
Cottage vacation rentals in Clearwater
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Top-rated cottage rentals in Clearwater
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Walk to beach shops food drinks “The Cottage”
Island Rum Suites has another cozy little cottage on the list of awesome places to stay near Indian Rocks Beach only 1/2 mile away! Location is everything and this is it! 25 miles from TIA, and all major attractions in Tampa. You will be in walking distance to the beach (IRB), beautiful sunsets, nature parks, nature trails, bike trails, marina, boat launch, shopping, sports bars, restaurants, pizza and ice cream! There is even a water park less than 1/2 mile away! fall special stay 4 get 1 free

Pass-a-Grille Historic Cottage Unit 1
PASS-A-GRILLE HISTORIC COTTAGE UNIT 1 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 1 - 1 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front patio area w/ BBQ grill. Private parking for 1vehicle on premises.

Walk to Downtown and Waterfront - Private Yard
Steps to Main Street and minutes to beaches, yet tucked away on a quaint street. Private yard with grill in a 100 % prime location. Walk to restaurants, breweries, shops, and live music. Walk to stunning sunsets or drive minutes to award-winning beaches such as Honeymoon Island, Caladesi Island & Clearwater Beach. Designer decor. Sleeps 6. Two king bed suites and a luxury couch that sleeps 2 more. Fully loaded for kids, pets and beach days. Treat yourself and book this Dunedin favorite today.

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.

Florida Guest House
Seminole Oaks House...Beautifully appointed new construction 2-story Guesthouse located in a very quiet setting 10 minutes from Indian Rocks Beach. Walking/biking distance from Walsingham Park and Lake and the Pinellas Trail. Enjoy your morning coffee or evening glass of wine on the balcony..or tree shaded rear Patio w/BBQ grill..Great location for exploring all Pinellas has to offer including the Beaches, Downtown St. Pete,and open air Markets..dedicated parking..very peaceful and private ..

Walkable, fun, local Dunedin experience
Stay in this charming 1920s cottage, where you can walk to local restaurants, breweries, and shops, or take a short walk to the marina for a sunset. Perfectly located in the heart of Dunedin, this home makes it easy to explore the area on foot. Spend your days enjoying nearby beaches, biking the Pinellas Trail, or catching a game at TD Ballpark to watch the Toronto Blue Jays. After a day of beach fun, baseball, or exploring, then enjoy an easy walk for dinner, drinks, or live music downtown.

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.

Luxury Beach Bungalow | Walk to Dining & Sunset
Escape to paradise at Sunshine Escapes IRB! Welcome to Mango, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem radiating a whimsical, small-town charm that evokes nostalgic memories of carefree childhood summers by the shore. Just ✌🏽 blocks away, the Gulf of Mexico beckons, offering pristine fluffy sand and unforgettable sunsets. As the sister cottage of Coco, Mango invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect beach getaway awaits!

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.

Cozy Cottage for Lovers
Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.

Adorable Villa 1 min to Downtown Dunedin
Welcome to our 1/1 cottage-style villa, which is minutes from Downtown Dunedin. Only a short walk to Main Street and a 12 min drive to Honeymoon/Caladesi Island! Walk to the Pinellas Trail, breweries, eateries, waterfront marina, and Blue Jay baseball stadium. Enjoy award-winning cuisine, live entertainment, and breathtaking sunsets before returning to the peace and quiet of your own private area. Dunedin is a gulf cart friend city with local rental available to cruise around town.

B - BEACH HOUSE 3 MIN WALK TO THE BEACH
3 MIN WALK TO THE BEACH. beach cottage, 2 br, 1 bath, well equipped kitchen, Beautyrest beds, very clean. all included, 4 beach chairs, a cooler, beach toys, 18 towels: 4 beach, 4 shower, 4 hand, 4 face cloths, 2 kitchen towels, no stairs, parking up frond for 4 cars, outdoor sitting+ dining, charcoal grill, private laundry room free, high speed Internet 200 megabytes, cable TV, Wi-Fi, short walk to baseball /pickleball/ tennis/ basketball/ skateboard field, no steps.
Popular amenities for Clearwater cottage rentals
Cottage rentals with free parking

"Sweet Harbor Cottage" Walk to Downtown

NEW! 2BR/2BA Finest Vacation Home Steps to Beach

Water Front Super Chic 2BD/ 1 bath - Cottage Wi-Fi

New Beach Retreat | Hammock, PacMan, Walk 2 Beach.

Private Peaceful Cottage-St Pete, Beaches & Trail!

Safety Harbor Cottage

Trendy Seminole Heights Flamingo's

Gulfport Art District - One Block From Beach!
Cottage rentals with a pool

Coral Cottage pool/firepit 3 bed 2 bth sleeps 6

Seaside Retreat Cottages #4

Yachtsman Beachfront Cottage w/ Heated Pool

Family Friendly Beach Cottage in Madeira Beach, FL

Mermaid Cottage

Downtown Cottage | Walk Everywhere, Park once

6B Newly Renovated Casita at Coastal Cottages!

Seaside Cottage- Gulf Waterfront with heated pool
Family-friendly cottage rentals

Cottage by the Coast 2 bd - Pet Friendly

Wow! Coastal Home+ 10 Mins to Dunedin & Beach

Mermaid BeachCottage 3gulfside (30 steps to beach)

Stay in Downtown Dunedin • Walk Everywhere

Tranquil Guesthouse Hideaway (Near MacDill AFB)

Coral Sands I -2/2 Porch, Pool Tbl, Best Location!

2BR Charming Beach House Steps To The Beach 2nd FL

Coveted Sunset Beach Rental: Beautiful 2 Bdrm
When is the best time to visit Clearwater?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ610 | ﺩ.ﺇ679 | ﺩ.ﺇ760 | ﺩ.ﺇ606 | ﺩ.ﺇ514 | ﺩ.ﺇ518 | ﺩ.ﺇ514 | ﺩ.ﺇ496 | ﺩ.ﺇ452 | ﺩ.ﺇ488 | ﺩ.ﺇ514 | ﺩ.ﺇ547 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Quick stats about cottage rentals in Clearwater

Total vacation rentals
Explore 60 vacation rentals in Clearwater

Nightly prices starting at
Clearwater vacation rentals start at ﺩ.ﺇ220 per night before taxes and fees

Verified guest reviews
Over 6,420 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
50 properties have a dedicated workspace

Wi-Fi availability
60 of Clearwater vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Clearwater rentals

4.9 Average rating
Clearwater stays are highly rated by guests—averaging 4.9 out of 5!

Nearby attractions
Clearwater's top spots, include Clearwater Marine Aquarium, Pier 60, and Countryside 12
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- Anna Maria Island
- Raymond James Stadium
- Busch Gardens Tampa Bay
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