Cottage holiday rentals in Pinellas County

Find and book unique cottages on Airbnb

Top-rated cottage rentals in Pinellas County

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

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Guest favourite

Cottage

4.9 out of 5 average rating, 273 reviews

Vintage Florida Beach Cottage B

Just a short walk to the beach makes this a great beach getaway for couples or families. On your way you can stop at the Cooky Coconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2019, this unit is in updated, very clean and worry free condition. This cottage is located in a quiet residential neighborhood and a great place to relax. Common laundry on shared screened porch. Dogs allowed (extra $45 cleaning). Easy refund policy. Level 2 EV charger

Guest favourite

Cottage

4.96 out of 5 average rating, 130 reviews

Pass-a-Grille Historic Cottage Unit 2

PASS-A-GRILLE HISTORIC COTTAGE UNIT 2 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 2 - 2 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 and back patio area w/ BBQ grill. Private parking for 2 vehicles.

Guest favourite

Cottage

4.84 out of 5 average rating, 127 reviews

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Guest favourite

Cottage

4.96 out of 5 average rating, 203 reviews

Adorable Dog-Friendly Cottage in Quaint Dunedin

Discover a charming 1920's cottage nestled in the heart of Dunedin, 3 blocks from the water and downtown. This delightful cottage is ideally located 2 blks from the Pinellas Trail, the Fenway Hotel, and the Blue Jay's stadium. Surrounded by lush greenery, the cottage boasts a private outdoor space perfect for you to enjoy your coffee. Inside, you'll find a sunny kitchen, a spacious living and dining area, and comfortable beds to ensure a wonderful stay. Come and enjoy a memorable stay here!

Guest favourite

Cottage

4.99 out of 5 average rating, 153 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.

Guest favourite

Cottage

4.97 out of 5 average rating, 292 reviews

Walk Downtown and Waterfront Barefoot Parrot 3

Treat yourself to modern coastal luxury in this spacious upstairs cottage with charming treetop views. Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to Honeymoon Island, Caladesi Island, and Clearwater Beach. Stroll to restaurants, shops, breweries, and breathtaking sunsets, then retreat to your peaceful space. Featuring 2 king beds, a sleeper sectional, and pet-friendly amenities, this bright and coastal getaway is perfect. Book your sunshine escape today!

Guest favourite

Cottage

4.95 out of 5 average rating, 262 reviews

Gulfport Cottage STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

Guest favourite

Cottage

4.79 out of 5 average rating, 117 reviews

Serene French Country Cottage near everything

Unwind in this rustic French provençal, Extra Cosy Cottage w/ Unique Decor in Charming, Artsy Dunedin. Fenced in yard. Free Parking&Wifi. CENTRAL LOCATION Close to Clearwater Beach, Honeymoon Island. Short walk to Downtown Dunedin, Pinellas Trail, Blue Jay Stadium & Beautiful sunsets! Perfect location for Walkers, Runners and Bikers! A home away from home in a very convenient location for quality shopping, dining, nature explorations and beaches! A short walk or Uber away from everything!

Guest favourite

Cottage

4.96 out of 5 average rating, 134 reviews

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.

Superhost

Cottage

4.84 out of 5 average rating, 102 reviews

Palm Cottage * King Bed * Tropical Yard

Located in the heart of historic downtown Tarpon Springs, Palm Cottage (520 sf) is walking distance to the world famous SPONGE DOCKS, and located just blocks away from breweries, restaurants, and the PINELLAS TRAIL. And the BEACH is only 3 mi away! The cottage offers king and twin beds, Wi-Fi, Fire TV, kitchen w/ full stove and fridge, coffee maker, toaster, pots, pans, table, and shared use of the tropical back yard of our 121-year-old Victorian home. 1st time Airbnb guests welcome!

Guest favourite

Cottage

4.88 out of 5 average rating, 110 reviews

Mermaid Cottage

Located in a three unit 'Olde Florida Style Complex' and just 45 steps to Clearwater Beach! The Mermaid Cottage is located on the 1st floor at the back of the complex. This Florida style unit is adorned wood floors and charming island decor. Open to an outdoor patio with furniture. The cottage has two bedrooms, two full baths and an outdoor shower! Living room has a queen pull-out bed. The patio area is completely fenced for private use. Nice, park like charcoal grill.

Superhost

Cottage

4.75 out of 5 average rating, 309 reviews

Below -Deck Studio Gulf Side 40 steps to the beach

An original beach cottage built in 1947. Only 40 steps to the Shores of Redington beach Florida. One free parking spot on premises in front of cottage-far left Pay public parking across from cottage. Seabreeze and wahoo restaurants on the bay 40 steps to the intercoastal is called the Narrows want to rent a kayak and paddle around the bay or take it 40 steps west put it in the Gulf of Mexico. surf shop to rent bikes or Kenny’s corner diner, frog pond broke n board foods