Cottage vacation rentals in Clearwater

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Clearwater

Guests agree: these cottages are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favourite

Cottage in Tampa

4.99 out of 5 average rating, 144 reviews

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, smart TV’s, blackout curtains,shampoo/conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Pet fee $50. Elope/Proposal packages IG lakepossibility

Aug. 3 – 10

$297 CAD per night

Guest favourite

Cottage in Gulfport

4.96 out of 5 average rating, 135 reviews

The Pelicans Roost / Gulfport

The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!

Aug. 9 – 16

$213 CAD per night

Guest favourite

Cottage in Clearwater

4.84 out of 5 average rating, 118 reviews

Beach Guest Cottage. Gulf Semi Private Area.

Come enjoy the Sun & Beach in little Design Beach Guest COTTAGE for 1-2 Persons in quiet green golf area, own entrance & bathroom, in lovely backyard, under 2 oaks. 2 mn to SEA by car, 7 mn to FAMOUS CLEARWATER BEACH. GOOD WIFI, ideal for remote work, self check-in from 3pm to late+ A reading/café corner/armchairs, kettle & complimentary coffee, organic teas and snacks, water in a fridge. No kitchen or tv. Near downtown Clearwater. FREE PARKING on street. Good neighborhood safe & friendly.

Dec. 9 – 16

$187 CAD per night

Guest favourite

Cottage in Indian Rocks Beach

4.99 out of 5 average rating, 155 reviews

Cottage w/ Private Patio | 3 Min Walk to the Beach

Escape to paradise @sunshineescapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach (IRB). This hidden gem radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. Just two blocks away, the Gulf of Mexico beckons, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

Nov. 9 – 16

$338 CAD per night

Guest favourite

Cottage in Palm Harbor

4.78 out of 5 average rating, 167 reviews

Crystal Beach Cottage #1

Original MCM bungalow located 1 blk from the Crystal Beach park. This property has original windows, AC window units, renovated bath and kitchen and every six month upgraded soft goods. It is appointed with all the travelers' needs for a quick get-away or a vacation. Located in a quaint neighborhood setting conveniently located by the Pinellas trail so cyclist, runners & walkers have immediate access. Close to local towns near by & Palm Harbor's Restaurant/bars, & 10 min all the best beaches.

Jun. 18 – 25

$148 CAD per night

Guest favourite

Cottage in Tarpon Springs

4.99 out of 5 average rating, 137 reviews

Cooper Cottage: Cozy, Convenient and Comfortable

Cooper Cottage is for cyclists, boaters, beach goers or those who just want to relax! The Cottage is the front half of a duplex in downtown Tarpon with all the amenities including bikes and beach gear! Walk/bike to Restaurants, Churches, Museums and Parks in under 12 minutes or drive to Fred Howard Beach or Sunset Beach in 7 minutes! Due to allergies of visiting family & friends we do NOT ALLOW PETS OR COMPANION ANIMALS, so you can rest assured that animal allergens will NOT be an issue.

Apr. 26 – May 3

$255 CAD per night

Guest favourite

Cottage in Madeira Beach

4.91 out of 5 average rating, 113 reviews

Flipper's @ Mad Beach Cottage

Flipper's at Mad beach is a few steps away from the sugary sands of Madeira Beach, and close by the famous John's Pass Village & Boardwark where shopping and entertainment is always great. Completely renovated with light porcelain tile, nice furniture, queen bed with memory Thempur-Pedic mattress, exquisite modern shower, tall kitchen cabinets with plenty of storage. Huge private paved fenced backyard with gazebo, great for entertainment and outdoor grilling. You will love the beach decor.

Nov. 3 – 10

$232 CAD per night

Guest favourite

Cottage in Indian Shores

4.95 out of 5 average rating, 110 reviews

OPEN! Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Nov. 14 – 21

$701 CAD per night

Guest favourite

Cottage in Indian Rocks Beach

4.93 out of 5 average rating, 179 reviews

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

Nov. 4 – 11

$284 CAD per night

Guest favourite

Cottage in Largo

4.94 out of 5 average rating, 124 reviews

Fall special 3rd night free! “The Sweet”

Cozy, romantic, 1 king bed, super cute and super sweet! Just a short walk to beautiful Indian Rocks Beach, nature parks with trails, shopping, orange grove, and many restaurants and fun beach bars! Guests have private entrance, full bath, laundry facilities, large back yard with fire pit, bbq grill, beach chairs and cooler. With each stay guests receive a mini super rummy Island Rum Cake and a gift certificate PJ's Oyster Bar! **Fall Special stay 2 nights get 1 free**

Aug. 10 – 17

$218 CAD per night

Guest favourite

Cottage in Dunedin

4.97 out of 5 average rating, 264 reviews

Walk to Downtown & Waterfront- Barefoot Parrot 3

Treat yourself to modern coastal luxury in this spacious & beautiful upstairs cottage w/ lovely treetop views. Steps to Main Street, a short walk to the waterfront & easy drive to Honeymoon/Caladesi Island & Clearwater Beach. Stroll to waterfront, restaurants, shops, breweries, & Pinellas Exercise Trail. Enjoy award-winning dining, live music, & stunning sunsets then take the short walk back to the quiet of your own private space. Fully equipped kitchen. Pet friendly.

Aug. 23 – 30

$350 CAD per night

Guest favourite

Cottage in Indian Rocks Beach

4.96 out of 5 average rating, 293 reviews

Private Heated pool/spa home!

Pool heat available. Swim all year! FIVE STAR CLEAN. WIFI GAME STRONG. WORK REMOTE, KEEP KIDS BUSY, BREATHE CLEAN SALT AIR. BTR#1735 Come explore our gorgeous, resilient Gulf Coast:) Beach bungalow with all of the amenities. Have the house and pool with private oasis all to yourself. Just step out the front door and walk 7 homes to the sandy shores of Indian Rocks Beach. See hundreds of reviews to learn more about us, our place, our style.

Aug. 22 – 29

$697 CAD per night