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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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
$579 nightly
The price is $648
Nov 12 - Nov 13
Total with taxes and fees
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.
$246 nightly
The price is $273
Nov 24 - Nov 25
Total with taxes and fees
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.
$285 nightly
The price is $318
Nov 30 - Dec 1
Total with taxes and fees
"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.
$243 nightly
The price is $274
Nov 14 - Nov 15
Total with taxes and fees
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.
$169 nightly
The price is $189
Nov 12 - Nov 13
Total with taxes and fees
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.
$178 nightly
The price is $198
Nov 14 - Nov 15
Total with taxes and fees
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.
$238 nightly
The price is $267
Nov 12 - Nov 13
Total with taxes and fees
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
$316 nightly
The price is $356
Nov 15 - Nov 16
Total with taxes and fees
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.
$170 nightly
The price is $190
Nov 16 - Nov 17
Total with taxes and fees
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
$169 nightly
The price is $189
Nov 15 - Nov 16
Total with taxes and fees
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.
$361 nightly
The price is $400
Nov 16 - Nov 17
Total with taxes and fees
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.
$166 nightly
The price is $186
Nov 17 - Nov 18
Total with taxes and fees
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
$178 nightly
The price is $200
Nov 16 - Nov 17
Total with taxes and fees
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
$355 nightly
The price is $398
Dec 1 - Dec 2
Total with taxes and fees
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
$179 nightly
The price is $201
Nov 16 - Nov 17
Total with taxes and fees
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.
$169 nightly
The price is $189
Nov 15 - Nov 16
Total with taxes and fees
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
$211 nightly
The price is $236
Nov 24 - Nov 25
Total with taxes and fees
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.
$368 nightly
The price is $413
Nov 24 - Nov 25
Total with taxes and fees
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, (233 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.
$271 nightly
The price is $302
Nov 15 - Nov 16
Total with taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
A room with a striped sofa, a wicker chair, a small table, and a ceiling fan.

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.
$177 nightly
The price is $198
Nov 13 - Nov 14
Total with taxes and fees
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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Top Holiday Hotel Reviews

The Westin Tampa Bay

The Westin Tampa Bay

10/10 Excellent
"Clean room was clean. Nice seating area outside by the water for a drink. Parking is $27. Nice location and will return."
Vaughan 2-night trip
Posted 2 hours ago
The Westin Tampa Bay

Find out more about Holiday

Holiday Cottages information

Number of reviews
376
Accommodation
278 Cottages
Lowest Price
$186
Highest Price
$648

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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