Search Gulfport Cottage Rentals from CA $94

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Check prices for these dates

Next weekend
Aug 29 - Aug 31
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Sep 5 - Sep 7
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Sep 19 - Sep 21
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Oct 17 - Oct 19

Browse Select Gulfport Cottages

Our top choices for Gulfport cottages

Cozy St Pete Home ~ 2 Mi to Madeira Beach!
House (1 Bedroom) | Front of property

Cozy St Pete Home ~ 2 Mi to Madeira Beach!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Spacious for a one bedroom flat. Exceptionally quiet. Would stay there again. A good value. "
The price is CA $122
CA $310 total
includes taxes & fees
Aug 22 - Aug 23
Cozy St Pete Home ~ 2 Mi to Madeira Beach!
The "Grouper"
Beach

The "Grouper"

9.6 out of 10, Exceptional, (31)
"Great location."
The price is CA $137
CA $295 total
includes taxes & fees
Aug 29 - Aug 30
The "Grouper"
Romantic Island Getaway Just Steps from the Beach
TV

Romantic Island Getaway Just Steps from the Beach

2.0 star property
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
The price is CA $229
CA $704 total
includes taxes & fees
Aug 22 - Aug 23
Romantic Island Getaway Just Steps from the Beach
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
Beach nearby, sun loungers, beach towels

Sleeps 6 Daily Rentals, Pets OK, Hot Tub

8.6 out of 10, Excellent, (53)
"Host was very nice & accommodating "
The price is CA $161
CA $459 total
includes taxes & fees
Aug 24 - Aug 25
Sleeps 6 Daily Rentals, Pets OK, Hot Tub
7mi to Anna Maria Newly Renovated Private Cottage
Private kitchen

7mi to Anna Maria Newly Renovated Private Cottage

The price is CA $94
CA $345 total
includes taxes & fees
Aug 29 - Aug 30
7mi to Anna Maria Newly Renovated Private Cottage
Key West Style Cottage - with pool/hot-tub
Property grounds

Key West Style Cottage - with pool/hot-tub

8.8 out of 10, Excellent, (15)
"We really enjoyed our stay and the cottage was very clean and quiet! It is within walking distance of shops and restaurants! We would definitely like to stay here again! The pool area and common area were very nice as well!"
The price is CA $90
CA $239 total
includes taxes & fees
Sep 10 - Sep 11
Key West Style Cottage - with pool/hot-tub
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, (122)
"We LOVED staying at Capt. Al's corner cottage. It was such a cute place and perfect for what we were looking for. Walking distance to everything, steps away from the beach and so relaxing! We especially loved the hot tub that was just out the back door and the atmosphere was so "beachy"....5 stars is not enough for this little gem of a place!"
The price is CA $186
CA $488 total
includes taxes & fees
Aug 22 - Aug 23
Historic Beach Cottage steps from beach. Pet friendly!
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, (57)
"Great location and vibe. Owner Captain Al and housekeeper Nancy were both awesome hosts! They were around when you needed them, but never intrusive. We can't wait to go back! "
The price is CA $211
CA $790 total
includes taxes & fees
Aug 22 - Aug 23
100 Steps to the Beach, Family and Pet friendly Real Beach Cottage
Openings for April and May at our Beach Cottage-3 minutes to the Gulf of Mexico!
Sun loungers, beach towels

Openings for April and May at our Beach Cottage-3 minutes to the Gulf of Mexico!

9.6 out of 10, Exceptional, (5)
"The property was beautiful and beachy! So many small special touches! Wish we had more time, and could have stayed longer! I will definitely be back on my next trip down!"
The price is CA $181
CA $527 total
includes taxes & fees
Aug 25 - Aug 26
Openings for April and May at our Beach Cottage-3 minutes to the Gulf of Mexico!
Family Beach Apartment steps from the beach. Pet Friendly!
Beach nearby, sun loungers, beach towels

Family Beach Apartment steps from the beach. Pet Friendly!

