Holiday, FL Condos for Rent

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

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Our top choices for Holiday condo rentals

A hotel room with two beds, a television, a desk with a computer, and a window with curtains.

1. Cozy Condo Steps From Valspar! Putting, Wine, TV

Palm Harbor

Jason

$187 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern building with a flat roof and large windows.

2. Beautiful condo on Copperhead. Beaches nearby!

Palm Harbor

Indy J.

$247 nightly

Oct 26 - Oct 27

Total with taxes and fees

A modern kitchen with dark cabinetry, a stainless steel sink, and a bar area with a stool.

3. Private nudist resort! New AC & sectional. rent 3 get 1 free. Spring specials

Paradise Lakes

Anonymous traveler

$166 nightly

Oct 26 - Oct 27

Total with taxes and fees

Rows of beach chairs and umbrellas, suggesting a beach resort setting.

4. Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes

Dunedin

Martha E.

$301 nightly

Oct 25 - Oct 26

Total with taxes and fees

A pool area with lounge chairs and umbrellas, a clear sky, and a view of the sea.

5. Dunedin Condo on the Water

Dunedin

Jan D.

$264 nightly

Oct 25 - Oct 26

Total with taxes and fees

A beach with a pier, palm trees, and a building with a dome roof.

6. BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS

Clearwater

Barbara S.

$242 nightly

Nov 17 - Nov 18

Total with taxes and fees

A pool area with lounge chairs, palm trees, and a building with multiple windows.

7. An oasis of serenity: secluded 1BR w/ King Bed, Free parking, Free Gym, Pool

Clearwater

David D.

$254 nightly

Nov 10 - Nov 11

Total with taxes and fees

A sunset view over a body of water with palm trees and buildings in the foreground.

8. Waterfront Oasis on the Gulf

Hudson

Stan H.

$350 nightly

Oct 31 - Nov 1

Total with taxes and fees

A beach with a pier, palm trees, and a pool area.

9. CHARMING CONDO MINUTES FROM GORGEOUS BEACHES & LOTS OF ATTRACTIONS

Clearwater

thomas r.

$230 nightly

Oct 25 - Oct 26

Total with taxes and fees

A modern kitchen with stainless steel appliances, white cabinetry, a microwave, and a built-in oven.

10. Brithday Suit Suite with WiFi in Paradise Lakes Clothing Optional Complex

Lutz

Connie E.

$192 nightly

Oct 25 - Oct 26

Total with taxes and fees

A beach with thatched umbrellas, palm trees, and lounge chairs.

11. Waterfront 1BR 2 Beds Condo at SailPort on Tampa Bay

Rocky Point

$175 nightly

Oct 26 - Oct 27

Total with taxes and fees

12. Condo On The Beach - Heated Pool - Self Check-in

Belleair Beach

Todd A.

$214 nightly

Nov 3 - Nov 4

Total with taxes and fees

A pool area with lounge chairs and a view of the sunset over the ocean.

13. Studio On The Beach - Heated Pool - Self Check-in

Belleair Beach

Jerry R.

$196 nightly

Nov 2 - Nov 3

Total with taxes and fees

14. Pelican Pointe 221:Walk to Beach~Pool~Free Parking

Clearwater Beach

Gail R.

$178 nightly

Oct 29 - Oct 30

Total with taxes and fees

15. Tampa Bay 1BR - Pool & Private Balcony

Rocky Point

ligia

A modern kitchen with white cabinets, stainless steel appliances, and pendant lighting.

16. The Kraken-6-pass golf cart! Plus Pool

Indian Rocks Beach

"We absolutely loved staying here, truly feels like a home away from home. They have thought of all the things you need to have a stress free enjoyable beach vacation. We have two young kids and the beach cart and toys were perfect for a quick walk to the beach. The pool was great and clean for those lazy days to hang out at home. Our family plans on staying again next year and bringing another family to rent the entire building. Lovely stay!"

Danielle D.

$306 nightly

Oct 25 - Oct 26

Total with taxes and fees

A beach with clear blue water, a sandy shore, and a few people.

17. 2/2 Penthouse, Clearwater Beach, 801 Avalon!

Clearwater

Scott S.

$434 nightly

Oct 28 - Oct 29

Total with taxes and fees

18. Pelican Pointe 116:Walk to Beach~Pool~Free Parking

Clearwater Beach

Robert

$190 nightly

Nov 4 - Nov 5

Total with taxes and fees

19. BEST BEACH LOCATION 1 Bedroom w KING BED,Htd POOL 2 FIREPLACE 2 TVs FREE PARKING

Clearwater

Laura M.

$194 nightly

Nov 16 - Nov 17

Total with taxes and fees

A beach swing with a palm tree, overlooking a calm sea at sunset.

20. Direct water view from Balcony-Pool

Rocky Point

Stefanie M.

$228 nightly

Nov 2 - Nov 3

Total with taxes and fees

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Top Holiday Hotel Reviews

Opal Sands Resort

10/10 Excellent

"Perfect holidays experience!!!"

