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

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Holiday condo rentals

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

1. BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS

BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS
Clearwater
9.8 out of 10, Exceptional, (120 reviews)
"Yes great experience !the heated pool i loved! Would do again."
United States
Barbara S.
$212 nightly
The price is $237
Sep 16 - Sep 17
Total with taxes and fees
BEAUTIFUL CONDO MINUTES FROM GORGEOUS BEACHES & FAMILY ATTRACTIONS
Rows of beach chairs and umbrellas, suggesting a beach resort setting.

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

Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes
Dunedin
9.6 out of 10, Exceptional, (96 reviews)
"Perfect for a mini vacation to visit Honeymoon Island and Calideci Island. On site restaurant and bar was great."
United States
ARTHUR G.
$298 nightly
The price is $333
Sep 10 - Sep 11
Total with taxes and fees
Condo in Waterfront Resort - Clearwater Beaches & Honeymoon Island, Free Bikes
A modern kitchen with stainless steel appliances, white cabinetry, a microwave, and a built-in oven.

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

Brithday Suit Suite with WiFi in Paradise Lakes Clothing Optional Complex
Lutz
6.6 out of 10, (7 reviews)
"Both the host and amenities.(See comments in original post)"
United States
Ben B.
$192 nightly
The price is $212
Sep 10 - Sep 11
Total with taxes and fees
Brithday Suit Suite with WiFi in Paradise Lakes Clothing Optional Complex
A beach with thatched umbrellas and colorful Adirondack chairs.

4. 1920s Speakeasy with Waterview & Heated Pool

1920s Speakeasy with Waterview & Heated Pool
Rocky Point
10.0 out of 10, Exceptional, (3 reviews)
"Perfect stay on a great resort. Will definitely stay again."
United States
Deena V.
$275 nightly
The price is $291
Sep 10 - Sep 11
Total with taxes and fees
1920s Speakeasy with Waterview & Heated Pool
A beach with thatched umbrellas and colorful Adirondack chairs.

5. Bay Breeze – Balcony, Heated Pool + Bar & Grill

Bay Breeze – Balcony, Heated Pool + Bar & Grill
Rocky Point
10.0 out of 10, Exceptional, (3 reviews)
"Great location, amenities"
United States
malgorzata c.
$243 nightly
The price is $259
Sep 10 - Sep 11
Total with taxes and fees
Bay Breeze – Balcony, Heated Pool + Bar & Grill
A beach with a pier, palm trees, and a pool area.

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

CHARMING CONDO MINUTES FROM GORGEOUS BEACHES & LOTS OF ATTRACTIONS
Clearwater
9.6 out of 10, Exceptional, (58 reviews)
"Nice stay! We used the pool, cooked and watch tv. "
United States
thomas r.
$238 nightly
The price is $266
Sep 20 - Sep 21
Total with taxes and fees
CHARMING CONDO MINUTES FROM GORGEOUS BEACHES & LOTS OF ATTRACTIONS
A beach swing with a palm tree, overlooking a calm sea at sunset.

7. Direct water view from Balcony-Pool

Direct water view from Balcony-Pool
Rocky Point
9.4 out of 10, Exceptional, (76 reviews)
"Very nice for a quick relaxing getaway!"
United States
Stefanie M.
$224 nightly
The price is $251
Sep 10 - Sep 11
Total with taxes and fees
Direct water view from Balcony-Pool

8. Tampa Bay 1BR - Full Kitchen & Pool Views

Tampa Bay 1BR - Full Kitchen & Pool Views
Rocky Point
$127 nightly
The price is $142
Sep 10 - Sep 11
Total with taxes and fees
Tampa Bay 1BR - Full Kitchen & Pool Views
A pool area with lounge chairs and umbrellas, a clear sky, and a view of the sea.

9. Dunedin Condo on the Water

Dunedin Condo on the Water
Dunedin
9.2 out of 10, Wonderful, (16 reviews)
"Good location. Loved the hot tub looking out over the bay. Great place to watch the sunset."
United States
Jan D.
$285 nightly
The price is $318
Sep 10 - Sep 11
Total with taxes and fees
Dunedin Condo on the Water

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

Studio On The Beach - Heated Pool - Self Check-in
Belleair Beach
9.6 out of 10, Exceptional, (5 reviews)
"Our host was very helpful and quick to respond. The place was pefect for a getaway for 2! Close to everything and a quick walk to the beach. Would stay again!"
United States
STACIA B.
$172 nightly
The price is $192
Sep 14 - Sep 15
Total with taxes and fees
Studio On The Beach - Heated Pool - Self Check-in
A beachside hotel with a sandy beach, palm trees, and umbrellas.

11. Cozy, Remodeled Retreat with Stunning Sunset Views Complete with Heated Pool!

Cozy, Remodeled Retreat with Stunning Sunset Views Complete with Heated Pool!
Rocky Point
9.4 out of 10, Exceptional, (9 reviews)
"Comfortable apartment in a beautiful area. Conveniently located with a handful of nice restaurants nearby. Beautiful sunset and easy covered parking."
United States
Sharon Kehoe M.
$202 nightly
The price is $226
Sep 10 - Sep 11
Total with taxes and fees
Cozy, Remodeled Retreat with Stunning Sunset Views Complete with Heated Pool!

