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 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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
$606 nightly
The price is $679
Aug 23 - Aug 24
Total with taxes and fees
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach

2. 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
$187 nightly
The price is $208
Aug 23 - Aug 24
Total with taxes and fees
Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub

3. Lemon Cottage Steps to Beach Dog Friendly Hot Tub Full Beach Gear

Lemon Cottage Steps to Beach Dog Friendly Hot Tub Full Beach Gear
Clearwater
$213 nightly
The price is $237
Aug 24 - Aug 25
Total with taxes and fees
Lemon Cottage Steps to Beach Dog Friendly Hot Tub Full Beach Gear

4. Pineapple Cottage STEPS to beach dog friendly FULL Beach Gear Hot Tub

Pineapple Cottage STEPS to beach dog friendly FULL Beach Gear Hot Tub
Clearwater
$240 nightly
The price is $267
Aug 23 - Aug 24
Total with taxes and fees
Pineapple Cottage STEPS to beach dog friendly FULL Beach Gear Hot Tub
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, (30 reviews)
"Great Property. Clean, safe, peaceful. Good Location with lots to do. Would defiantly stay there again on future visits. Hosts were the best, great communication."
United States
Eric M.
$187 nightly
The price is $207
Aug 23 - Aug 24
Total with taxes and fees
Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa
A two-story house with a porch, a staircase, and a small garden with palm trees.

6. Tarpon Tides Cottage - Walk to the Sponge Docks & Downtown!

Tarpon Tides Cottage - Walk to the Sponge Docks & Downtown!
Tarpon Springs Greektown Historic District
10.0 out of 10, Exceptional, (32 reviews)
"Great property in a great location. Host was very attentive and checked in often. Would definitely stay here again "
United States
Kim S.
$409 nightly
The price is $455
Aug 24 - Aug 25
Total with taxes and fees
Tarpon Tides Cottage - Walk to the Sponge Docks & Downtown!
A residential property with a garage, a small house with a porch, and a large tree.

7. West Riverside Downtown Bungalow

West Riverside Downtown Bungalow
North River
10.0 out of 10, Exceptional, (1 review)
$219 nightly
The price is $242
Aug 24 - Aug 25
Total with taxes and fees
West Riverside Downtown Bungalow
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. Cozy Cottage - Close to Everything, Nature Lovers Dream!

Cozy Cottage - Close to Everything, Nature Lovers Dream!
Odessa
9.8 out of 10, Exceptional, (77 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
$335 nightly
The price is $375
Aug 23 - Aug 24
Total with taxes and fees
Cozy Cottage - Close to Everything, Nature Lovers Dream!
A building with a red roof and a sign that reads "CATCHES".

9. "The Salty Lime" Walk to Restaurant/bars, park.

"The Salty Lime" Walk to Restaurant/bars, park.
Port Richey
10.0 out of 10, Exceptional, (2 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 Salty Lime" Walk to Restaurant/bars, park.
A wooden deck with a fire pit and two Adirondack chairs.

10. Adorable Waterfront Cottage

Adorable Waterfront Cottage
Odessa
9.8 out of 10, Exceptional, (26 reviews)
"Clean room, cold A/C, attentive and kind host, beautiful location, very accomodating"
United States
Brian J.
$257 nightly
The price is $288
Aug 27 - Aug 28
Total with taxes and fees
Adorable Waterfront Cottage
A residential property with a brick exterior, a wooden fence, and a landscaped garden with plants and a pathway.

11. The White Door Studio.

The White Door Studio.
Lutz
10.0 out of 10, Exceptional, (1 review)
$135 nightly
The price is $149
Aug 24 - Aug 25
Total with taxes and fees
The White Door Studio.
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
9.4 out of 10, Exceptional, (29 reviews)
"It was perfect for what we needed. It was clean and maintained well. Great location close to the heart of town."
United States
Sean
$183 nightly
The price is $204
Aug 23 - Aug 24
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A museum with a brick facade, large windows, and a covered entrance.

13. Cozy Cottage in the Heart of Dunedin

Cozy Cottage in the Heart of Dunedin
Dunedin
9.8 out of 10, Exceptional, (17 reviews)
"Great location, walk to shops and restaurants. Cottage is very cozy and cute with everything you need."
United States
Laura S.
$224 nightly
The price is $249
Sep 13 - Sep 14
Total with taxes and fees
Cozy Cottage in the Heart of Dunedin
A modern kitchen with stainless steel appliances, a central island with bar stools, and pendant lighting.

14. Amazing cottage in sunny Tampa close to everything.

Amazing cottage in sunny Tampa close to everything.
Lowry Park Central
10.0 out of 10, Exceptional, (1 review)
"Great stay! "
United States
Maggie R.
$285 nightly
The price is $319
Aug 23 - Aug 24
Total with taxes and fees
Amazing cottage in sunny Tampa close to everything.
A covered outdoor seating area with wooden chairs and tables, overlooking a beach with surfboards and a clear view of the ocean.

15. Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1

Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1
Downtown Dunedin
10.0 out of 10, Exceptional, (18 reviews)
"Great location, easy walk to all the fun stuff. "
United States
Patrick G.
$321 nightly
The price is $358
Aug 26 - Aug 27
Total with taxes and fees
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1
A covered outdoor seating area with wooden chairs and tables, overlooking a beach with surfboards and a clear view of the ocean.

16. 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, (23 reviews)
"Great place, walking distance to everything! Highly recommend!"
United States
David R.
$306 nightly
The price is $342
Sep 7 - Sep 8
Total with taxes and fees
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.6 out of 10, Exceptional, (18 reviews)
"The location and cottage were great! Quiet area"
United States
Thomas W.
$174 nightly
The price is $194
Aug 24 - Aug 25
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.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
10.0 out of 10, Exceptional, (7 reviews)
"In the heart of Dunedin. Clean and lovely place to stay. Met all our needs. "
United States
sharon h.
$174 nightly
The price is $194
Aug 23 - Aug 24
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A poolside area with lounge chairs, a small pool, and a covered patio.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.2 out of 10, Wonderful, (37 reviews)
"Walkable to downtown and a great chicken place called Jardin de Pollo that is super close! Pool area was relaxing and I enjoyed that there was a designated lot to park that was not street parking. "
United States
Gianna
$183 nightly
The price is $204
Aug 25 - Aug 26
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
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
9.8 out of 10, Exceptional, (170 reviews)
"Perfect location for the beach and restaurants. "
United States
Heather S.
$241 nightly
The price is $269
Sep 1 - Sep 2
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

Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

10/10 Excellent
"Excellent breakfast compared to other hotels, always fresh and clean. Food was simple but excellent. The rooms were super clean and staff was always helpful with anything you needed."
Jose 3-night trip
Posted 3 hours ago
Fairfield Inn & Suites by Marriott Clearwater Beach

Find out more about Holiday

Holiday Cottages information

Number of reviews
450
Accommodation
264 Cottages
Lowest Price
$149
Highest Price
$679

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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