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

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.

Amazing Heated & Screen Pool w/ Stunning Design!

🏡Step inside to discover a harmonious blend of comfort and style. The open-concept layout invites you to gather, dine, and relax with loved ones. The home features warm wood cabinetry, stone countertops, modern stainless-steel appliances, and tropical-inspired furnishings that make the space feel both upscale and inviting. Enjoy a resort-style screened pool area, complete with festive string lights, colorful floaties, patio seating, outdoor dining, and a covered tiki-inspired hangout space.

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.

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!

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.

Guest Suite + Pool ~ 2 min from the beach

Kick back and relax in this deluxe guest suite, with your own private pool and patio! 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! ☀️

Mobbly House

A cozy dwelling in the quaint neighborhood of Oldsmar. Golfcart town and 30 minutes from Clearwater Beach and Honeymoon Island state park. Mobbly House is across the street from Mobbly wildlife preserve nature park and beach on Old Tampa Bay with empower zip lines one mile away. Also check out our other listing, Fountain House if available.

Island Retreat w/ Hot Tub, Cold Plunge + Game Room

Escape to Indian Bluff Island in this relaxing Palm Harbor retreat featuring a hot tub, cold plunge, and a fun game room. Take the kids fishing at the marina just down the street, or unwind in your private outdoor spaces after a day at the beach. The perfect mix of island charm, family fun, and coastal comfort.

Breathtaking Waterview Condo!

Welcome to the charming condo in Boca Ciega Resort. Enjoy breathtaking water views, sunsets and even dolphins from your own balcony! Minutes away from the beautiful Madeira Beach, Treasure Island Beach, and many more. Dine and shop at the famous John's Pass and take a walk at Pinellas Trail.