Holiday rentals with a pool in Redington Beach

Pearl of the Sea, 1 BDRM, 2 min walk to the beach

Please note, the gym, jacuzzi, and hot tub are temporarily closed(hurricane damage) Completely remodeled, beach theme decorated, a beautifully furnished second-floor condo just steps away from the white silky sandy beach! Ideal for romantic vacations, honeymoon escapes, and getaways! Located in Madeira Beach Yacht Club, a private gated community, free parking, high-speed WI-FI, TV cable, Netflix, 2 outdoor heated swimming pools, and fishing piers. Please, book at least 7 days before your arrival

Tropical Beachfront Penthouse-Beach Cottages

Welcome to this spacious top floor oceanfront condo at the Beach Cottages 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 size beds, full kitchen/dining/bar area, Free High WiFi, Premium TV, Garage Parking, Private Beach, Pool & Spa.

Coastal Retreat Madeira Beach/John’s Pass Pool

$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Step into coastal style at this Madeira Beach condo with Gulf views. Designed with a beach-inspired theme, this retreat offers a breezy open layout, fully equipped kitchen, and balcony perfect for soaking in sunsets. With resort-style amenities on site and dining, shopping, and entertainment nearby, it’s an ideal escape that blends a laid-back coastal vibe with the convenience of a prime location.

Beautiful Studio on the paradise white sand beach!

The studio at Royal Orleans is a perfect holiday accommodation across from the lovely Redington Beach. The studio offers a sitting area and a kitchen complete with a dishwasher and a refrigerator. A flat-screen TV with cable channels is provided. There is a private bathroom with a bathtub shower. The bed is queen size. The apartment complex has a lovely outdoor swimming pool with a lounge area. Redington Beach is a great choice for travelers interested in sunbathing, swimming and relaxing.

Surf’s UP! Pool, Cabana & Poolside bungalow!

Welcome to the CUTEST mini-resort you’ll want to definitely experience! Step inside and you'll be wowed by the tastefully decorated California-style beach decor that exudes VACATION!🌴 This delightful home comfortably sleeps up to 8 guests, including the cozy poolside PINK bungalow! As cute as the home is, prepare to feel like you’ve entered another world once you step outside. Tropical backyard with optional heated pool +a resort-like tiki cabana will throw you in ultimate vacation mode.

Gulf view Condo with pool in Clearwater/St. Pete

Located between Clearwater Beach & St. Pete Beach, this fully furnished Studio features a full kitchen with a full-sized stainless steel refrigerator and dishwasher, granite countertop, microwave, kitchenware, a Queen bed, a queen size sleeper sofa, closet space, and new AC. This quaint 35-unit resort condo offers a heated pool with tables, lounge chairs and gas grill within a smoke-free tropical courtyard. Just step out the front door for a view of the gulf & 3 mins. walk to the beach.

Florida Island Beauty@theBeach@Heated Pool

My place is close to white sand beaches and has a heated pool. Price is amazing and its fully renovated in the latest fashion with fun beachy accents! You’ll love my place because of the location, the neighborhood, and the outdoors space. My place is good for couples, solo adventurers, a parent and a child. I have adjusted my prices so they are adjusted accordingly with consideration of the area recovering from hurricane Helene from last year. Photos were taken on August 25th, 2025.

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.

🏝🏝Charming Bayfront Condo at Boca Ciega

This lovely waterfront condo located in wonderful Boca Ciega Resort in St. Petersburg, FL has everything you need for an extended stay. Centrally located with great views and amenities. Enjoy the sunset and gorgeous views whether it’s inside while lounging on the sofa or outside on the balcony. It sleeps up to 3 people (one bedroom and a sofa in the living room). Full kitchen, TV in living/bedroom, WiFi, and close proximity to the best beaches Florida has to offer.

~Shore Thing~ Coastal Exquisite Waterfront Condo

🏖️ Shore Thing Condo 🏖️ 🌅 Sunset Serenity — Relax as the sun melts into the horizon. 🚶Beachside Bliss — Just steps from powdery sands and shimmering Treasure Island waters. 🐬 Marine Magic — Spot dolphins dancing and manatees gliding by. ✨ Stylish Coastal Vibes — Modern interiors with breezy beach flair. 🍽️ Chef’s Dream — Cook with ease in a luxury kitchen. 👩‍💼 Service with Heart — Your comfort always comes first

Royal Orleans at Redington Beach ( Studio 203 )

Royal Orleans 203 is a studio condo with one queen size bed that sleeps up to 2 . The condo is located on the second floor overlooking the (heated) pool . A super relaxing Gulf shore vacation that puts you just across from the beach, restaurants, and shops. In addition to the beautiful pool at Royal Orleans , you are close to golf and boating opportunities. It’s a recipe for a wonderful vacation in Redington Beach, Florida.

Penthouse,intercoastal, 3/3 views/heated pool

This stylish place to stay is perfect for group trips. Brand New Luxury Madeira Beach Penthouse With Heated Pool 4 floors up with partial beach and intercoastal views, all on a level floor plan 4 stories up with elevator access! Enjoy the comforts of new unit with modern appliances and fixtures in this 3/3 that bolsters a king master bedroom, two guest queen bedrooms all with in suite full bathrooms.