Beach house holiday rentals in Honeymoon Island

Beach front cottage on Treasure Island, FL

Beautiful brand new cottage located directly on the Gulf of Mexico. Quiet and quaint, old style cottage that has miles of beach to walk and enjoy. The cottage is newly built, and includes state of the art bathroom and kitchenette. The kitchen includes fridge with ice maker, microwave, airfryer, induction cooktop, and fully equipped. The cottage is within walking distance to grocery store, trolley transit, dining, and is only 15-20 minutes to downtown St. Pete. Mainly weekly or monthly rentals.

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.

4 Bedroom, 3 Bathroom House 1 Block From The Beach

WALK ONE BLOCK TO THE BEACH! You read that right, just one block (1 minute walk) to the most prestigous beach in America. This piece of paradise is unreal. The home features TWO Master Suites, one with a wet bar! There are two other generous size bedrooms, 3 full bathrooms, an open floor plan, a beautiful patio, completely updated, and so much more. The north end, where this home is located, has an extremely private beach area. Enjoy it as a couple, bring some friends, or the whole family!

Oceanfront Boho Bungalow Breeze

Step into the soul of Indian Rocks Beach with this newly restored stone beach cottage, offering direct access to the sand that blends nostalgic charm with modern luxury. This coastal gem is one of IRB’s original stone cottages, lovingly updated while preserving its unique architectural character. Inside, you’ll find a boho-inspired interior with all the modern conveniences. Walk barefoot from your door to the shore. This is not your average rental—it’s an authentic luxurious experience.

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!

Luxe Beach House A/Heated Pool/2 min walk to beach

Welcome to your home away from home. Sand, sun and ocean breeze are waiting for you. BeachHouse is located 2 minutes walk from the beautiful and quite beach with direct beach access.Its a newly built four story house with nice and private backyard,heated pool,hot tub and beautiful rooftop. We have everything that you need for bigger groups of families to relax on your Beach vacation. BeachHouse is in a quiet neighborhood and walking distance from restaurants, bars and stores. BTR#2099

Lux Madeira Beachfront Home

Wake up to sweeping Gulf views in this rare 4BR/sleeps 10 Gulf-front home on Madeira Beach — direct sand access from your door. Spread across multiple levels of living with panoramic water views and private balconies. Designed for relaxed beach living with patio & outdoor BBQ area, perfect for sunset dining. Beach chairs, umbrella & gear included. Minutes from John's Pass. High-speed WiFi & parking included. Private, spacious & truly Gulf-front — Madeira Beach at its finest.

High-end Beach heaven, Sleeps 10, 3 private decks

Ideal for those who appreciate single-level living. 3 bedrooms & 2 baths located on the main floor, & loft-style 4th bedroom upstairs. Enjoy 3 decks!: a private beach deck just a 30-second walk away + front & upper decks offering partial ocean views perfect for morning coffee or for cocktails. The primary booking guest must be at least 27 years old, stay on-site during the reservation, and provide valid government-issued ID to host within 24 hrs of booking. Vtr -1609

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.

Pool • Ocean View • Walk to Beach & Restaurants

- Wake up to ocean views from every room. - This Balinese-inspired coastal retreat blends modern luxury with tropical serenity. This fully renovated 2-bedroom, 1-bath oceanview retreat was thoughtfully designed to feel like a private Balinese escape on the water. Every single room features ocean views — from the bedrooms to the living area and kitchen. Natural textures, warm wood tones, and curated décor, create an elevated atmosphere the moment you walk

Luxe 4BR w/ Pool & Hot Tub- Mini Golf

Welcome to Ocean Rise by Ren’s Retreats—your private Florida family retreat designed for comfort, connection, and effortless coastal living. • 5 mins to Indian Shores Beach • 5–15 mins to Redington Shores, Indian Rocks & Madeira Beach • Minutes to parks, trails, dining & shops Unwind after sun-soaked beach days with space to gather, relax, and feel right at home. Please note: The primary guest must be 21+ and present for the full reservation.

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.