Holiday Homes in Dunedin

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Our top choices for Dunedin holiday homes

1. Charming Bungalow Downtown

Charming Bungalow Downtown
Dunedin
9.6 out of 10, Exceptional, (46 reviews)
"Cutest cottage! Great decor and bed is comfy. Very convenient to downtown. Very clean and laundry is a bonus. Host was responsive to any concerns."
United States
Melodie J.
The price is NZ$453
includes taxes & fees
8 Nov - 9 Nov
Charming Bungalow Downtown

2. Walk Downtown & Waterfront | Dunedin's Best Street

Walk Downtown & Waterfront | Dunedin's Best Street
Downtown Dunedin
The price is NZ$619
includes taxes & fees
10 Nov - 11 Nov
Walk Downtown & Waterfront | Dunedin's Best Street

3. Downtown Dunedin 2026 Golf Cart & Bikes!

Downtown Dunedin 2026 Golf Cart & Bikes!
Dunedin
10.0 out of 10, Exceptional, (2 reviews)
"As soon as we opened the door it felt like our own cozy home. It had everything we needed with a great location for walkers or cyclists and very dog friendly. Beautiful …loved the decorating."
United States
Maurice C.
The price is NZ$629
includes taxes & fees
9 Nov - 10 Nov
Downtown Dunedin 2026 Golf Cart & Bikes!

4. Downtown Dunedin, Golf Cart, King bed + Bunk room

Downtown Dunedin, Golf Cart, King bed + Bunk room
Dunedin
The price is NZ$670
includes taxes & fees
8 Nov - 9 Nov
Downtown Dunedin, Golf Cart, King bed + Bunk room

5. No Hurricane Damage Walk to Downtown Dunedin and Waterfront Private Home for 8

No Hurricane Damage Walk to Downtown Dunedin and Waterfront Private Home for 8
Downtown Dunedin
10.0 out of 10, Exceptional, (75 reviews)
"Great house with amazing location in downtown Dunedin"
United States
Doug H.
The price is NZ$832
includes taxes & fees
9 Nov - 10 Nov
No Hurricane Damage Walk to Downtown Dunedin and Waterfront Private Home for 8

6. Coastal Retreat in Downtown Dunedin w/ Yard+Grill

Coastal Retreat in Downtown Dunedin w/ Yard+Grill
Dunedin
10.0 out of 10, Exceptional, (5 reviews)
"Lisa was great and was a great stay!"
United States
Scott M.
The price is NZ$706
includes taxes & fees
8 Nov - 9 Nov
Coastal Retreat in Downtown Dunedin w/ Yard+Grill

7. Downtown Gem w/Fenced Yard & Grill - Main St

Downtown Gem w/Fenced Yard & Grill - Main St
Dunedin
10.0 out of 10, Exceptional, (9 reviews)
"Wondering place to stay "
United States
Debbie D.
Downtown Gem w/Fenced Yard & Grill - Main St

8. Dunedin's Finest St - Walk Downtown & Waterfront - Palms Cottage

Dunedin's Finest St - Walk Downtown & Waterfront - Palms Cottage
Dunedin
The price is NZ$689
includes taxes & fees
10 Nov - 11 Nov
Dunedin's Finest St - Walk Downtown & Waterfront - Palms Cottage

9. Heated Pool, Hot Tub, Bikes, Minutes to Clearwater Beach & Honeymoon Island!

Heated Pool, Hot Tub, Bikes, Minutes to Clearwater Beach & Honeymoon Island!
Barrington Hills
9.6 out of 10, Exceptional, (18 reviews)
"This property is amazing! Privacy with the pool was exactly what we needed! Aleksandra was incredibly helpful and responsive. I would definitely see staying here again "
United States
Danielle H.
The price is NZ$1,252
includes taxes & fees
13 Nov - 14 Nov
Heated Pool, Hot Tub, Bikes, Minutes to Clearwater Beach & Honeymoon Island!

10. Dunedin 3BR/2.5BA | Private Pool & Game Room

Dunedin 3BR/2.5BA | Private Pool & Game Room
Barrington Hills
8.8 out of 10, Excellent, (6 reviews)
"Host was welcoming. Instructions were great. Communications were excellent. Accommodations were excellent for seven adults and two frenchies. We had plenty of space. Great location. The handyman, Matt, did a great job fixing three issues immediately. Highly recommend this rental!!! "
United States
Jennifer O.
The price is NZ$1,435
includes taxes & fees
9 Nov - 10 Nov
Dunedin 3BR/2.5BA | Private Pool & Game Room

11. 2 Homes- Heated Pool & Pickleball- The Dunedin Duo

2 Homes- Heated Pool & Pickleball- The Dunedin Duo
Dunedin, Florida
9.2 out of 10, Wonderful, (18 reviews)
"Nice property, huge space which was critical for 6 grown men who didn’t want to share hotel rooms. Easy checkin, clear communication, convenient to everything."
United States
Patrick V.
The price is NZ$1,617
includes taxes & fees
8 Nov - 9 Nov
2 Homes- Heated Pool & Pickleball- The Dunedin Duo