Hyatt Regency Clearwater Beach Resort and Suites

10/10 Excellent

"Stayed at the Hyatt Regency at Clearwater Beach & everything was excellent! Friendly staff, clean & nice lodging/communal spaces, gorgeous rooftop pool & hot tub, plus direct access to the beach w/ cabana/lounge chair rentals at a discount. The Sandava Spa at the resort was very nice w/ a calming atmosphere & my masseuse Myrtha was excellent & friendly! While checking-in, we also were treated to a free upgrade on our room w/ a balcony view of the beach & full kitchen, which was such a lovely surprise! The location is walking distance to so many restaurants, shops, boating excursions, and attractions. Would definitely book with this resort again!"

CW Resort

10/10 Excellent

"⭐⭐⭐⭐⭐ 5 Stars – Absolutely Loved CW Resort!! I honestly cannot say enough good things about CW Resort in Clearwater Beach!! Booked this place last minute, and I couldn’t have been happier with our decision. What an absolutely beautiful resort! First off, the CLEANLINESS!! I’m still talking about how immaculate CW was! From the moment you walk through the doors, everything is spotless, & the entire resort smells AMAZING!! You can immediately tell how much pride they take in maintaining this property, and that is something you just don’t find everywhere these days! The rooms were incredibly spacious, comfortable, and beautifully kept. The pool area was gorgeous, with such a beautiful view of the bay. It was the perfect place to relax and enjoy ourselves! The location couldn’t be better either — literally a 3-minute walk to the beach and all the restaurants, shops, and excitement of Clearwater Beach! And I can’t forget the staff! Every single person we encountered was so friendly, welcoming, and attentive. You can tell they genuinely care about their guests and the experience they provide. We couldn’t have had a better stay! I’m STILL raving about this resort, especially how incredibly clean and beautiful everything was. CW Resort exceeded our expectations, and we would absolutely stay here again in a heartbeat! To the owners, management, and entire staff, THANK YOU for taking pride in your establishment. It truly shows in every little detail, and it doesn’t go unnoticed!"

Find out more about Holiday

Holiday Condo Rentals information

Number of reviews	553
Accommodation	1251 Condo Rentals
Lowest Price	$183
Highest Price	$477

Frequently asked questions

How much do condos in Holiday cost?

Condos in Holiday range from $183 to $477 per night. These stays provide loads of room for the whole family at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many condos are there in Holiday?

Choose from 1251 condos in Holiday. Whether you're vacationing with the family or planning a weekend escape with your besties, Expedia can help you find the ideal base for your crew.

Why book your condo in Holiday with Expedia?

Vacays shouldn't be hard, so if you're in search of condos at a competitive rate, Expedia has got you covered. Keep the budget in check and check in to something small and affordable, or book a luxury condo and really spoil your crew. Take advantage of our search filters to find a place in Holiday that suits you best.

How can I find cheap condos in Holiday?

Expedia can help you locate cheap condos in Holiday. To reserve your dream stay in a few quick keystrokes, simply use our handy filter tool to refine your search results by budget, star rating and amenities.

What is there to do in Holiday near my condo?

If you'd like to explore the best of Holiday, check out Anclote River Park. It's a favorite among locals and visitors alike.

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Our top choices for Holiday condo rentals

1. Cozy Condo Steps From Valspar! Putting, Wine, TV

2. Beautiful condo on Copperhead. Beaches nearby!

3. Private nudist resort! New AC & sectional. rent 3 get 1 free. Spring specials

4. Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes

5. Dunedin Condo on the Water

6. BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS

7. An oasis of serenity: secluded 1BR w/ King Bed, Free parking, Free Gym, Pool

8. Waterfront Oasis on the Gulf

9. CHARMING CONDO MINUTES FROM GORGEOUS BEACHES & LOTS OF ATTRACTIONS

10. Brithday Suit Suite with WiFi in Paradise Lakes Clothing Optional Complex

11. Waterfront 1BR 2 Beds Condo at SailPort on Tampa Bay

12. Condo On The Beach - Heated Pool - Self Check-in

13. Studio On The Beach - Heated Pool - Self Check-in

14. Pelican Pointe 221:Walk to Beach~Pool~Free Parking

15. Tampa Bay 1BR - Pool & Private Balcony

16. The Kraken-6-pass golf cart! Plus Pool

17. 2/2 Penthouse, Clearwater Beach, 801 Avalon!

18. Pelican Pointe 116:Walk to Beach~Pool~Free Parking

19. BEST BEACH LOCATION 1 Bedroom w KING BED,Htd POOL 2 FIREPLACE 2 TVs FREE PARKING

20. Direct water view from Balcony-Pool

Find vacation rentals that suit your style

Top Holiday Hotel Reviews

Opal Sands Resort

Find out more about Holiday

Holiday Condo Rentals information

Frequently asked questions

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