8.8 out of 10, Excellent, (39)
"Was very relaxed, super close to beach and pool. Will stay again"
The price is CA $167
CA $649 total
includes taxes & fees
Aug 24 - Aug 25
Family Beach Apartment steps from the beach. Pet Friendly!
Steps from Beach, Pets OK, Daily Rentals, Historic Beach Cottage
Sun loungers, beach towels

Steps from Beach, Pets OK, Daily Rentals, Historic Beach Cottage

9.2 out of 10, Wonderful, (51)
"We enjoyed our stay. Bed was comfortable, close to everything. Cottage was just as described. Nothing too fancy but good"
The price is CA $197
CA $624 total
includes taxes & fees
Sep 15 - Sep 16
Steps from Beach, Pets OK, Daily Rentals, Historic Beach Cottage
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
Property grounds

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

10.0 out of 10, Exceptional, (24)
"Wonderful place. Host was great. Thanks for having us. "
The price is CA $205
CA $479 total
includes taxes & fees
Aug 24 - Aug 25
Chic Cottage Walk to Downtown Dunedin & Waterfront Pets Ok- Barefoot Parrot 3
Private King Bed Suite-Near AMI Beach-Walk D’Town.
Marina

Private King Bed Suite-Near AMI Beach-Walk D’Town.

9.6 out of 10, Exceptional, (36)
"The Sea Horse Cottage and Bradenton area were charming and beautiful....we had a nice time!!"
Private King Bed Suite-Near AMI Beach-Walk D’Town.
Stay steps from the sand in this charming single-family home. Enjoy exclusive beach access at Sunburst Inn, featured on HGTV. Cozy comfort for up to 4, and an unbeatable location on the Gulf. Perfect for a romantic escape or small family getaway.
On the beach

Stay steps from the sand in this charming single-family home. Enjoy exclusive beach access at Sunburst Inn, featured on HGTV. Cozy comfort for up to 4, and an unbeatable location on the Gulf. Perfect for a romantic escape or small family getaway.

9.8 out of 10, Exceptional, (22)
"Had a great time no complaints"
The price is CA $217
CA $608 total
includes taxes & fees
Aug 25 - Aug 26
Stay steps from the sand in this charming single-family home. Enjoy exclusive beach access at Sunburst Inn, featured on HGTV. Cozy comfort for up to 4, and an unbeatable location on the Gulf. Perfect for a romantic escape or small family getaway.
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, (190)
"Loved this place! Perfect with all the needed amenities. Will definitely stay here again if in the area."
The price is CA $212
CA $420 total
includes taxes & fees
Aug 25 - Aug 26
The Purple Flower - 30 Second walk to the Beach. Free parking.
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Property grounds

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes

10.0 out of 10, Exceptional, (3)
"The property was so well appointed with a cute decor. Everything was clean and well stocked with necessities. Enjoyed our visit, highly recommend!"
The price is CA $293
CA $604 total
includes taxes & fees
Aug 24 - Aug 25
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Beach nearby, sun loungers, beach towels

100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals

9.0 out of 10, Wonderful, (76)
"Cute quiet place Fair price and close to beach and restaurants. Would stay again"
The price is CA $245
CA $841 total
includes taxes & fees
Aug 25 - Aug 26
100 Steps to Beach. Pets Ok, Real Beach House, Daily Rentals
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
Property grounds

Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2

10.0 out of 10, Exceptional, (17)
"We absolutely loved our stay and Jen was very responsive and helpful. We’ll definitely be back."
The price is CA $205
CA $479 total
includes taxes & fees
Aug 24 - Aug 25
Private Yard Walk to Downtown Dunedin & Waterfront Pets Ok - Barefoot Parrot 2
Blushing Flamingo- Triplex with heated pool, across the street from the beach
Pool

Blushing Flamingo- Triplex with heated pool, across the street from the beach

10.0 out of 10, Exceptional, (1)
"We were happy with rental. Everything was clean. The unit was very well stocked with everything. A lot of beach gear. LocaPlenty of parking "
The price is CA $156
CA $415 total
includes taxes & fees
Sep 1 - Sep 2
Blushing Flamingo- Triplex with heated pool, across the street from the beach
Beautiful Condo on Pine Ave, 2 Blocks to Beach
A heated pool

Beautiful Condo on Pine Ave, 2 Blocks to Beach

8.8 out of 10, Excellent, (23)
"Great location, very comfortable property! We loved the 2 covered porch areas at the front and back of the unit. We had a little trouble with the AC but the owner was very responsive. We would certainly rent this unit again!"
The price is CA $276
CA $942 total
includes taxes & fees
Aug 25 - Aug 26
Beautiful Condo on Pine Ave, 2 Blocks to Beach
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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Top Gulfport Hotel Reviews

Hyatt Regency Clearwater Beach Resort & Spa

Hyatt Regency Clearwater Beach Resort & Spa

10/10 Excellent
"The view from our room was amazing and it was so nice to be right on the beach! The resort had great accommodations; we especially loved spending time in the pool area."
Chelsea L 7-night trip
Posted 18 hours ago
Hyatt Regency Clearwater Beach Resort & Spa