Beachfront holiday rentals in Town &#x27;n&#x27; Country

Lounge chairs are arranged on the sandy beach, accompanied by thatched umbrellas providing shade. The calm waters of the bay are visible in the background, and a multi-story building is situated beyond the beach area.

4.86 out of 5 average rating, 142 reviews

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

A wooden pier extends over smooth waters, bordered by rocky outcrops. The sky is painted in vibrant hues of orange and purple as the sun sets on the horizon, casting a tranquil glow across the scene.

4.76 out of 5 average rating, 285 reviews

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

4.95 out of 5 average rating, 22 reviews

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.

Apartment in Madeira Beach

Waterfront Condo | Gulf Views | Beach Access&Pool

Welcome to beautiful Madeira Beach! Whether you are taking time away from cold weather or planning a staycation getaway, this waterfront condo is the place to relax, unwind, and take in the beautiful water views. Featuring 1 king bedroom 1 bathroom with a queen size sleeper in the living room. Private balcony over looking the water. All new appliances and furniture. Located steps from the community pool, across the street from ROC park, and a 5 minute walk to the beach /local restaurants.

5.0 out of 5 average rating, 16 reviews

Bungalow in Davis Islands

The exterior of the bungalow features a charming blue brick facade, complemented by white trim and shutters. A red electric buggy is parked in the foreground, while cozy yellow chairs are positioned on the porch behind a white railing, surrounded by well-maintained greenery.

Davis Island Bungalow

Experience the charm of island living in this lovely Davis Island Bungalow. It is tastefully furnished and fully equipped. Notable features include wooden floors, tiled details, and cozy carpeted bedrooms. The bungalow boasts new appliances, a screened-in back porch, a jacuzzi, and an electric buggy for relaxing rides around the island. The property also offers a spacious backyard and patio with a BBQ grill. Enjoy convenient access to Busch Gardens, Hyde Park Village, and the River Walk.

4.99 out of 5 average rating, 80 reviews

5.0 out of 5 average rating, 48 reviews

Home in Crystal Beach

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!

Guest suite in Tarpon Springs

Guest Suite + Pool ~ 2 min from the beach

Kick back and relax in this deluxe guest suite, with your own private pool and patio! **Hosts Cover AirBNB Service Fees Now** This spacious ground floor unit features a queen size bed, bathroom, small well-stocked kitchenette, and exclusive access to patio and pool from your unit. Just a 2 min drive to Sunset Beach, 5 min to Fred Howard Park, and 7 min to the Sponge Docks. Also just a short drive to Dunedin & America’s #1 Beach: Clearwater Beach. Enjoy FL livin’ at its finest! ☀️

4.86 out of 5 average rating, 42 reviews

4.86 out of 5 average rating, 29 reviews

Cozy, Remodeled Retreat with Stunning Sunset Views

Paradise awaits on Rocky Point Island! Enjoy gorgeous Florida sunsets from your private balcony and relax in our cozy condo with everything you need for your stay. We're just minutes from Tampa International Airport, the cruise port, and beautiful beaches. Enjoy the heated pool, waterfront views, and delicious food and drinks from the poolside restaurant. Whether you're cruising, exploring Tampa, or simply relaxing, you'll love your stay—and can't wait to come back!

Superhost

Home in Oldsmar

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.

4.91 out of 5 average rating, 77 reviews

4.83 out of 5 average rating, 12 reviews

Home in Crystal Beach

Near Trail & Pier | Crystal Beach Bungalow

Welcome to our 3-bedroom, 2-bath Crystal Beach home — a fully remodeled retreat with bright open spaces and a private backyard gazebo. • Fully updated interior with a modern coastal feel • Bright living area with a smart TV and fast WiFi • Fenced backyard with outdoor dining under the gazebo • About 1 block to the Pinellas Trail and 3 min drive to Crystal Beach Pier Settle in and enjoy an easy Palm Harbor stay with room to relax, cook, and head out on the trail.

Superhost

Apartment in Madeira Beach

Two Full Units. Walk to Beach. Pool. Fishing Dock.

Perfect for larger families or groups traveling together, this beautifully remodeled two-unit ground-floor retreat offers comfort, space, and flexibility in one of Madeira Beach’s most desirable waterfront communities. With two fully renovated condos located side-by-side, you’ll enjoy the convenience of being together while still having plenty of room to spread out and relax.

5.0 out of 5 average rating, 3 reviews