Cottage holiday rentals in Pinellas County

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

Ground-floor, direct beachfront 1BR | on the Gulf

This rare ground-floor, direct beachfront one-bedroom sits right on the Gulf of Mexico with unobstructed water views and effortless beach access Step out the door and into a life where the Gulf of Mexico is your backyard — no elevator, no lobby, just you, the sand, and thirty seconds between your pillow and the water. Enjoy your private beachfront patio, a cozy recently remodeled interior, and your own stretch of sand with lounge chairs, umbrellas and front row views right outside your door.

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.

10% Off May Dates | Modern Beach House Stay Now.

Sandy Toes Cottage is a fully renovated beach home just 2 minutes from Indian Rocks Beach. Enjoy modern furnishings, a bright kitchen, spa-style bath, free Wi-Fi, and a backyard with fire pit and hammock. Walk to local dining and shops—your perfect coastal getaway! **NEW AIRBNB PRICING UPDATE** Starting mid-October 2025, Airbnb will show all-in pricing—including an increase fee of 15.5% Airbnb service fee (charged directly by Airbnb to me the host), cleaning fees, and pet fees if applicable!

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 ..

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.

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 prime location. Walk to restaurants, breweries, shops, and live music. Walk to gorgeous 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.

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.

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.

Private Peaceful Cottage-St Pete, Beaches & Trail!

Welcome to our bright coastal cottage — a peaceful retreat just 4 miles from the beach. Enjoy a newly remodeled kitchen and bathroom, two convenient parking spots, folding twin cot, and a couch for extra guests. Located in a quiet neighborhood with plenty of Florida charm and Florida birds. Guests must be 25+, sorry no parties or unregistered visitors. Additional guests $10 per night. ID required within 24 hours. No smoking or vaping anywhere on the property — $500 fee applies.

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

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.