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Check prices for these dates

Next weekend
6 Jun - 8 Jun
In two weeks
13 Jun - 15 Jun
In one month
27 Jun - 29 Jun
In two months
25 Jul - 27 Jul

Compare 506 Cottages in Oldsmar with updated reviews, rates, and availability.

Private family waterfront beach cottage. Best location step out to bay and gulf
On the beach

Private family waterfront beach cottage. Best location step out to bay and gulf

9.0 out of 10, Wonderful, (89)
"Very cute and quaint quite cottage "
The price is AED 926
AED 1,975 total
includes taxes & fees
30 May - 31 May
Private family waterfront beach cottage. Best location step out to bay and gulf
Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach
A heated pool

Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach

9.4 out of 10, Exceptional, (16)
"This is my second time staying here. Very clean, well kept property. Quiet neighborhood, walking distance to beach and restaurants. "
Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach
Cozy Cottage Near Downtown + Waterfront
Beach

Cozy Cottage Near Downtown + Waterfront

9.8 out of 10, Exceptional, (49)
"Very clean. Great location. Walkable to so many restaurants and the Pinellas trail. Loved our stay."
Cozy Cottage Near Downtown + Waterfront
Beautiful luxury 2 bedroom private Cottage
Outdoor pool

Beautiful luxury 2 bedroom private Cottage

10.0 out of 10, Exceptional, (19)
"Beautiful cottage. Very clean. The grounds were incredible. Close to downtown and parks. "
Beautiful luxury 2 bedroom private Cottage
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Beach nearby, sun loungers, beach towels

Sleeps 6 Daily Rentals, Pets OK, Hot Tub

8.4 out of 10, Very Good, (51)
"Nice beach house"
The price is AED 493
AED 1,293 total
includes taxes & fees
4 Jun - 5 Jun
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV
Interior

Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV

9.8 out of 10, Exceptional, (189)
"Perfect spot for our little family! We really enjoyed our stay!"
Best deal on the beach/sleeps 6/All New/Gulf views!/55 inch TV
The Purple Flower - 30 Second walk to the Beach. Free parking.
Outdoor dining

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

9.8 out of 10, Exceptional, (179)
"Adorable lil place. Will definitely be coming back again!"
The Purple Flower - 30 Second walk to the Beach. Free parking.
Historic Beach Cottage steps from beach. Pet friendly!
On the beach, sun loungers, beach towels

Historic Beach Cottage steps from beach. Pet friendly!

9.2 out of 10, Wonderful, (119)
"Front door not secure. "
The price is AED 856
AED 1,792 total
includes taxes & fees
2 Jun - 3 Jun
Historic Beach Cottage steps from beach. Pet friendly!
COZY COTTAGE ON PRIVATE BEACH *CLEARWATER/BELLEAIR BEACH
Property grounds

COZY COTTAGE ON PRIVATE BEACH *CLEARWATER/BELLEAIR BEACH

9.6 out of 10, Exceptional, (55)
"Location can't be beat - area is safe, beach is literally 50 steps out the door, house was clean and very comfortable. Everything needed was provided and owner was totally available if needed. Would stay here again if returning to this same area - very relaxing trip! "
COZY COTTAGE ON PRIVATE BEACH *CLEARWATER/BELLEAIR BEACH
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer
On the beach

Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer

8.0 out of 10, Very Good, (91)
"Clean, excellent communication with property manager! Needs a little love but the beach views can’t be beat! Highly recommend! "
The price is AED 1,639
AED 3,196 total
includes taxes & fees
28 Jun - 29 Jun
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer
BANANA BREEZE COTTAGE. Steps away from the beach Heated pool.
Outdoor pool, a heated pool

BANANA BREEZE COTTAGE. Steps away from the beach Heated pool.

9.8 out of 10, Exceptional, (50)
"We really enjoyed our stay and would recommend it to our friends and family "
BANANA BREEZE COTTAGE. Steps away from the beach Heated pool.
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool
On the beach

Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool

9.8 out of 10, Exceptional, (55)
"Perfect beach house for a single family! The kids loved the convenience of being on the beach and the heated pool. "
Yachtsman*OCEAN FRONT COTTAGE*Right on the sand*sleeps up to 6*Heated Pool
Quaint bungalow just off Main Street Last Minute openings!
Exterior

Quaint bungalow just off Main Street Last Minute openings!

