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 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

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 20 - Oct 21
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, (2 reviews)
"Can’t say enough. Excellent property, excellent and gracious hosts, perfect location. Thank you! We hope to return."
United States
Tamara P.
$243 nightly
The price is $269
Oct 20 - Oct 21
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 Restaurant/bars, park.

"The Salty Lime" Walk to Restaurant/bars, park.
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.
$309 nightly
The price is $342
Oct 20 - Oct 21
Total with taxes and fees
"The Salty Lime" Walk to Restaurant/bars, park.
A small, single-story house with a porch and a screened-in area.

4. 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)
"Small, quaint, and very well put together. Everything you will need for a stay in the area"
United States
Jason A.
$186 nightly
The price is $206
Oct 20 - Oct 21
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.

5. 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.
$237 nightly
The price is $264
Oct 21 - Oct 22
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.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (32 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
$174 nightly
The price is $194
Oct 25 - Oct 26
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, (78 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 24 - Oct 25
Total with taxes and fees
Feed Horses at Breakfast - Private Gated Cottage
A wooden deck with a fire pit and two Adirondack chairs.

8. Adorable Waterfront Cottage

Adorable Waterfront Cottage
Odessa
9.8 out of 10, Exceptional, (27 reviews)
"Awesome stay"
United States
Amber P.
$255 nightly
The price is $286
Oct 21 - Oct 22
Total with taxes and fees
Adorable Waterfront Cottage
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.
$346 nightly
The price is $381
Oct 25 - Oct 26
Total with taxes and fees
Downtown Dunedin Cozy 1 bedroom Cottage
A poolside area with lounge chairs, a small pool, and a covered patio.

10. 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.
$174 nightly
The price is $194
Oct 25 - Oct 26
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.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.6 out of 10, Exceptional, (10 reviews)
"Great communication and location is perfect for a quick walk to downtown Dunedin."
United States
Thomas C.
$174 nightly
The price is $194
Oct 26 - Oct 27
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A two-story house with a covered porch, a front door, and a small outdoor seating area with chairs.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.6 out of 10, Exceptional, (22 reviews)
"Easy access and a lot of amenities."
United States
Scott H.
$174 nightly
The price is $194
Oct 26 - Oct 27
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.

13. 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, (26 reviews)
"Clean and convenient! Nice getaway spot!"
United States
Drew A.
$346 nightly
The price is $386
Nov 10 - Nov 11
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.

14. 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, (229 reviews)
"I loved and enjoyed my stay will be booking again. Thank you Mary!"
United States
Amanda
$220 nightly
The price is $245
Oct 20 - Oct 21
Total with taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
A covered outdoor seating area with a view of the beach and 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.
$302 nightly
The price is $337
Oct 20 - Oct 21
Total with taxes and fees
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1
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, (33 reviews)
"Excellent location. The host pulled out all the stops - they had everything to make the stay amazing!!"
United States
Lori A.
$289 nightly
The price is $324
Oct 20 - Oct 21
Total with taxes and fees
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
A covered patio area with a wooden pergola, a dining table with chairs, a surfboard, and a colorful rug.

17. 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, (176 reviews)
"Perfect location for the beach and restaurants. "
United States
Heather S.
$243 nightly
The price is $271
Oct 20 - Oct 21
Total with taxes and fees
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
A residential property with a brick exterior, a wooden fence, and a landscaped garden with plants and a pathway.

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)
$160 nightly
The price is $177
Oct 20 - Oct 21
Total with taxes and fees
Private Lutz Studio Near Tampa Outlets – Patio & Full Kitchen
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

19. 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 25 - Oct 26
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
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, (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 20 - Oct 21
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

Sailport Waterfront Suites

Sailport Waterfront Suites

10/10 Excellent
"Great property. Great location. Friendly Staff"
Michael Wade 6-night trip
Posted 3 hours ago
Sailport Waterfront Suites

Find out more about Holiday

Holiday Cottages information

Number of reviews
818
Accommodation
278 Cottages
Lowest Price
$177
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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