Holiday Cottages

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

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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

Tahitian Development

includes taxes & fees

19 Nov - 20 Nov

A residential property with a garage, a small house with a porch, and a large tree.

2. West Riverside Downtown Bungalow

North River

Tamara P.

includes taxes & fees

11 Nov - 12 Nov

A single-story house with a green exterior, a concrete driveway, and a white garage door.

3. "The Salty Lime" Walk to Restaurant/bars, park.

Port Richey

Theresa B.

includes taxes & fees

30 Nov - 1 Dec

A hot tub on a wooden deck with a house in the background.

4. Enchanting cottage with AC in Palm Harbor - 2 bedrooms, 1 bathroom & hot tub

Palm Harbor

Mike C.

includes taxes & fees

8 Nov - 9 Nov

A small, single-story house with a porch and a screened-in area.

5. Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa

Odessa

Jason A.

includes taxes & fees

16 Nov - 17 Nov

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

Dunedin

"Had an amazing stay at this beautiful cottage! The place was very clean, spacious, and comfortable, making it the perfect spot to relax and enjoy our time away. I felt safe throughout the stay, and the location was excellent, with cafés and restaurants within walking distance. The host was wonderful (very easy to communicate back and forth with, even left an itinerary with recommendations, LOVEDDD THATTT) and truly, appreciated the opportunity to stay here. Would absolutely recommend this...

Nayeli

includes taxes & fees

9 Nov - 10 Nov

A wooden deck with a fire pit and two Adirondack chairs.

7. Adorable Waterfront Cottage

Odessa

Amber P.

includes taxes & fees

6 Nov - 7 Nov

A covered outdoor area with a wooden deck, surrounded by gravel and greenery, overlooking a fenced equestrian area with trees and a clear sky.

8. Feed Horses at Breakfast - Private Gated Cottage

Odessa

Maria M

includes taxes & fees

9 Nov - 10 Nov

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

Amy H.

includes taxes & fees

8 Nov - 9 Nov

A poolside area with lounge chairs, a small pool, and a covered patio.

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

Dunedin

dan g.

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a stainless steel refrigerator, a wooden ceiling fan, and a striped sofa with decorative pillows.

11. The Purple Flower - 30 Second walk to the Beach. Free parking.

Clearwater

Amanda

includes taxes & fees

22 Nov - 23 Nov

A single-story house with a white garage, a front door, and a small porch.

12. Garden Cottage ,Cozy 2 BR Near Clearwater Beach

Largo

includes taxes & fees

15 Nov - 16 Nov

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

Dunedin

Thomas C.

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a covered porch, a front door, and a small outdoor seating area with chairs.

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

Dunedin

Tom D.

includes taxes & fees

8 Nov - 9 Nov

A balcony with wicker furniture, a small round table, and two bottles of Corona Extra.

15. Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3

Downtown Dunedin

Lori A.

includes taxes & fees

1 Dec - 2 Dec

A single-story house with a front porch, a small deck, and a pathway leading to the entrance.

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

Dunedin

Shane S.

includes taxes & fees

15 Nov - 16 Nov

A waterfront patio with red seating and palm trees.

17. Pool Cottage King Suite

Clearwater

Bailey

includes taxes & fees

18 Nov - 19 Nov

A two-story house with a front porch, a mailbox, and a tree in the front yard.

18. No Damage Walk to Downtown Dunedin and Waterfront Yard Pets OK Barefoot Parrot 2

Downtown Dunedin

Drew A.

includes taxes & fees

24 Nov - 25 Nov

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

Dunedin

Greg F.

includes taxes & fees

9 Nov - 10 Nov

An indoor swimming pool with a water feature, surrounded by palm trees and ambient lighting.

20. Blue Cottage STEPS to beach DOG friendly Sleeps 5 FULL Beach Gear Hot Tub

Clearwater

Darrick J.

includes taxes & fees

13 Nov - 14 Nov

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Top Holiday Hotel Reviews

Sailport Waterfront Suites

10/10 Excellent

"Great all around"

Country Inn & Suites by Radisson, Tampa Airport North, FL

10/10 Excellent

"The staff here is super friendly!! The hotel was very clean and well maintained. My room was clean and the bed and pillows are were very comfortable. The breakfast and shuttle are definite wonderful perks! This is one of my top choices whenever I visit MT. Stefanie was super friendly and always greeted me with a smile! Thank you for the friendly conversation on the way to the airport! ☺️"

Pelican Pointe Clearwater Beach Hotel

8/10 Good

"I’ve stayed here twice now with my boyfriend, and for the price, I think it’s completely worth it! The location is amazing, with just a short walk to the beach and tons of great restaurants and bars nearby. The heated pool is really nice, and there’s plenty of outdoor seating to relax and hang out. One thing I will say is that the outdoor areas aren’t very private, and it’s pretty easy for anyone to just walk onto the property. However, I felt completely safe both times we stayed and was never worried about it! The bathrooms were also pretty small in both rooms we stayed in, but that’s something I can overlook considering how affordable it is. Both times, the rooms were very clean inside, which is always a plus! The outside of the property could definitely use a good power wash and a little more upkeep, but overall, we’ve had great experiences here. If you’re looking for somewhere affordable, clean, and within walking distance of everything, I definitely recommend it! I would stay here again!! Also recommend Sea-Guiene(idk how to spell it) for a nicer dinner, went like four times and was always amazing!!"

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