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 red pathway leading to the entrance, a garage door, and a small porch area.

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 15 - Nov 16
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.
$242 nightly
The price is $269
Nov 30 - Dec 1
Total with taxes and fees
West Riverside Downtown Bungalow
A building with a red roof and a sign that reads "CATCHES".

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.
$294 nightly
The price is $327
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 15 - Nov 16
Total with taxes and fees
Adorable Waterfront Cottage
A small, single-story house with a porch and a screened-in area.

5. 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.
$187 nightly
The price is $208
Nov 15 - Nov 16
Total with taxes and fees
Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

6. 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 covered outdoor area with a wooden deck, surrounded by gravel and greenery, overlooking a fenced equestrian area with trees and a clear sky.

7. 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
Property grounds

8. Charming Tampa Cottage - Full Kitchen, Parking, Wifi

Charming Tampa Cottage - Full Kitchen, Parking, Wifi
Lowry Park Central
10.0 out of 10, Exceptional, (26 reviews)
"Great and easy stay!"
United States
Katie R.
Charming Tampa Cottage - Full Kitchen, Parking, Wifi
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 tropical-themed rental property with a thatched-roof hut, a wooden signboard, and a small outdoor seating area.

10. TIKI Cottage Sleeps 6 STEPS to Beach Hot Tub Dog Friendly FULL Beach Gear

TIKI Cottage Sleeps 6 STEPS to Beach Hot Tub Dog Friendly FULL Beach Gear
Clearwater
$271 nightly
The price is $304
Nov 18 - Nov 19
Total with taxes and fees
TIKI Cottage Sleeps 6 STEPS to Beach Hot Tub Dog Friendly FULL Beach Gear
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 central entrance, surrounded by well-maintained landscaping and palm trees.

12. 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 15 - Nov 16
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 small, single-story building with a white door and a sign that reads 'Corner Cottage.'

14. 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.
$178 nightly
The price is $199
Dec 2 - Dec 3
Total with taxes and fees
Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub
A waterfront patio with red seating and palm trees.

15. Pool Cottage King Suite

Pool Cottage King Suite
Clearwater
9.8 out of 10, Exceptional, (12 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 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
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 covered outdoor seating area with a thatched roof, overlooking a beach with surfboards and a distant island.

17. 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
$332 nightly
The price is $372
Dec 1 - Dec 2
Total with taxes and fees
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
A residential backyard with a wooden fence, a white garage, and a garden with plants and a birdbath.

18. Private Lutz Studio Near Tampa Outlets – Patio & Full Kitchen

Private Lutz Studio Near Tampa Outlets – Patio & Full Kitchen
Lutz
10.0 out of 10, Exceptional, (1 review)
$152 nightly
The price is $169
Nov 27 - Nov 28
Total with taxes and fees
Private Lutz Studio Near Tampa Outlets – Patio & Full Kitchen
A patio with a table and chairs, a grill, and potted plants.

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)
"Wonderful stay !"
United States
Rhonda C.
$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 covered patio area with a wooden pergola, a dining table with chairs, a surfboard, and a colorful rug.

20. Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Clearwater
10.0 out of 10, Exceptional, (181 reviews)
"Loved our stay, had everything we needed for a quick weekend getaway!"
United States
Ryleigh G.
$292 nightly
The price is $325
Nov 15 - Nov 16
Total with taxes and fees
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
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

Pelican Pointe Clearwater Beach Hotel

Pelican Pointe Clearwater Beach Hotel

10/10 Excellent
"Nice ròms. Ample parking. Across the street from the beach. Nice heated pool. Great place!"
DAVID 7-night trip
Posted 4 hours ago
Pelican Pointe Clearwater Beach Hotel

Find out more about Holiday

Holiday Cottages information

Number of reviews
753
Accommodation
278 Cottages
Lowest Price
$169
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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