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Our top choices for Oldsmar cottages
1. 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 tubPalm Harbor
9.8 out of 10, Exceptional, (23 reviews)
"Great place for my wife and I for a weekend getaway. Allison was an attentive host and replied promptly to our needs. Off the beaten path but close to everything, including the beaches. Will stay here again."
Mike C.
The price is CA $147
CA $364 total
includes taxes & fees
Nov 8 - Nov 9
2. Key West Style Cottage - with pool/hot-tub
Key West Style Cottage - with pool/hot-tubDunedin
9.4 out of 10, Exceptional, (36 reviews)
"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
The price is CA $122
CA $265 total
includes taxes & fees
Nov 9 - Nov 10
3. Adorable Waterfront Cottage
Adorable Waterfront CottageOdessa
9.6 out of 10, Exceptional, (29 reviews)
"Awesome stay"
Amber P.
The price is CA $175
CA $369 total
includes taxes & fees
Nov 14 - Nov 15
4. Downtown Dunedin Cozy 1 bedroom Cottage
Downtown Dunedin Cozy 1 bedroom CottageDowntown Dunedin
10.0 out of 10, Exceptional, (46 reviews)
"Best location to enjoy everything in Dunedin with all the things you would need. Lovely cottage!"
Amy H.
The price is CA $168
CA $572 total
includes taxes & fees
Nov 8 - Nov 9
5. Key West Style Cottage - with pool/hot-tub
Key West Style Cottage - with pool/hot-tubDunedin
9.2 out of 10, Wonderful, (39 reviews)
"Great quiet location. Very comfortable"
dan g.
The price is CA $122
CA $265 total
includes taxes & fees
Nov 8 - Nov 9
6. Garden Cottage ,Cozy 2 BR Near Clearwater Beach
Garden Cottage ,Cozy 2 BR Near Clearwater BeachLargo
The price is CA $146
CA $269 total
includes taxes & fees
Nov 16 - Nov 17
7. Key West Style Cottage - with pool/hot-tub
Key West Style Cottage - with pool/hot-tubDunedin
9.8 out of 10, Exceptional, (18 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"
Shane S.
The price is CA $133
CA $278 total
includes taxes & fees
Nov 8 - Nov 9
8. Key West Style Cottage - with pool/hot-tub
Key West Style Cottage - with pool/hot-tubDunedin
9.8 out of 10, Exceptional, (11 reviews)
"Great communication and location is perfect for a quick walk to downtown Dunedin."
Thomas C.
The price is CA $122
CA $267 total
includes taxes & fees
Nov 17 - Nov 18
9. Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near Tampa
Peaceful Lake Retreat • Kayaks + Family Fun • Gated Community Near TampaOdessa
9.6 out of 10, Exceptional, (33 reviews)
"Small, quaint, and very well put together. Everything you will need for a stay in the area"
Jason A.
The price is CA $126
CA $279 total
includes taxes & fees
Nov 10 - Nov 11
10. Key West Style Cottage - with pool/hot-tub
Key West Style Cottage - with pool/hot-tubDunedin
9.6 out of 10, Exceptional, (23 reviews)
"This place was very accommodating, clean and updated like new. The pool was wonderful and grounds were very nice. A short drive (2 min) or 10 min walk to all the restaurants and breweriesWe would definitely stay there again"
Tom D.
The price is CA $122
CA $265 total
includes taxes & fees
Nov 8 - Nov 9
11. Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3Downtown Dunedin
10.0 out of 10, Exceptional, (33 reviews)
"Excellent location. The host pulled out all the stops - they had everything to make the stay amazing!!"
Lori A.
The price is CA $228
CA $497 total
includes taxes & fees
Nov 18 - Nov 19
12. 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, (233 reviews)
"I loved and enjoyed my stay will be booking again. Thank you Mary!"
Amanda
The price is CA $213
CA $423 total
includes taxes & fees
Nov 10 - Nov 11
13. Cozy St Pete Home ~ 2 Mi to Madeira Beach!
Cozy St Pete Home ~ 2 Mi to Madeira Beach!Bay Pines
9.0 out of 10, Wonderful, (2 reviews)
"Very clean comfy sheets and towels"
Anita
The price is CA $117
CA $318 total
includes taxes & fees
Nov 15 - Nov 16
14. Key West Style Cottage - with pool/hot-tub
Key West Style Cottage - with pool/hot-tubDunedin
8.6 out of 10, Excellent, (7 reviews)
"Great place to stay for two!"
Greg F.
The price is CA $122
CA $267 total
includes taxes & fees
Nov 18 - Nov 19
15. Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2Downtown Dunedin
10.0 out of 10, Exceptional, (27 reviews)
"Clean and convenient! Nice getaway spot!"
Drew A.
The price is CA $264
CA $542 total
includes taxes & fees
Nov 24 - Nov 25
16. Cozy Cottage in the heart of St. Pete with hot tub- Pets welcome!
Cozy Cottage in the heart of St. Pete with hot tub- Pets welcome!St. Petersburg
10.0 out of 10, Exceptional, (1 review)
"Great stay, quick uber ride to down town or the airport!"
Georgina G.
The price is CA $112
CA $263 total
includes taxes & fees
Nov 11 - Nov 12
17. Feed Horses at Breakfast - Private Gated Cottage
Feed Horses at Breakfast - Private Gated CottageOdessa
9.8 out of 10, Exceptional, (80 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."
Maria M
The price is CA $201
CA $501 total
includes taxes & fees
Nov 10 - Nov 11
18. Pool Cottage King Suite
Pool Cottage King SuiteClearwater
9.8 out of 10, Exceptional, (11 reviews)
"Very conveniently located to the beach and various restaurants. The room was so beautiful and perfect for mine and my husband’s honeymoon! Very romantic vibes🤗"
Bailey
The price is CA $132
CA $323 total
includes taxes & fees
Nov 24 - Nov 25
19. Stadium Nest /king Bed/ pet friendly
Stadium Nest /king Bed/ pet friendlyPlaza Terrace
10.0 out of 10, Exceptional, (1 review)
"Clean quiet and modern. Well worth the money compared to a hotel. Communication with host was easy and fast. Not sure if items in fridge were complimentary, but if so to the host."
Robert W.
The price is CA $112
CA $222 total
includes taxes & fees
Nov 16 - Nov 17
20. West Riverside Downtown Bungalow
West Riverside Downtown BungalowNorth River
10.0 out of 10, Exceptional, (2 reviews)
"Can’t say enough. Excellent property, excellent and gracious hosts, perfect location. Thank you! We hope to return."
Tamara P.
The price is CA $132
CA $371 total
includes taxes & fees
Nov 11 - Nov 12
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 Oldsmar
Spend a morning watching wildlife at Mobbly Bayou Wilderness Preserve, where kayakers often spot manatees and dolphins. Families flock to Tampa Bay Downs for thrilling horse races or R.E. Olds Park for waterfront picnics and the famous Oldsmar Days festival.
