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Holiday Holiday Rentals

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Our top choices for Holiday holiday rentals

Sailport Waterfront Suites

Sailport Waterfront Suites
3.5 star property
Rocky Point
8.4 out of 10, Very good, (4863)
"Great fishing spot,with a great view."
United States
Shanetta
The price is S$192
includes taxes & fees
29 Dec - 30 Dec
Sailport Waterfront Suites

The Avalon Club

The Avalon Club
4.0 star property
Clearwater Beach
9.4 out of 10, Exceptional, (492)
"We loved our stay here. Exceeded expectations"
United States
Anne
The price is S$342
includes taxes & fees
6 Jan - 7 Jan, 2026
The Avalon Club

Beso Del Sol Resort

Beso Del Sol Resort
2.5 star property
Dunedin
8.8 out of 10, Excellent, (679)
"Hot tub was really nice, warm and clean"
United States
James
Beso Del Sol Resort

445 Clearwater Hamden

445 Clearwater Hamden
2.0 star property
Clearwater Beach
10.0 out of 10, Exceptional, (1)
"I loved the property. "
United States
WILLAINA
The price is S$404
includes taxes & fees
6 Jan - 7 Jan, 2026
445 Clearwater Hamden

The Hemingway

The Hemingway
4.0 star property
Rocky Point
7.8 out of 10, Good, (19)
"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
The price is S$378
includes taxes & fees
2 Jan - 3 Jan, 2026
The Hemingway

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
The price is S$1,043
includes taxes & fees
30 Dec - 31 Dec
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)
"Great place"
United States
Daniel
The price is S$672
includes taxes & fees
29 Dec - 30 Dec
Waterfront Resort Condo Gulf Sun Set

The Gemma by Brightwild

The Gemma by Brightwild
5.0 star property
Clearwater Beach
10.0 out of 10, Exceptional, (2)
"Amazing property"
United States
Rusty
The price is S$1,911
includes taxes & fees
13 Jan - 14 Jan, 2026
The Gemma by Brightwild

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
The price is S$2,017
includes taxes & fees
6 Jan - 7 Jan, 2026
Villa Valentino Luxury 8br Villa With Heated Pool 8 Bedroom Villa

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)
"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
Sleeps 6 Hot Tub Fenced Yard Cozy Chic

The Hemingway 2bd Tropical Elegance on the Water

The Hemingway 2bd Tropical Elegance on the Water
2.0 star property
Rocky Point
The Hemingway 2bd Tropical Elegance on the Water

Ocean View, Pool & Boat Dock: Indian Rocks Retreat

Ocean View, Pool & Boat Dock: Indian Rocks Retreat
3.0 star property
Indian Rocks Beach
The price is S$953
includes taxes & fees
22 Jan - 23 Jan, 2026
Ocean View, Pool & Boat Dock: Indian Rocks Retreat

The Tarpon Treasure - Family Home 5 Mins to Beach

The Tarpon Treasure - Family Home 5 Mins to Beach
2.0 star property
Tarpon Springs
9.6 out of 10, Exceptional, (4)
"Chill Place great vibes"
United States
Crissie
The Tarpon Treasure - Family Home 5 Mins to Beach

Pearl Suite a Balcony Bayview Suite Htd Pool

Pearl Suite a Balcony Bayview Suite Htd Pool
2.0 star property
Rocky Point
6.0 out of 10, (1)
Pearl Suite a Balcony Bayview Suite Htd Pool

Palm Court a Bayview 2 Bed Suite Heated Pool

Palm Court a Bayview 2 Bed Suite Heated Pool
2.0 star property
Rocky Point
Palm Court a Bayview 2 Bed Suite Heated Pool

Oceans Pointe Nantucket Inspired Condo on the bay

Oceans Pointe Nantucket Inspired Condo on the bay
2.0 star property
Rocky Point
Oceans Pointe Nantucket Inspired Condo on the bay

The Flamingo Balcony Waterview Heated Pool

The Flamingo Balcony Waterview Heated Pool
2.0 star property
Rocky Point
The price is S$391
includes taxes & fees
4 Jan - 5 Jan, 2026
The Flamingo Balcony Waterview Heated Pool

Canopy Cove Stunning 2BR Apt Heart of Downtown

Canopy Cove Stunning 2BR Apt Heart of Downtown
2.0 star property
Safety Harbor
The price is S$674
includes taxes & fees
14 Jan - 15 Jan, 2026
Canopy Cove Stunning 2BR Apt Heart of Downtown

Sunset on the Bay Designer Condo Private Balcony

Sunset on the Bay Designer Condo Private Balcony
2.0 star property
Rocky Point
4.0 out of 10, (2)
"Very unhappy with this stay"
United States
candice
Sunset on the Bay Designer Condo Private Balcony

Studio w/ King Bed Heated Pool, Steps to Beach!

Studio w/ King Bed Heated Pool, Steps to Beach!
2.0 star property
Clearwater Beach
The price is S$393
includes taxes & fees
4 Jan - 5 Jan, 2026
Studio w/ King Bed Heated Pool, Steps to Beach!
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

Frequently asked questions

Can I find holiday rentals in Holiday?

Yes, there are holiday rentals close to the most popular sights in Holiday, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Holiday has to offer?

The Gemma by Brightwild: This holiday home rental outside of Holiday is located on the beach, and has an outdoor pool, a private balcony and a BBQ 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 that you can cook with friends or family. It offers a terrace, a private garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Holiday?

Choose from 67 Expedia holiday rentals in Holiday for a memorable holiday.

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 Lake Tarpon are a couple of places you'll find in the wider area.

What are holiday rentals like in Holiday?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Holiday. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a small group gathering.