Photo by Jignesh Patel

Search Holiday Cottage Rentals from CA $122

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Check prices for these dates

Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29
In one month
Dec 11 - Dec 13
In two months
Jan 8 - Jan 10

Our top choices for Holiday cottages

A single-story house with a garage, a covered porch, and a well-maintained lawn.

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 CA $385
CA $915 total
includes taxes & fees
Nov 13 - Nov 14
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
A wooden deck with two Adirondack chairs facing a body of water, surrounded by a white fence and palm trees.

2. West Riverside Downtown Bungalow

West Riverside Downtown Bungalow
North River
10.0 out of 10, Exceptional, (2 reviews)
"Can’t say enough. Excellent property, excellent and gracious hosts, perfect location. Thank you! We hope to return."
United States
Tamara P.
The price is CA $142
CA $386 total
includes taxes & fees
Dec 9 - Dec 10
West Riverside Downtown Bungalow
A single-story house with a green exterior, a concrete driveway, and a white garage door.

3. "The Salty Lime" Walk to Restaurants.

"The Salty Lime" Walk to Restaurants.
Port Richey
10.0 out of 10, Exceptional, (3 reviews)
"So well stocked! Thank you, James. We so enjoyed our stay. We two octogenarians loved this place; spotless, super equipped and tasteful. Outside patio was perfect.Nice job, James!"
United States
Theresa B.
The price is CA $130
CA $465 total
includes taxes & fees
Nov 30 - Dec 1
"The Salty Lime" Walk to Restaurants.
A wooden deck with a fire pit and two Adirondack chairs.

4. Adorable Waterfront Cottage

Adorable Waterfront Cottage
Odessa
9.6 out of 10, Exceptional, (29 reviews)
"Awesome stay"
United States
Amber P.
The price is CA $177
CA $388 total
includes taxes & fees
Nov 15 - Nov 16
Adorable Waterfront Cottage
A poolside area with lounge chairs, a small pool, and a covered patio.

5. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.2 out of 10, Wonderful, (39 reviews)
"Great quiet location. Very comfortable"
United States
dan g.
The price is CA $123
CA $267 total
includes taxes & fees
Nov 15 - Nov 16
Key West Style Cottage - with pool/hot-tub
A small, single-story house with a porch and a screened-in area.

6. Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa

Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa
Odessa
9.6 out of 10, Exceptional, (33 reviews)
"Great property in a cute gated community!"
United States
Taylor S.
The price is CA $127
CA $281 total
includes taxes & fees
Nov 15 - Nov 16
Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa
A hot tub on a wooden deck with a house in the background.

7. Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub

Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
Palm Harbor
9.8 out of 10, Exceptional, (23 reviews)
"Great place for my wife and I for a weekend getaway. Allison was an attentive host and replied promptly to our needs. Off the beaten path but close to everything, including the beaches. Will stay here again."
United States
Mike C.
The price is CA $158
CA $379 total
includes taxes & fees
Nov 12 - Nov 13
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
A covered outdoor area with a wooden deck, surrounded by gravel and greenery, overlooking a fenced equestrian area with trees and a clear sky.

8. Feed Horses at Breakfast - Private Gated Cottage

Feed Horses at Breakfast - Private Gated Cottage
Odessa
9.8 out of 10, Exceptional, (80 reviews)
"We love ❤️!!!!! This place! I recommend and I will use definitely again. I love Mango and Bubble, our neighbors, and the clean and cozy plus also so quite. Thank you again for let us stay in this beautiful place."
United States
Maria M
The price is CA $202
CA $505 total
includes taxes & fees
Nov 15 - Nov 16
Feed Horses at Breakfast - Private Gated Cottage
A two-story house with a covered porch, a front door, and a small outdoor seating area with chairs.

9. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.6 out of 10, Exceptional, (23 reviews)
"This place was very accommodating, clean and updated like new. The pool was wonderful and grounds were very nice. A short drive (2 min) or 10 min walk to all the restaurants and breweriesWe would definitely stay there again"
United States
Tom D.
The price is CA $123
CA $267 total
includes taxes & fees
Nov 17 - Nov 18
Key West Style Cottage - with pool/hot-tub
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

10. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (36 reviews)
"Had an amazing stay at this beautiful cottage! The place was very clean, spacious, and comfortable, making it the perfect spot to relax and enjoy our time away. I felt safe throughout the stay, and the location was excellent, with cafés and restaurants within walking distance. The host was wonderful (very easy to communicate back and forth with, even left an itinerary with recommendations, LOVEDDD THATTT) and truly, appreciated the opportunity to stay here. Would absolutely recommend this...
United States
Nayeli
The price is CA $123
CA $267 total
includes taxes & fees
Nov 15 - Nov 16
Key West Style Cottage - with pool/hot-tub
A two-story house with a covered patio, a fenced yard, and a tree in the foreground.

