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 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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 $378
CA $941 total
includes taxes & fees
Aug 30 - Aug 31
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
A small, single-story house with a porch and a screened-in area.

2. 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)
"The hosts were so responsive and helpful during our stay. The bed was super comfy and the house was stocked with anything one may need. I would recommend this place to anyone in the Odessa area."
United States
Hannah P.
The price is CA $125
CA $285 total
includes taxes & fees
Aug 31 - Sep 1
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.

3. 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.
The price is CA $213
CA $613 total
includes taxes & fees
Sep 20 - Sep 21
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.

4. West Riverside Downtown Bungalow

West Riverside Downtown Bungalow
North River
10.0 out of 10, Exceptional, (1 review)
The price is CA $128
CA $331 total
includes taxes & fees
Aug 30 - Aug 31
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.

5. 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
The price is CA $198
CA $518 total
includes taxes & fees
Aug 30 - Aug 31
Cozy Cottage - Close to Everything, Nature Lovers Dream!
A wooden deck with a fire pit and two Adirondack chairs.

6. Adorable Waterfront Cottage

Adorable Waterfront Cottage
Odessa
9.8 out of 10, Exceptional, (26 reviews)
"Awesome stay"
United States
Amber P.
The price is CA $173
CA $395 total
includes taxes & fees
Aug 31 - Sep 1
Adorable Waterfront Cottage
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)
"Our host was excellent! Very responsive to all of our requests! The Enchanting cottage was perfect for us! All of the appliances were brand new, the shower was great and the bed was comfortable! We enjoyed the deck and privacy! A peaceful quiet retreat, and close to lots of things to do! "
United States
Kathy D.
The price is CA $176
CA $416 total
includes taxes & fees
Aug 30 - Aug 31
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
A residential property with a brick exterior, a wooden fence, and a landscaped garden with plants and a pathway.

8. The White Door Studio.

The White Door Studio.
Lutz
10.0 out of 10, Exceptional, (1 review)
The price is CA $111
CA $207 total
includes taxes & fees
Sep 2 - Sep 3
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.

9. 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
The price is CA $126
CA $280 total
includes taxes & fees
Aug 30 - Aug 31
Key West Style Cottage - with pool/hot-tub
A museum with a brick facade, large windows, and a covered entrance.

10. 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.
The price is CA $110
CA $346 total
includes taxes & fees
Sep 13 - Sep 14
Cozy Cottage in the Heart of Dunedin
A modern kitchen with stainless steel appliances, a central island with bar stools, and pendant lighting.

11. 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.
The price is CA $208
CA $439 total
includes taxes & fees
Aug 31 - Sep 1
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.

12. 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, (25 reviews)
"Clean and convenient! Nice getaway spot!"
United States
Drew A.
The price is CA $205
CA $486 total
includes taxes & fees
Aug 30 - Aug 31
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
A wooden deck with metal chairs, a thatched roof, and a view of the sea.

13. 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, (32 reviews)
"Places to eat very close a within waljing distance."
United States
Ellen W.
The price is CA $190
CA $468 total
includes taxes & fees
Aug 30 - Aug 31
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
A covered outdoor seating area with wooden chairs and tables, overlooking a beach with surfboards and a clear view of the ocean.

14. 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.
The price is CA $190
CA $468 total
includes taxes & fees
Sep 1 - Sep 2
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1

15. 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.
The price is CA $115
CA $267 total
includes taxes & fees
Aug 30 - Aug 31
Key West Style Cottage - with pool/hot-tub
A hotel room with a large bed, two bedside tables with lamps, a black leather chair, and a window with blinds.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
10.0 out of 10, Exceptional, (8 reviews)
"In the heart of Dunedin. Clean and lovely place to stay. Met all our needs. "
United States
sharon h.
The price is CA $115
CA $267 total
includes taxes & fees
Sep 1 - Sep 2
Key West Style Cottage - with pool/hot-tub
A poolside area with lounge chairs, a small pool, and a covered patio.

17. 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
The price is CA $126
CA $280 total
includes taxes & fees
Aug 30 - Aug 31
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.

18. 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.
The price is CA $174
CA $369 total
includes taxes & fees
Sep 1 - Sep 2
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
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, (223 reviews)
"I loved and enjoyed my stay will be booking again. Thank you Mary!"
United States
Amanda
The price is CA $175
CA $370 total
includes taxes & fees
Sep 1 - Sep 2
The Purple Flower - 30 Second walk to the Beach. Free parking.
A single-story house with a front porch, a small deck, and a pathway leading to the entrance.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.8 out of 10, Exceptional, (15 reviews)
"Great stay and located close to downtown."
United States
Michael
The price is CA $172
CA $337 total
includes taxes & fees
Aug 30 - Aug 31
Key West Style Cottage - with pool/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

AC Hotel Clearwater Beach

AC Hotel Clearwater Beach

10/10 Excellent
"I found the hotel to be excellent. Not one complaint. Highly recommend"
Erin 1-night trip
Posted 2 hours ago
AC Hotel Clearwater Beach

Find out more about Holiday

Holiday Cottages information

Number of reviews
736
Accommodation
264 Cottages
Lowest Price
CA $209
Highest Price
CA $941

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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