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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
Oct 3 - Oct 4
Total with taxes and fees
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
A residential property with a garage, a small house with a porch, and a large tree.

2. West Riverside Downtown Bungalow

West Riverside Downtown Bungalow
North River
10.0 out of 10, Exceptional, (1 review)
$213 nightly
The price is $236
Oct 4 - Oct 5
Total with taxes and fees
West Riverside Downtown Bungalow
A small, single-story house with a porch and a screened-in area.

3. 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, (31 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.
$186 nightly
The price is $206
Oct 9 - Oct 10
Total with taxes and fees
Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa
A covered outdoor area with a wooden deck, surrounded by gravel and greenery, overlooking a fenced equestrian area with trees and a clear sky.

4. 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
$331 nightly
The price is $371
Oct 3 - Oct 4
Total with taxes and fees
Cozy Cottage - Close to Everything, Nature Lovers Dream!
A wooden deck with a fire pit and two Adirondack chairs.

5. Adorable Waterfront Cottage

Adorable Waterfront Cottage
Odessa
9.8 out of 10, Exceptional, (27 reviews)
"Awesome stay"
United States
Amber P.
$254 nightly
The price is $285
Oct 3 - Oct 4
Total with taxes and fees
Adorable Waterfront Cottage
A hot tub on a wooden deck with a house in the background.

6. 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.
$236 nightly
The price is $264
Oct 5 - Oct 6
Total with taxes and fees
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (30 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
$175 nightly
The price is $195
Oct 5 - Oct 6
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A museum with a sign reading 'Dunedin History Museum' and two statues in front.

8. Adorable Villa 1 min to Downtown Dunedin

Adorable Villa 1 min to Downtown Dunedin
Dunedin
10.0 out of 10, Exceptional, (13 reviews)
"Darling clean villa. Great location that is walking distance to shops and restaurants. Additional towels would be helpful. We would stay here again."
United States
Kris H.
$234 nightly
The price is $261
Oct 12 - Oct 13
Total with taxes and fees
Adorable Villa 1 min to Downtown Dunedin
A two-story house with a covered patio, a fenced yard, and a tree in the foreground.

9. Downtown Dunedin Cozy 1 bedroom Cottage

Downtown Dunedin Cozy 1 bedroom Cottage
Downtown Dunedin
10.0 out of 10, Exceptional, (44 reviews)
"Jennifer was among the most responsive hosts I've ever encountered and accommodating to no end."
United States
Grant N.
$367 nightly
The price is $405
Oct 10 - Oct 11
Total with taxes and fees
Downtown Dunedin Cozy 1 bedroom Cottage
A modern kitchen with a stainless steel refrigerator, a wooden ceiling fan, and a striped sofa with decorative pillows.

10. 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, (228 reviews)
"I loved and enjoyed my stay will be booking again. Thank you Mary!"
United States
Amanda
$227 nightly
The price is $253
Oct 4 - Oct 5
Total with taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
10.0 out of 10, Exceptional, (9 reviews)
"Great communication and location is perfect for a quick walk to downtown Dunedin."
United States
Thomas C.
$175 nightly
The price is $195
Oct 11 - Oct 12
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A covered outdoor seating area with a view of the beach and ocean.

12. 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.
$300 nightly
The price is $335
Oct 12 - Oct 13
Total with taxes and fees
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1
A poolside area with lounge chairs, a small pool, and a covered patio.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (38 reviews)
"Great quiet location. Very comfortable"
United States
dan g.
$175 nightly
The price is $195
Oct 5 - Oct 6
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.

14. 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, (173 reviews)
"Perfect location for the beach and restaurants. "
United States
Heather S.
$248 nightly
The price is $276
Oct 7 - Oct 8
Total with taxes and fees
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
A two-story house with a covered porch, a front door, and a small outdoor seating area with chairs.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.6 out of 10, Exceptional, (19 reviews)
"Easy access and a lot of amenities."
United States
Scott H.
$174 nightly
The price is $194
Oct 4 - Oct 5
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.

16. 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.
$314 nightly
The price is $350
Oct 27 - Oct 28
Total with taxes and fees
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
A covered outdoor seating area with a view of the beach and ocean.

17. 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.
$305 nightly
The price is $340
Oct 14 - Oct 15
Total with taxes and fees
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
An outdoor patio area with a dining table, chairs, and potted plants.

18. 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
6.0 out of 10, (1 review)
"Let me start by saying we were very excited to stay near the beach and the place is within walking distance which was great. As soon as we arrived to our cottage they were workers putting bricks for the days we were day which was very dusty noise and we couldn't sit to relax in the back their was no jacuzzi and are car was blocked from the workers not once did she come to say hi or sto see if we needed anything wouldn't not come here and inside i was cut with nails .light switch were missing...
United States
Otilia G.
$165 nightly
The price is $184
Oct 5 - Oct 6
Total with taxes and fees
Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub
A single-story house with a front porch, a small deck, and a pathway leading to the entrance.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.8 out of 10, Exceptional, (17 reviews)
"Perfect stay at this cozy cottage. Peaceful, quiet and clean. Will definitely be returning when we are back in the area. The location was great and we walked everywhere"
United States
Shane S.
$183 nightly
The price is $204
Oct 4 - Oct 5
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.

20. 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.
$174 nightly
The price is $194
Oct 4 - Oct 5
Total with taxes and fees
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

Fairfield Inn & Suites by Marriott Clearwater Beach

Fairfield Inn & Suites by Marriott Clearwater Beach

10/10 Excellent
"Everything was awesome! We loved our stay except the valet service which was a bit much."
Sandhya 1-night trip
Posted less than an hour ago
Fairfield Inn & Suites by Marriott Clearwater Beach

Find out more about Holiday

Holiday Cottages information

Number of reviews
609
Accommodation
278 Cottages
Lowest Price
$184
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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