Beachfront vacation rentals in Town 'n' Country

Rocky Point paradise

New queen size bed and 65" HDTV. Centrally located, directly on Tampa Bay. Condo is located 5 minutes to Tampa Airport, International mall, Westshore Mall, Raymond James Stadium. Award winning Clearwater Beach and St. Petersburg Beach 20 minutes. Minutes to downtown Tampa, Ybor City. Yankees training camp. Walking distance to many restaurants. beach volley ball, beach/sunning area, gas firepit ,heated pool, BBQ grills, 24 hr Laundry facility. Balcony overlooks water. check in/check out is 24/7

Beach Front at “The Shore”

Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

262*NEW! 3 beds x 2 bath. Amazing Waterfront Views

This is paradise, in Tampa Bay! All waterfront resort conveniently located at the Sailport, of Rocky Point Island! This updated and spacious condo offers 2 bedrooms and 2 bathrooms with a full kitchen and stunning views of the Bay. The condo comes equipped with amenities such as a heated geo-thermal pool, volleyball court, barbecue, fire pits, lounge areas, as well as a fitness outdoor area. It's prime location for entertaining guests, friends, and family. Your minutes from airports, and beaches

Waterview Balcony Condo & Fireplace | Heated Pool

Welcome to the Flamingo Suite, our renovated Bayview condo with a panoramic view of the water! Sitting on the 3rd floor with a private balcony, the Flamingo 🦩is your perfect romantic getaway or family vacation spot. Quiet, amazing sunset views, dolphin spotting, with in-suite entertainment and even a walk-in shower! You also get to enjoy the resort amenities including a year-round HEATED POOL, bar & grill on the water, convenience store on the 2nd floor, 24/7 security, and FREE parking & wifi!

Sunset Over Tampa Bay-Serene Waterfront Escape

Wake up to breathtaking waterfront views from your private balcony at Sailport Waterfront Suites, located on Rocky Point Island—Tampa’s only true waterfront resort. This beautifully renovated 1-bedroom, 1-bath condo offers direct water views. Inside, you’ll find a modern space thoughtfully designed for a comfortable and memorable stay—ideal for couples, friends, or business travelers. Start your mornings overlooking the water, spend your days exploring Tampa’s top attractions or nearby beaches.

“Beach Walk Retreat • Free Parking

Prepare to be swept off your feet by this stunning 2-bedroom apartment, situated just one block away from the beach. The perfect choice for families and couples alike, this property offers a fantastic opportunity to soak up the sun. Take a 5-minute stroll down to the beach and indulge in a relaxing day of beachcombing, building sand castles or taking a dip in the ocean. Take a break from the sand and head back to your tranquil haven, where you can cook up a delicious meal at the backyard grill

The Harbor Condo Beach Escape!

The Harbor At Town Center is a brand new property in Madeira Beach! Top reasons to Book: • Private and beautifully furnished balcony overlooking the marina! • Steps away from beautiful, white sand Madeira Beach! • Wonderful amenities such as heated pool and spa as well as free Wi-Fi, 2 secured parking spots, and a washer and dryer! • Beautifully decorated throughout to reflect coastal comfort. • The location is great too! Close to a variety of restaurants, entertainment, and unique shopping.

Waterfront Villa w/Hot Tub• Game Room•Kayaks•Bikes

Welcome to Seaside Sanctuary 🌊🌅 – Your Ultimate Waterfront Escape Nestled in charming Crystal Beach, this spacious 4-bedroom, 2.5-bath retreat perfectly blends luxury, comfort, and coastal fun. Go kayaking from your direct Intracoastal access, soak in unobstructed sunsets, relax in the hot tub, challenge friends in the game room, or grill a delicious meal on the patio 🥙. Perfect for family reunions, bestie getaways, wedding weekends—or simply because you deserve a seaside escape!

Villa Madeira

Property Type Condominium Unit Code VM204 Beds 1 king bed, 1 queen bed, 2 twin beds Bathrooms 2 bathrooms Rooms Sleeps 6 Reserved Parking Pets No pets allowed. Living Air Conditioning, Central Air, High Speed Internet, Ironing Board, Linens, Washer & Dryer Business Nearby ATM, Nearby Bank, Nearby Internet Cafe Kitchen Coffee Maker, Cookware, Full Kitchen, Entertainment Cable TV, DVD Outdoor Balcony, Beach, Outdoor Shower, Shared Pool Geographic Close to Town and John's Pass, On Beach

Amazing Private Beach Home

🏡 Welcome to your stunning waterfront retreat with a true million-dollar view! Tucked away on a peaceful cul-de-sac along Oldsmar’s picturesque Shore Boulevard, this elevated home offers a truly special and serene escape. Set on a generous half-acre lot, the property showcases sweeping panoramic views of the sparkling Tampa Bay waters. With 165 feet of private water frontage, you’ll be perfectly positioned to relax, unwind, and enjoy an unforgettable waterfront stay.

Special 8/8-29/2026-All Rooms Direct Beach Front

Special Rates for August 18-29, 2026. All Rooms Directly Beach Front and directly on the Gulf of America. Elevator and heated pool fully operational. You will not believe having all your living area and both bedrooms facing the Gulf of Mexico. You will enjoy watching TV, cooking, wireless Wi-Fi, waking up and going to sleep, seeing the Gulf of Mexico. Remember do not forget to have your favorite drink on the balcony, watching the amazing sunsets.

NEW Sea Drift Oasis - Heated Pool, Spa, Game Room

Welcome to Sea Drift Oasis, an elegant coastal sanctuary just one block from Crystal Beach. This luxury retreat features a heated pool and spa, refined firepit lounge, private game room with pool table and PS5. Steps from a scenic fishing dock and unforgettable sunsets, this 4-bedroom home is ideal for discerning families and golf or fishing groups seeking privacy, comfort, and a premium coastal experience.