12. New Upscale Retreat Downtown Dunedin w/ Balcony! Sleeps 4

New Upscale Retreat Downtown Dunedin w/ Balcony! Sleeps 4
Dunedin
10.0 out of 10, Exceptional, (7 reviews)
"Everything was great! Communication, cleanliness and amenities were excellent."
United States
Thomas A.
New Upscale Retreat Downtown Dunedin w/ Balcony! Sleeps 4

13. Private Tropical Oasis in Coastal Paradise W fenced yard.

Private Tropical Oasis in Coastal Paradise W fenced yard.
Spring Branch
9.0 out of 10, Wonderful, (50 reviews)
"Very clean,easy check in and very quiet and secluded"
United States
Marcos S.
The price is NZ$280
includes taxes & fees
3 Dec - 4 Dec
Private Tropical Oasis in Coastal Paradise W fenced yard.

14. "Romantic home with a hot tub, 10 minutes from Clearwater Beach

"Romantic home with a hot tub, 10 minutes from Clearwater Beach
Clearwater
9.8 out of 10, Exceptional, (21 reviews)
"Hot tub was very nice and so was my host. would definitely book again if im in the area!"
United States
richard s.
The price is NZ$382
includes taxes & fees
11 Nov - 12 Nov
"Romantic home with a hot tub, 10 minutes from Clearwater Beach

15. Private Oasis! Luxury King Bed! Walk To Restaurants!

Private Oasis! Luxury King Bed! Walk To Restaurants!
Downtown Palm Harbor
9.6 out of 10, Exceptional, (18 reviews)
"The host was very welcoming! The VRBO was clean, well-equipped, and in a great location for our needs. "
United States
Michael l.
The price is NZ$562
includes taxes & fees
30 Nov - 1 Dec
Private Oasis! Luxury King Bed! Walk To Restaurants!

16. Palm Harbor Paradise | Spacious Home with Pool & Hot Tub

Palm Harbor Paradise | Spacious Home with Pool & Hot Tub
Pipers Meadow
9.0 out of 10, Wonderful, (135 reviews)
"Everything was great, the neighborhood is quiet and beautiful, a little ways away from shops and beaches "
United States
Allyssa P.
The price is NZ$1,157
includes taxes & fees
15 Nov - 16 Nov
Palm Harbor Paradise | Spacious Home with Pool & Hot Tub

17. Florida Retro Home minutes from the famous Clearwater Beach and Honeymoon Island

Florida Retro Home minutes from the famous Clearwater Beach and Honeymoon Island
Clearwater
10.0 out of 10, Exceptional, (38 reviews)
"Excellent hospitality and superb decor! My family and I really enjoyed our trip! Highly recommended!!!!"
United States
Laura
The price is NZ$854
includes taxes & fees
11 Nov - 12 Nov
Florida Retro Home minutes from the famous Clearwater Beach and Honeymoon Island

18. Crystal Beach Cozy Cottage - Your Perfect Vacation Escape!

Crystal Beach Cozy Cottage - Your Perfect Vacation Escape!
Palm Harbor
10.0 out of 10, Exceptional, (68 reviews)
"We had an amazing stay! The property was perfect for our family and the host was very nice and communicative!"
United States
Corena F.
The price is NZ$571
includes taxes & fees
22 Nov - 23 Nov
Crystal Beach Cozy Cottage - Your Perfect Vacation Escape!

19. Beautiful Remodeled House - Outdoor Pool & screened Florida Room

Beautiful Remodeled House - Outdoor Pool & screened Florida Room
Clearwater
9.8 out of 10, Exceptional, (83 reviews)
"Good value location near tampa"
United States
Ryan S.
The price is NZ$804
includes taxes & fees
11 Nov - 12 Nov
Beautiful Remodeled House - Outdoor Pool & screened Florida Room

20. 'Sea Turtle Suite' Condo w/ Clearwater Beach Views

'Sea Turtle Suite' Condo w/ Clearwater Beach Views
Clearwater Beach
9.4 out of 10, Exceptional, (128 reviews)
"Great location!"
United States
Teagan N.
The price is NZ$763
includes taxes & fees
8 Nov - 9 Nov
'Sea Turtle Suite' Condo w/ Clearwater Beach Views
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.

Learn more about Dunedin

Stroll along the waterfront, catching a Blue Jays game at the stadium or exploring the marina's charm. Hop over to Honeymoon Island for world-class beaches, then return to sample local brews in this walkable coastal gem.

An aerial view of a coastal island with clear turquoise waters, sandy beaches, and lush greenery.

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