A beach with people standing and facing the ocean, with their arms raised. There are two suitcases on the sand.

Search Holiday Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Holiday cottages

House (4 Bedrooms) | Interior

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 5 - Aug 6
Total with taxes and fees
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
Exterior

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, (29 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.
$226 nightly
The price is $250
Aug 7 - Aug 8
Total with taxes and fees
Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa
Exterior

3. 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 5 - Aug 6
Total with taxes and fees
West Riverside Downtown Bungalow
Property grounds

4. The White Door Studio.

The White Door Studio.
Lutz
10.0 out of 10, Exceptional, (1 review)
$140 nightly
The price is $154
Aug 12 - Aug 13
Total with taxes and fees
The White Door Studio.
Smart TV

5. Eco-Friendly Charming Tampa Cottage - Full Kitchen, Parking, Wifi

Eco-Friendly Charming Tampa Cottage - Full Kitchen, Parking, Wifi
Lowry Park Central
10.0 out of 10, Exceptional, (22 reviews)
"We had a nice stay! Place was just right for us clean, Quiet, close to everything! "
United States
Donna S.
$135 nightly
The price is $150
Aug 7 - Aug 8
Total with taxes and fees
Eco-Friendly Charming Tampa Cottage - Full Kitchen, Parking, Wifi
Exterior

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, (30 reviews)
"Great property in a great location. Host was very attentive and checked in often. Would definitely stay here again "
United States
Kim S.
$414 nightly
The price is $462
Aug 5 - Aug 6
Total with taxes and fees
Tarpon Tides Cottage - Walk to the Sponge Docks & Downtown!
Terrace/patio

7. 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
Aug 5 - Aug 6
Total with taxes and fees
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Property grounds

8. 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.
$254 nightly
The price is $285
Aug 5 - Aug 6
Total with taxes and fees
Adorable Waterfront Cottage
Outdoor spa tub

9. 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.
$277 nightly
The price is $308
Aug 5 - Aug 6
Total with taxes and fees
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub
Exterior

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.4 out of 10, Exceptional, (28 reviews)
"Great value and location! "
United States
Robert G.
$181 nightly
The price is $202
Aug 7 - Aug 8
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
Private kitchen

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.
$281 nightly
The price is $315
Aug 5 - Aug 6
Total with taxes and fees
Amazing cottage in sunny Tampa close to everything.
Exterior

12. Walkable Dog Friendly Cottage Downtown

Walkable Dog Friendly Cottage Downtown
Dunedin
10.0 out of 10, Exceptional, (39 reviews)
"Pet friendly, clean, beautiful space. "
United States
Peter M.
$285 nightly
The price is $318
Aug 6 - Aug 7
Total with taxes and fees
Walkable Dog Friendly Cottage Downtown
Pool

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.6 out of 10, Exceptional, (17 reviews)
"The location and cottage were great! Quiet area"
United States
Thomas W.
$174 nightly
The price is $194
Aug 10 - Aug 11
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
Outdoor pool

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.2 out of 10, Wonderful, (34 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
$174 nightly
The price is $194
Aug 5 - Aug 6
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
Exterior

15. 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 5 - Aug 6
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
Property grounds

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.
$315 nightly
The price is $351
Aug 16 - Aug 17
Total with taxes and fees
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
Terrace/patio

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
9.8 out of 10, Exceptional, (168 reviews)
"Perfect location for the beach and restaurants. "
United States
Heather S.
$245 nightly
The price is $273
Aug 5 - Aug 6
Total with taxes and fees
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Flat-screen TV, Netflix, Hulu, streaming services

18. 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, (218 reviews)
"I loved and enjoyed my stay will be booking again. Thank you Mary!"
United States
Amanda
$249 nightly
The price is $278
Aug 11 - Aug 12
Total with taxes and fees
The Purple Flower - 30 Second walk to the Beach. Free parking.
Exterior

19. 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
$221 nightly
The price is $246
Aug 5 - Aug 6
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
Exterior

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.
$198 nightly
The price is $221
Aug 8 - Aug 9
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Holiday Hotel Reviews

Sailport Waterfront Suites

Sailport Waterfront Suites

8/10 Good
"I asked for a late check out and was told they would leave notes for the person in the morning. Found out from the manager in the morning they were completely booked and couldn't accommodate me. I was out to lunch with my family and they wanted us out by 1. I felt like I was being interrogated because the manager asked how was I at lunch if I just spoke with house keeping and she kept asking if I knew who I spoke to the night before. I never got the other person's name and didn't think I had to. When I went to check out the manager that was rude and unprofessional seemed very eager to tell me that the person I spoke to the night before was the night manager. That is very concerning to me that two managers treated a customer that way. If it was their mistake they should've figured something out. We had to leave at 2 pm and our flight was not until 7:30! Our vacation turned nightmare because of two "managers" that have zero customer service experience. I would recommend retraining or possibly new managers. The restaurant staff were amazing, the woman that checked us in was friendly and helpful , security and maintenance crew were awesome! But unfortunately we will not book there again due to the managers."
Ana 6-night trip
Posted 4 hours ago
Sailport Waterfront Suites

Find out more about Holiday

Holiday Cottages information

Number of reviews
734
Accommodation
264 Cottages
Lowest Price
$150
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.

Explore a world of travel with Expedia