12. Golden Oasis in Clearwater, 3 Heated Pools, 13 Minutes from the Beach! 🏝️

Golden Oasis in Clearwater, 3 Heated Pools, 13 Minutes from the Beach! 🏝️
Clearwater
10.0 out of 10, Exceptional, (9 reviews)
"It was the best place I ever stayed in Florida we go to Florida every year definitely I’m going back to the same place the host Gabrielle was amazing she helped us with everything i recommend this place better from any hotel"
United States
Elias S.
$314 nightly
The price is $350
Sep 11 - Sep 12
Total with taxes and fees
Golden Oasis in Clearwater, 3 Heated Pools, 13 Minutes from the Beach! 🏝️
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

Studio On The Beach - Heated Pool - Self Check-in
Belleair Beach
9.2 out of 10, Wonderful, (15 reviews)
"Wonderful place! Will stay again. "
United States
Jerry R.
$207 nightly
The price is $231
Sep 24 - Sep 25
Total with taxes and fees
Studio On The Beach - Heated Pool - Self Check-in
A living room with a grey sofa, a wooden coffee table, and a dining area with a table and chairs.

14. Beautiful Two Bedroom, Two Bath Condo at Sailport

Beautiful Two Bedroom, Two Bath Condo at Sailport
Rocky Point
10.0 out of 10, Exceptional, (6 reviews)
"We had a great time. The condo is beautiful. The view from the balcony is beautiful. The area was perfect and the tiki bar at the pool had great food and drinks. Already plan on going back. "
United States
Cheryl D.
$406 nightly
The price is $454
Sep 10 - Sep 11
Total with taxes and fees
Beautiful Two Bedroom, Two Bath Condo at Sailport
A beach with thatched umbrellas, blue lounge chairs, and wooden chairs.

15. Waterfront Oasis ⚡ Near Lightning & Bucs Games

Waterfront Oasis ⚡ Near Lightning & Bucs Games
Rocky Point
9.4 out of 10, Exceptional, (59 reviews)
"Great location. "
United States
Gina F.
$220 nightly
The price is $246
Sep 11 - Sep 12
Total with taxes and fees
Waterfront Oasis ⚡ Near Lightning & Bucs Games
A modern kitchen with a large sink, a dining area with a blue sofa and a view of the ocean.

16. Bayfront 2BR/2BA Condo at Sailport – Minutes from Beaches & Downtown Attractions

Bayfront 2BR/2BA Condo at Sailport – Minutes from Beaches & Downtown Attractions
Rocky Point
$412 nightly
The price is $460
Sep 10 - Sep 11
Total with taxes and fees
Bayfront 2BR/2BA Condo at Sailport – Minutes from Beaches & Downtown Attractions
Outdoor seating with blue umbrellas and thatched umbrellas, arranged on a paved patio with views of the sea.

17. Sunset and Serenity @ Sailport Tampa

Sunset and Serenity @ Sailport Tampa
Rocky Point
10.0 out of 10, Exceptional, (3 reviews)
"My stay was quick and easy at Sailport. I didn’t get a chance to go to any of the amenities but getting into the VRBO was nice and easy after having some communication with the host. I had everything I needed and there was a nice convenient shop if I did miss anything. I’d definitely stay here again."
United States
Tony C.
$320 nightly
The price is $358
Sep 13 - Sep 14
Total with taxes and fees
Sunset and Serenity @ Sailport Tampa

18. Luxury Waterfront Condo with Heated Pool and Balcony

Luxury Waterfront Condo with Heated Pool and Balcony
Rocky Point
9.4 out of 10, Exceptional, (11 reviews)
"Enjoyed the view of the water and the central location."
United States
Wendy S.
$237 nightly
The price is $265
Sep 10 - Sep 11
Total with taxes and fees
Luxury Waterfront Condo with Heated Pool and Balcony

19. Pelican Pointe 418:Walk to Beach~Pool~Free Parking

Pelican Pointe 418:Walk to Beach~Pool~Free Parking
Clearwater Beach
9.6 out of 10, Exceptional, (48 reviews)
"Great time. Location was perfect for walking everywhere. "
United States
Laura M.
$166 nightly
The price is $185
Sep 10 - Sep 11
Total with taxes and fees
Pelican Pointe 418:Walk to Beach~Pool~Free Parking
A beach with clear blue water, a sandy shore, and a few people.

20. 2/2 Penthouse, Clearwater Beach, 801 Avalon!

2/2 Penthouse, Clearwater Beach, 801 Avalon!
Clearwater
9.8 out of 10, Exceptional, (111 reviews)
"The place was clean and great location. Would love to stay again. Perfect"
United States
William M.
$446 nightly
The price is $490
Sep 10 - Sep 11
Total with taxes and fees
2/2 Penthouse, Clearwater Beach, 801 Avalon!
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

CW Resort

CW Resort

10/10 Excellent
"H"
Maikel 2-night trip
Posted 1 hour ago
CW Resort

Find out more about Holiday

Holiday Condo Rentals information

Number of reviews
638
Accommodation
1268 Condo Rentals
Lowest Price
$142
Highest Price
$490

Frequently asked questions

How much do condos in Holiday cost?
Condos in Holiday range from $142 to $490 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 1268 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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