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

Search Holiday Cottages

Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

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
Sep 2 - Sep 3
Total with taxes and fees
Lakefront Anglers Oasis in Holiday! 8 Mi to Beach
A two-story house with a porch, a staircase, and a small garden with palm trees.

2. 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.
$400 nightly
The price is $445
Sep 5 - Sep 6
Total with taxes and fees
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.

3. West Riverside Downtown Bungalow

West Riverside Downtown Bungalow
North River
10.0 out of 10, Exceptional, (1 review)
$220 nightly
The price is $243
Sep 2 - Sep 3
Total with taxes and fees
West Riverside Downtown Bungalow
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, (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.
$189 nightly
The price is $209
Sep 8 - Sep 9
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)
"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.
$271 nightly
The price is $302
Sep 2 - Sep 3
Total with taxes and fees
Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & 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.

6. 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
$335 nightly
The price is $375
Sep 2 - Sep 3
Total with taxes and fees
Cozy Cottage - Close to Everything, Nature Lovers Dream!
A wooden deck with a fire pit and two Adirondack chairs.

7. Adorable Waterfront Cottage

Adorable Waterfront Cottage
Odessa
9.8 out of 10, Exceptional, (27 reviews)
"Awesome stay"
United States
Amber P.
$257 nightly
The price is $288
Sep 2 - Sep 3
Total with taxes and fees
Adorable Waterfront Cottage
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

8. 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
$175 nightly
The price is $195
Sep 2 - Sep 3
Total with taxes and fees
Key West Style Cottage - with pool/hot-tub
A museum with a brick facade, large windows, and a covered entrance.

9. 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
Sep 26 - Sep 27
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.

10. Downtown Dunedin Cozy 1 bedroom Cottage

Downtown Dunedin Cozy 1 bedroom Cottage
Downtown Dunedin
10.0 out of 10, Exceptional, (42 reviews)
"The cottage has everything we needed. The location was great! We could walk everywhere for shops and restaurants which were very dog friendly. We loved the Pinellas trail. "
United States
carol l.
$349 nightly
The price is $384
Sep 8 - Sep 9
Total with taxes and fees
Downtown Dunedin Cozy 1 bedroom Cottage
A covered outdoor seating area with wooden chairs and tables, overlooking a beach with surfboards and a clear view of the ocean.

11. 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.
$304 nightly
The price is $339
Sep 2 - Sep 3
Total with taxes and fees
Rave Reviews Walk to Downtown Dunedin & Waterfront Pets Ok -Barefoot Parrot 1
A museum with a brick facade, large windows, and a covered entrance.

12. Cozy Cottage in the Heart of Dunedin

Cozy Cottage in the Heart of Dunedin
Dunedin
9.8 out of 10, Exceptional, (18 reviews)
"Great location, walk to shops and restaurants. Cottage is very cozy and cute with everything you need."
United States
Laura S.
$228 nightly
The price is $253
Sep 13 - Sep 14
Total with taxes and fees
Cozy Cottage in the Heart of Dunedin
A covered outdoor seating area with wooden chairs and tables, overlooking a beach with surfboards and a clear view of the 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, (25 reviews)
"Clean and convenient! Nice getaway spot!"
United States
Drew A.
$317 nightly
The price is $353
Sep 2 - Sep 3
Total with taxes and fees
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.

14. 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.
$304 nightly
The price is $339
Sep 2 - Sep 3
Total with taxes and fees
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
A residential property with a brick exterior, a wooden fence, and a landscaped garden with plants and a pathway.

15. The White Door Studio.

The White Door Studio.
Lutz
10.0 out of 10, Exceptional, (1 review)
$135 nightly
The price is $149
Sep 2 - Sep 3
Total with taxes and fees
The White Door Studio.
A poolside area with lounge chairs, a small pool, and a covered patio.

16. 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)
"Great quiet location. Very comfortable"
United States
dan g.
$175 nightly
The price is $195
Sep 2 - Sep 3
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
9.8 out of 10, Exceptional, (170 reviews)
"Perfect location for the beach and restaurants. "
United States
Heather S.
$241 nightly
The price is $268
Sep 8 - Sep 9
Total with taxes and fees
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
A two-story building with a blue and white color scheme, a central entrance with a door, and a covered porch area.

18. 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)
"The property was amazing. We spent the days exploring the area and spent the evenings at the pool and then sitting on the porch relaxing. Hosts were very helpful with suggestions about places to visit and places to eat. I can’t wait to come back and stay again!"
United States
Kim G.
$175 nightly
The price is $195
Sep 2 - Sep 3
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.

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

Key West Style Cottage - with pool/hot-tub
Dunedin
9.8 out of 10, Exceptional, (16 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.
$190 nightly
The price is $212
Sep 2 - Sep 3
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.
$184 nightly
The price is $205
Sep 2 - Sep 3
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

The Westin Tampa Bay

The Westin Tampa Bay

10/10 Excellent
"Stunning rooms."
Destiny 3-night trip
Posted 1 hour ago
The Westin Tampa Bay

Find out more about Holiday

Holiday Cottages information

Number of reviews
541
Accommodation
264 Cottages
Lowest Price
$149
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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