Search Cottages in Oldsmar

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Check prices for these dates

Next weekend
23 May - 25 May
In two weeks
30 May - 1 Jun
In one month
13 Jun - 15 Jun
In two months
11 Jul - 13 Jul

Compare 495 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, (87)
"Very cute and quaint quite cottage "
The price is AED 1,034
AED 2,079 total
includes taxes & fees
26 May - 27 May
Private family waterfront beach cottage. Best location step out to bay and gulf
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, (178)
"Adorable lil place. Will definitely be coming back again!"
The price is AED 400
AED 904 total
includes taxes & fees
14 May - 15 May
The Purple Flower - 30 Second walk to the Beach. Free parking.
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Fridge, microwave, oven, stovetop

Cozy Cottage - Close to Everything, Nature Lovers Dream!

10.0 out of 10, Exceptional, (54)
"It really was a cozy place to stay."
The price is AED 584
AED 1,435 total
includes taxes & fees
14 May - 15 May
Cozy Cottage - Close to Everything, Nature Lovers Dream!
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
Fridge, microwave, oven, stovetop

Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!

10.0 out of 10, Exceptional, (131)
"Great stay and close to the sugar sand beach. Mary our host was great. I would recommend staying there."
Cute and Cozy Beach Bungalow. Steps to the Beach. Free off-street Parking!
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Beach nearby, sun loungers, beach towels

White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

9.6 out of 10, Exceptional, (103)
"This was our 2nd time staying at the Egret cottage and we had a lovely stay. House is just as it’s pictured. Clean and comfortable. The location is great. Close to the beach yet away from the crowds."
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Downtown Dunedin Cottage Near Beaches + Breweries
Beach

Downtown Dunedin Cottage Near Beaches + Breweries

10.0 out of 10, Exceptional, (58)
"Everything was perfect. Great little place with a good location."
Downtown Dunedin Cottage Near Beaches + Breweries
50 Steps to Beach, Family Friendly, Heated Pool
Aerial view

50 Steps to Beach, Family Friendly, Heated Pool

2.0 star property
10.0 out of 10, Exceptional, (7)
"Grace was very responsive as a host. The cottage was clean and had everything we needed. Just steps to the beach. Walking distance to restaurants. Will be returning next year! I wish I could keep this place a secret! It’s that good."
50 Steps to Beach, Family Friendly, Heated Pool
Canary Beach Cottage - steps to the sand!
Aerial view

Canary Beach Cottage - steps to the sand!

9.8 out of 10, Exceptional, (42)
"Had a great time. The cottage was perfect for the two of us! We especially liked the easy access to the beach!"
Canary Beach Cottage - steps to the sand!
NEW! Indian Rocks Beach Cottage Steps from Ocean!
On the beach

NEW! Indian Rocks Beach Cottage Steps from Ocean!

9.8 out of 10, Exceptional, (53)
"Very clean and well stocked with everything you need for a comfortable stay! Loved the decor, very "homey". Property is just off the beach and close to local amenities."
NEW! Indian Rocks Beach Cottage Steps from Ocean!
Frenchy's Cottage 490 in Clearwater Beach
Aerial view

Frenchy's Cottage 490 in Clearwater Beach

10.0 out of 10, Exceptional, (25)
"The location was near the beach, but in a quieter neighborhood. The property was beautiful, clean, and spacious. Property manager was quick with responses to questions and reached out to check on us after we checked in."
Frenchy's Cottage 490 in Clearwater Beach
New Listing Tropical Sunset beach Cottage
Beach nearby

New Listing Tropical Sunset beach Cottage

9.8 out of 10, Exceptional, (17)
"We have stayed in the area for the past 7 plus years ,so far one of our favorites.Met some very nice people while we were staying there .Great location for anyone traveling by foot everything is near by .Hope to get the opportunity to stay again."
New Listing Tropical Sunset beach Cottage
Key West Style Cottage - with pool/hot-tub
Outdoor pool

Key West Style Cottage - with pool/hot-tub

8.6 out of 10, Excellent, (14)
"Close to downtown very lovely looking location "
The price is AED 239
AED 634 total
includes taxes & fees
14 May - 15 May
Key West Style Cottage - with pool/hot-tub
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
Beach nearby, sun loungers, beach towels

100 Steps to the Beach, Family and Pet friendly Real Beach Cottage

9.2 out of 10, Wonderful, (54)
"Awesome location and easy booking."
The price is AED 915
AED 2,550 total
includes taxes & fees
14 May - 15 May
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
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)
"Oceanfront property that felt like also having a private beach."
Your own private Beachfront Home On the Sands of the Gulf. Can't get any closer
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Fridge, microwave, oven, stovetop

White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!

9.8 out of 10, Exceptional, (136)
"Great location, parking, kitchen/dining area, bathrooms, beds, place to watch the game, and decor. Wonderful!"
White beaches, walk to restaurants and shops! Family vacation /Romantic getaway!
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
Terrace/patio

Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool

9.2 out of 10, Wonderful, (22)
"Great place to stay! Exactly as pictured w a cute little pool and right on the beach as well! "
Beach Lodge:2 Story Sleeps up to 12* Beach front pavilion* heated pool
Bright, Clean and Cozy Coastal Cottage in Ozona
Outdoor dining

Bright, Clean and Cozy Coastal Cottage in Ozona

9.8 out of 10, Exceptional, (16)
"We enjoyed our stay at Patrick's place. He is a great host and very responsive to our questions. The house is large and with a nice backyard and a well-stocked kitchen that we loved. Thank you!"
Bright, Clean and Cozy Coastal Cottage in Ozona
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)
"I was very pleased with our room and the pool area was perfect pool was clean and warm. Laundry was so easy too. Good restaurants all around "
Tropical Coquina Cove Studio #5 Heated POOL. 5 Min Walk to Beach
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!
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, (35)
"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
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
8.4 out of 10, Very Good, (4515)
"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, (3211)
"Friendly staff near beach great stay "
The price is AED 724
AED 910 total
includes taxes & fees
27 May - 28 May
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, (605)
"Location was great, close to everything. "
The price is AED 417
AED 471 total
includes taxes & fees
15 May - 16 May
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.