturdy. More towels are necessary when 4 people are staying."
United States
amy
The price is ￥16,765
￥38,165 total
includes taxes & fees
Sep 28 - Sep 29
Serenity on the Sea Luxury Condo w Prvt Balcony
A sandy beach path leading to the sea with sparse vegetation.

17. Clearwater Beach Hideaway: Walkable Location!

Clearwater Beach Hideaway: Walkable Location!
3.5 star property
Clearwater Beach
The price is ￥53,975
￥137,798 total
includes taxes & fees
Sep 28 - Sep 29
Clearwater Beach Hideaway: Walkable Location!
A modern kitchen with a granite countertop, stainless steel appliances, and white cabinetry.

18. 3442 Azalea Pl

3442 Azalea Pl
2.0 star property
Largo
The price is ￥359,664
￥490,415 total
includes taxes & fees
Sep 29 - Sep 30
3442 Azalea Pl
A beach with a thatched umbrella, sandy shore, and calm sea.

19. Palm Court a Bayview 2 Bed Suite Heated Pool

Palm Court a Bayview 2 Bed Suite Heated Pool
2.0 star property
Rocky Point
10.0 out of 10, Exceptional, (1 review)
The price is ￥17,621
￥38,072 total
includes taxes & fees
Sep 29 - Sep 30
Palm Court a Bayview 2 Bed Suite Heated Pool
A single-story house with a garage, a fenced yard, and a large tree.

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

Fish & Kayak: Palm Harbor Studio w/ Pool Access!
3.0 star property
Palm Harbor
The price is ￥18,874
￥32,199 total
includes taxes & fees
Oct 27 - Oct 28
Fish & Kayak: Palm Harbor Studio w/ Pool Access!
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

The Westin Tampa Bay

The Westin Tampa Bay

10/10 Excellent
"Blog"
Alejandro 1-night trip
Posted 1 hour ago
The Westin Tampa Bay

Find out more about Holiday

Search for holiday rentals in Holiday on Expedia! You can easily find your home rentals, villas, holiday apartments in Holiday using one of the methods below:

  • View our selection of featured holiday rentals in Holiday
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Look no further and take a look at our great range of rental properties in Holiday!

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 69 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.