Holiday rentals with a fireplace in Madeira Beach

Centrally Located Cozy 1-bed Private Cottage!

This charming private cottage is ideally located near beautiful views, beaches, art, culture, restaurants, and a variety of family-friendly activities. Guests love the space for its peaceful ambiance, great location, and inviting outdoor areas. It’s a perfect stay for couples, solo travelers, business guests, or anyone looking for a cozy getaway. Enjoy private parking just steps from the entrance, along with a BBQ grill, a brand-new hot tub, and an outdoor gas fireplace—perfect for relaxing!!!

JOJO'S Beachside 1Acre Estate-New Pool

LUXURY CUSTOM HOME WITH NEW HEATED SALTWATER POOL ONLY 1.5 MILES TO BEAUTIFUL WHITE SAND REDINGTON BEACH ON 1 ACRE OF LAND. HOME HAS JUST BEEN TOTALLY RENOVATED WITH TASTEFUL FINISHES. THIS AREA IS VERY QUIET AND UNIQUE FOR PINELLAS COUNTY WITH LARGER LOTS AND HOMES. 2300 SQUARE FEET WITH HIGH VAULTED CEILINGS. LARGE OPEN KITCHEN, T.V.'S IN EVERY RROM. GREAT LOCATION JUST MINUTES FROM: COFFEE SHOPS , GROCERY STORE, SHOPPING, RESTAURANTS, MOVIE THEATERS AND PARKS. LARGE PAVER DECK BY POOL AREA.

Tropical Beachfront Penthouse-Beach Cottages

Beach Cottages II (#2505) Welcome to this spacious top floor oceanfront condo in beautiful Indian Shores, between Clearwater & St Pete Beach on the crystal clear waters of the Gulf of America. This exquisite condo with magnificent oceanfront views is just fabulous! Great care is taken to ensure everything about this vacation home is remarkable & tastefully complimented with King & Queen beds, full kitchen/dining/bar area, Free WiFi, Premium Cable TV, Garage Parking, Private Beach, Pool & Spa.

Gulf View Penthouse | Steps to Beach + Johns Pass

Your Penthouse Paradise awaits at our Gorgeous, 7th-floor Gulf-View Condo in the new Madeira Bay Resort! Enjoy sweeping views of the beach, Gulf of Mexico, & miles of pristine coastline. Just steps from the sand & 1 block from John’s Pass Village & Boardwalk. Walk to dining, shopping, bars, & water sports. Come experience the best of Madeira Beach & make unforgettable memories in our newly furnished, well-stocked, luxury retreat w/all the comforts of home. Perfect for groups or families alike.

Heated Pool no xtra chrge/Hot Tub 0.7 mi to Beach

Welcome to our beach house! - Prime location! 0.7 miles to Indian Shores - Heated pool at no extra charge - Hot tub, saltwater pool, mural for photos and outdoor shower -Family friendly (pack and play, booster seat and kid friendly dishes) - Chef kitchen with double ovens -Beach essentials (beach chairs, wagon, toys and towels) - Quiet and safe neighborhood Beaches: - 2 min to Indian Shores & Redington Beaches - 10 min to Madeira & Indian Rocks - 20 min to Clearwater & St. Pete

The Seascape Premier Beachfront Cottage-Gulf View

Treat yourself, you deserve it! Our condo is updated and furnished for your comfort and convenience. It's the perfect place for a romantic couples getaway, fun in the sun for families or a paradise of peace for seniors. Enjoy watching the boats sail by from our balcony or laying by our pool and basking in the sunshine. Step out to the beach, feel the warm sand between your toes and indulge in the Gulf. Make lifelong memories and melt your stress away at Indian Shores.

Beachfront Penthouse, 6 beds, Walk to Beach Bars

Enjoy this modern beachfront condo in Treasure Island with stunning Gulf views. The main level features a queen bedroom, while upstairs offers a king master suite with a private balcony—perfect for sunset drinks or morning coffee—and a third bedroom with two bunk beds. Beach chairs, umbrella, and toys included. Walk to Caddy's on Sunset Beach, beach bars, and waterfront dining. Construction rates: Pool closed. Brand new w pool expected to open by August 1st 2026!!

SHEEK and Glam- heated pool Updated! 3 mi to beach

UPDATED modern Light and bright colorful condo w FREE HEATED POOL! First floor NO stairs. 2 miles from the beach. Crazy FAST WIFI- at 600mbps !!! Great central location close to 2 malls, restaurants, parks and many local gulf coast beaches. SAFE GATED quiet community has a heated pool, gym, tennis courts and gas grills for you to enjoy. Just bring your beach blanket and swim suit and RELAX! Walking distance to so many stores/restaurants and the Pinellas trail !

Popular Beachside Studio w Relaxing Patio & Palms!

The true gem of Treasure Island! Tucked right off of Gulf Blvd this is one of three stylish studio units nestled in a coconut palm-fringed private courtyard with a residential cottage onsite. This cozy spot overlooking a lush tropical garden is just steps from a white sand beach & walking distance to dozens of laid back beach bars, live music & dining. Please note: There’s no guest parking on-site, but paid parking is nearby as well as a frequent public trolley.

Gulf Front Condo · Beach + Fire Pit + Kayaks

**NEWLY RENOVATED!** Welcome to Tides & Vibes, your personal slice of paradise, accommodating 12 guests! This beachfront retreat, perched directly above the shimmering Gulf with powdery soft sand just steps from your door, offers a spacious and comfortably furnished beachfront balcony inviting you to unwind while soaking in sweeping ocean views, cool breezes, and picture-perfect sunsets. Book your stay and experience the magic of Indian Shores!

Luxury 4BR Beach House on the Sand

Escape to this beautifully remodeled 4-bedroom, 3-bath beach house in Redington Beach with direct beach access and breathtaking ocean views. Perfect for families and groups, this spacious coastal retreat features a pool table, jetted tub, private balconies, outdoor patios, and modern amenities just steps from the sand. Enjoy the ultimate Florida beach vacation near top dining, sunsets, and white sandy beaches in this luxury seaside getaway.

Gulf View Apartment - Steps From The Beach

Wonderful coastal retreat - Gulf view apartment in a block of 2 with 2 good size bedrooms, open plan kitchen, lounge, garage and parking - have fun with the whole family at this stylish modern place. A quiet and private location mid way between the restaurants and bars of John's Pass and Madeira town center and across the street from the beach. Private balcony, secluded patio and garden with BBQ and chairs - Non Smoking Unit