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 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

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 27 - Oct 28
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.
$245 nightly
The price is $271
Oct 27 - Oct 28
Total with taxes and fees
West Riverside Downtown Bungalow
A hot tub on a wooden deck with a house in the background.

3. 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.
$235 nightly
The price is $262
Oct 27 - Oct 28
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.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (35 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
$173 nightly
The price is $193
Oct 28 - Oct 29
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
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 27 - Oct 28
Total with taxes and fees
Adorable Waterfront Cottage
A covered outdoor area with a wooden deck, surrounded by gravel and greenery, overlooking a fenced equestrian area with trees and a clear sky.

6. 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
$331 nightly
The price is $371
Oct 27 - Oct 28
Total with taxes and fees
Feed Horses at Breakfast - Private Gated Cottage
A two-story house with a covered patio, a fenced yard, and a tree in the foreground.

7. Downtown Dunedin Cozy 1 bedroom Cottage

Downtown Dunedin Cozy 1 bedroom Cottage
Downtown Dunedin
10.0 out of 10, Exceptional, (45 reviews)
"Jennifer was among the most responsive hosts I've ever encountered and accommodating to no end."
United States
Grant N.
$350 nightly
The price is $387
Oct 28 - Oct 29
Total with taxes and fees
Downtown Dunedin Cozy 1 bedroom Cottage
A balcony with wicker furniture, a small round table, and two bottles of Corona Extra.

8. 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.
$288 nightly
The price is $323
Oct 28 - Oct 29
Total with taxes and fees
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
A waterfront patio with red seating and palm trees.

9. Pool Cottage King Suite

Pool Cottage King Suite
Clearwater
9.8 out of 10, Exceptional, (11 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 $235
Nov 4 - Nov 5
Total with taxes and fees
Pool Cottage King Suite
A modern kitchen with white cabinetry, a central island with stools, and a dark blue sofa in the living area.

10. 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 27 - Oct 28
Total with taxes and fees
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1
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
9.8 out of 10, Exceptional, (11 reviews)
"Great communication and location is perfect for a quick walk to downtown Dunedin."
United States
Thomas C.
$173 nightly
The price is $193
Oct 27 - Oct 28
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.

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.
$174 nightly
The price is $194
Nov 1 - Nov 2
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.

13. 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.
$173 nightly
The price is $193
Oct 27 - Oct 28
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
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, (231 reviews)
"I loved and enjoyed my stay will be booking again. Thank you Mary!"
United States
Amanda
$235 nightly
The price is $262
Nov 5 - Nov 6
Total with taxes and fees
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.

15. 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.
$182 nightly
The price is $203
Oct 27 - Oct 28
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.

16. 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.
$173 nightly
The price is $193
Oct 27 - Oct 28
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.

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, (179 reviews)
"Perfect location for the beach and restaurants. "
United States
Heather S.
$271 nightly
The price is $302
Oct 29 - Oct 30
Total with taxes and fees
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
A two-story house with a front porch, a mailbox, and a tree in the front yard.

18. 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.
$341 nightly
The price is $380
Nov 10 - Nov 11
Total with taxes and fees
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
An indoor swimming pool with a water feature, surrounded by palm trees and ambient lighting.

19. 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.
$185 nightly
The price is $206
Nov 8 - Nov 9
Total with taxes and fees
Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub
A residential property with a brick exterior, a wooden fence, and a landscaped garden with plants and a pathway.

20. 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 27 - Oct 28
Total with taxes and fees
Private Lutz Studio Near Tampa Outlets – Patio & Full Kitchen
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

Gulfview Hotel on the Beach

Gulfview Hotel on the Beach

10/10 Excellent
"Stay here quite often, the stafff are always so friendly and accommodating ( know some by name) and within walking distance to everything, great view too!!!"
Becca 4-night trip
Posted less than an hour ago
Gulfview Hotel on the Beach

Find out more about Holiday

Holiday Cottages information

Number of reviews
759
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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