11. Downtown Dunedin Cozy 1 bedroom Cottage

Downtown Dunedin Cozy 1 bedroom Cottage
Downtown Dunedin
10.0 out of 10, Exceptional, (46 reviews)
"Best location to enjoy everything in Dunedin with all the things you would need. Lovely cottage!"
United States
Amy H.
The price is CA $162
CA $566 total
includes taxes & fees
Nov 16 - Nov 17
Downtown Dunedin Cozy 1 bedroom Cottage
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

12. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.8 out of 10, Exceptional, (11 reviews)
"Great communication and location is perfect for a quick walk to downtown Dunedin."
United States
Thomas C.
The price is CA $123
CA $269 total
includes taxes & fees
Dec 1 - Dec 2
Key West Style Cottage - with pool/hot-tub
A single-story house with a white garage, a front door, and a small porch.

13. Garden Cottage ,Cozy 2 BR Near Clearwater Beach

Garden Cottage ,Cozy 2 BR Near Clearwater Beach
Largo
The price is CA $147
CA $279 total
includes taxes & fees
Nov 16 - Nov 17
Garden Cottage ,Cozy 2 BR Near Clearwater Beach
A balcony with wicker furniture, a small round table, and two bottles of Corona Extra.

14. Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3

Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
Downtown Dunedin
10.0 out of 10, Exceptional, (34 reviews)
"Great location (30 sec walk to Dunedin Brewery!) to downtown and waterfront. Communication with Jen was ongoing and timely. While we did not spend alot of time in the unit, we enjoyed our stay and would recommend!"
Canada
Michelle
The price is CA $287
CA $571 total
includes taxes & fees
Dec 1 - Dec 2
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
A single-story house with a front porch, a small deck, and a pathway leading to the entrance.

15. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
9.8 out of 10, Exceptional, (19 reviews)
"Great stay and located close to downtown."
United States
Michael
The price is CA $134
CA $280 total
includes taxes & fees
Nov 17 - Nov 18
Key West Style Cottage - with pool/hot-tub
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

16. Key West Style Cottage - with pool/hot-tub

Key West Style Cottage - with pool/hot-tub
Dunedin
8.6 out of 10, Excellent, (7 reviews)
"Great place to stay for two!"
United States
Greg F.
The price is CA $123
CA $267 total
includes taxes & fees
Nov 15 - Nov 16
Key West Style Cottage - with pool/hot-tub
A waterfront patio with red seating and palm trees.

17. Pool Cottage King Suite

Pool Cottage King Suite
Clearwater
9.8 out of 10, Exceptional, (11 reviews)
"Very conveniently located to the beach and various restaurants. The room was so beautiful and perfect for mine and my husband’s honeymoon! Very romantic vibes🤗"
United States
Bailey
The price is CA $133
CA $334 total
includes taxes & fees
Nov 24 - Nov 25
Pool Cottage King Suite
A two-story house with a front porch, a mailbox, and a tree in the front yard.

18. Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2

Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
Downtown Dunedin
10.0 out of 10, Exceptional, (27 reviews)
"Clean and convenient! Nice getaway spot!"
United States
Drew A.
The price is CA $309
CA $599 total
includes taxes & fees
Nov 24 - Nov 25
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
A modern kitchen with a stainless steel refrigerator, a wooden ceiling fan, and a striped sofa with decorative pillows.

19. The Purple Flower - 30 Second walk to the Beach. Free parking.

The Purple Flower - 30 Second walk to the Beach. Free parking.
Clearwater
9.8 out of 10, Exceptional, (234 reviews)
"We could not have asked for a better location. So close to the beach, and we enjoyed walking to restaurants and Shipwrecked. Great place!"
United States
Sara S.
The price is CA $215
CA $426 total
includes taxes & fees
Nov 15 - Nov 16
The Purple Flower - 30 Second walk to the Beach. Free parking.
A beach scene with a cart loaded with items, including a blue bag, a pink bag, and a blue water bottle.

20. Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub

Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub
Clearwater
6.8 out of 10, (3 reviews)
"New management is friendly and onsite. Great improvement"
United States
Darrick J.
The price is CA $189
CA $279 total
includes taxes & fees
Nov 13 - Nov 14
Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub
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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Learn more about Holiday

Nestled along the Gulf Coast, this relaxed town offers pristine beaches and the stunning Anclote River Park for kayaking adventures. Locals recommend exploring the Suncoast Trail by bike and timing your visit to Holiday's lively seasonal festivals where seafood is always the star.

See all hotels in Holiday
A calm lake with a dock, a boat, and a building surrounded by trees.
Photo by Jignesh Patel
Open Photo by Jignesh Patel

Frequently Asked Questions

Why book your cottage in Holiday with Expedia?

We think that vacations should be a walk in the park, so if you're on the lookout for cottages in Holiday at the perfect price, Expedia has got your back. Keep the budget under control and stay in an economical option surrounded by wilderness, or splurge on an upmarket cottage to spoil your loved ones.

How can I find cheap cottages in Holiday?

The simplest way to spot cheap cottages in Holiday is with Expedia's handy filter tool. Narrow your search results by star rating, amenities and budget to access unbeatable rates with only a few clicks.

What is there to do in Holiday near my cottage?

After you've settled into your hotel, set out and explore the cool things Holiday has to offer. Anclote River Park is a top attraction to add to your must-do list.

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