Photo by Travel Ginger

Search Cottages in Holiday

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Holiday

3 Mi to Busch Gardens - Vacation Rental in Tampa
Interior

3 Mi to Busch Gardens - Vacation Rental in Tampa

3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved the house, everything was clean and organize. We love the patio and had so much fun playing with the mini golf. "
3 Mi to Busch Gardens - Vacation Rental in Tampa
5 Mi to Beach: Home w/ Pool in Holiday!
Interior

5 Mi to Beach: Home w/ Pool in Holiday!

3.0 star property
5 Mi to Beach: Home w/ Pool in Holiday!
Cozy Crystal Beach Cottage: Walk to Shoreline
Private kitchen

Cozy Crystal Beach Cottage: Walk to Shoreline

3.0 star property
10.0 out of 10, Exceptional, (3)
"This cute cottage has everything you need, and is just one block from the shore. It's located in a quiet beach community and has easy access to Tampa. The early November weather was perfect-- afternoon temps in the low 80s. I would definitely stay here again."
Cozy Crystal Beach Cottage: Walk to Shoreline
Pet-friendly Largo Escape w/ Fire Pit!
Private kitchen

Pet-friendly Largo Escape w/ Fire Pit!

3.0 star property
10.0 out of 10, Exceptional, (1)
Pet-friendly Largo Escape w/ Fire Pit!
5 Mi to Beach: Family-friendly Home in Clearwater!
Interior

5 Mi to Beach: Family-friendly Home in Clearwater!

3.0 star property
9.2 out of 10, Wonderful, (5)
"When we arrived everything was so easy, the check in and when we opened the door we wntered to a very cute lil cozy cottage and it was very clean and the host had all the things you needed for a comfortable stay and more."
5 Mi to Beach: Family-friendly Home in Clearwater!
'sea Turtle Suite' Condo w/ Clearwater Beach Views
Interior

'sea Turtle Suite' Condo w/ Clearwater Beach Views

3.0 star property
8.0 out of 10, Very good, (3)
"We had a great time at Sea Turtle. It was clean and comfortable. Super location -- a few steps to the beach and only a short walk to our favorite bars and restaurants."
'sea Turtle Suite' Condo w/ Clearwater Beach Views
3 Mi to Clearwater Beach: Home w/ Patio & Grill!
Interior

3 Mi to Clearwater Beach: Home w/ Patio & Grill!

3.0 star property
3 Mi to Clearwater Beach: Home w/ Patio & Grill!
'driftwood Beach Suite' - Walk to Clearwater Bch
Interior

'driftwood Beach Suite' - Walk to Clearwater Bch

3.0 star property
'driftwood Beach Suite' - Walk to Clearwater Bch
Vibrant Dunedin Getaway w/ Furnished Patio!
Interior

Vibrant Dunedin Getaway w/ Furnished Patio!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Great property and location. Dunedin cemtre is a 10 min walk from the property. Clean and spacious. Definitely recommend. "
Vibrant Dunedin Getaway w/ Furnished Patio!
Calming Getaway: 9 Mi to Clearwater Beach!
Interior

Calming Getaway: 9 Mi to Clearwater Beach!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The host is very attentive to details. We had more than what we thought. The neighbors were quiet, but friendly once we saw them. The neighborhood overall is calm and clean. Definitely would rebook!"
Calming Getaway: 9 Mi to Clearwater Beach!
12 Mi to Dtwn Tampa: Vibrant Home w/ Outdoor Space
Interior

12 Mi to Dtwn Tampa: Vibrant Home w/ Outdoor Space

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice home "
12 Mi to Dtwn Tampa: Vibrant Home w/ Outdoor Space
Oasis w/ Heated Pool: 5 Mi to Anclote Gulf Park!
Interior

Oasis w/ Heated Pool: 5 Mi to Anclote Gulf Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Nice house. Nicely renovated Clean and comfortable. Management company was easy to work with. Overall great experience. Would stay again if in the area. "
Oasis w/ Heated Pool: 5 Mi to Anclote Gulf Park!
Tampa Home Near Boat Ramp ~ 10 Mi to Dtwn!
Interior

Tampa Home Near Boat Ramp ~ 10 Mi to Dtwn!

3.0 star property
Tampa Home Near Boat Ramp ~ 10 Mi to Dtwn!
Cozy Home in Heart of Tampa w/ Lanai & Pool!
Interior

Cozy Home in Heart of Tampa w/ Lanai & Pool!

3.0 star property
Cozy Home in Heart of Tampa w/ Lanai & Pool!
2 Mi to Beach: Canal-front Home in Hudson!
Interior

2 Mi to Beach: Canal-front Home in Hudson!

3.0 star property
2 Mi to Beach: Canal-front Home in Hudson!
Largo Family Oasis: Private Pool & Hot Tub!
Interior

Largo Family Oasis: Private Pool & Hot Tub!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I like it"
Largo Family Oasis: Private Pool & Hot Tub!
Largo Vacation Rental Home w/ Large Yard!
Interior

Largo Vacation Rental Home w/ Large Yard!

3.0 star property
10.0 out of 10, Exceptional, (3)
"This place was amazing and my kids absolutely loved it! It had everything you needed. My kids were so excited and that confirmed that I chose the right place. "
Largo Vacation Rental Home w/ Large Yard!
Spring Hill Retreat w/ Pool: 7 mi to Weeki Wachee!
Interior

Spring Hill Retreat w/ Pool: 7 mi to Weeki Wachee!

3.0 star property
Spring Hill Retreat w/ Pool: 7 mi to Weeki Wachee!
4 Mi to Dog Beach: Largo Home w/ Pool & Hot Tub!
Interior

4 Mi to Dog Beach: Largo Home w/ Pool & Hot Tub!

3.0 star property
10.0 out of 10, Exceptional, (2)
"It was a very nice little place. Neighbors seemed friendly. Would stay again."
4 Mi to Dog Beach: Largo Home w/ Pool & Hot Tub!
Sunny Hudson Escape w/ Gulf Views & Boat Dock
Interior

Sunny Hudson Escape w/ Gulf Views & Boat Dock

3.0 star property
9.6 out of 10, Exceptional, (5)
"Nice place, quiet…besides every time we cooked the smoke detectors wanted to go off LOL"
Sunny Hudson Escape w/ Gulf Views & Boat Dock
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.
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

SpringHill Suites by Marriott Clearwater Beach

SpringHill Suites by Marriott Clearwater Beach

10/10 Excellent
"Great location just one block from the beach. Really reasonably priced compared to other properties in the area with all the same benefits. Lovey pool with view. Breakfast was excellent. Room clean and comfy."
Anna 2-night trip
Posted 18 hours ago
SpringHill Suites by Marriott Clearwater Beach

Frequently asked questions

Why book your cottage in Holiday with Expedia?
We think that holidays 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.