9.2 out of 10, Wonderful, (29)
"This was the cutest house right in the middle of Downtown Dunedin. Will definitely book again! "
Quaint bungalow just off Main Street Last Minute openings!
****Tropical Coquina Cove Studio #3 Heated POOL . 5 Min walk to Beach ****
A heated pool, sun loungers

****Tropical Coquina Cove Studio #3 Heated POOL . 5 Min walk to Beach ****

9.8 out of 10, Exceptional, (28)
"Quiet, clean, spacious room with a well stocked kitchen. Clean pool, just a short block walk to the beach. We had a wonderful time, definitely recommend this. Great value!"
****Tropical Coquina Cove Studio #3 Heated POOL . 5 Min walk to Beach ****
Cozy and roomy cottage
Outdoor pool

Cozy and roomy cottage

10.0 out of 10, Exceptional, (47)
"Fabulous!! Have stayed here several times. Already planning another trip!!"
Cozy and roomy cottage
Adorable Waterfront Cottage
Property grounds

Adorable Waterfront Cottage

9.8 out of 10, Exceptional, (16)
"Michael’s place was great and he was super accommodating! "
The price is AED 437
AED 993 total
includes taxes & fees
30 May - 31 May
Adorable Waterfront Cottage
Historic Tarpon Springs Abode ~ 3 Mi to Beach
Fridge, microwave, stovetop, dishwasher

Historic Tarpon Springs Abode ~ 3 Mi to Beach

10.0 out of 10, Exceptional, (35)
"House and location were great!"
Historic Tarpon Springs Abode ~ 3 Mi to Beach
Coral Cottage pool/gas firepit a 2 bedr 2 bath sleeps 6
Outdoor pool

Coral Cottage pool/gas firepit a 2 bedr 2 bath sleeps 6

10.0 out of 10, Exceptional, (36)
"The house was just as advertised and was a great location for all of the traveling we did during our stay. The access to highways was quite easy and the neighborhood was very quiet. The house was clean and spacious. We would definitely recommend this house."
Coral Cottage pool/gas firepit a 2 bedr 2 bath sleeps 6
Grove Keeper Cottage unit has a tree house atmosphere
Property grounds

Grove Keeper Cottage unit has a tree house atmosphere

10.0 out of 10, Exceptional, (36)
"The property was beautiful and quiet. It was close to nice restaurants and the art gallery. I would stay again if going to that area. Thank you!"
Grove Keeper Cottage unit has a tree house atmosphere
The Briny Bubble…Charming 2-bedroom cottage in Dunedin, steps to Main Street
Fridge, microwave, oven, stovetop

The Briny Bubble…Charming 2-bedroom cottage in Dunedin, steps to Main Street

10.0 out of 10, Exceptional, (6)
"We had a great stay. The house is wonderful and walking distance to the heart of downtown Dunedin."
The Briny Bubble…Charming 2-bedroom cottage in Dunedin, steps to Main Street
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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Other property types in Oldsmar

Sailport Waterfront Suites
Beach nearby, beach volleyball, fishing

Sailport Waterfront Suites

3.5 star property
8.2 out of 10, Very Good, (4535)
"This is a very nice resort. We really enjoyed our stay."
The price is AED 382
AED 496 total
includes taxes & fees
1 Jun - 2 Jun
Sailport Waterfront Suites
Sunset Vistas Two Bedroom Beachfront Suites
Aerial view

Sunset Vistas Two Bedroom Beachfront Suites

3.5 star property
8.8 out of 10, Excellent, (3224)
"Friendly staff near beach great stay "
The price is AED 806
AED 1,003 total
includes taxes & fees
1 Jun - 2 Jun
Sunset Vistas Two Bedroom Beachfront Suites
Mint House St. Petersburg - Downtown
Standard Studio, Kitchen, Corner | Terrace/patio

Mint House St. Petersburg - Downtown

4.5 star property
9.4 out of 10, Exceptional, (622)
"A great location, lovely poolside room and well appointed amenities inside the room."
The price is AED 423
AED 478 total
includes taxes & fees
15 Jun - 16 Jun
Mint House St. Petersburg - Downtown
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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