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.

Location · Beach · Sleep quality

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.

Family · Location · Hospitality

Elevator | Heated Pool & Hot Tub | Pool Table

Welcome to our IRB beach retreat, just a short stroll to the pristine white sands and calm Gulf waters of Indian Rocks Beach! Unwind on the spacious outdoor patio, splash around in the heated pool, relax in the hot tub, or fire up the grill. This beautifully updated beach house offers bright, open living spaces perfect for families or groups seeking a relaxing getaway. Your serene white sand beach escape awaits – no crowded tourist spots here, just pure beach bliss! PETS MUST BE APPROVED

Location · Family · Decor

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!

Location · Value · Kitchen

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

Location · Family · Walkability

Indian Rocks Beach West Side Bungalow

Relax and enjoy the laid-back charm of Indian Rocks Beach from this comfortable coastal retreat. Just a short walk to the beach, it’s the perfect spot for sun, sand, and Gulf sunsets. After a day at the shore, unwind at the property with a private putting green, fire up the BBQ grill for outdoor dining, or hop on the included bikes to explore the neighborhood, local cafés, and waterfront restaurants. Perfect for couples, families, or friends looking for a relaxing beach getaway.

Location · Family · Hospitality

Hudson Waterfront Home "The Surf Shack"

We're not just a place to sleep at night; we're full of fun things to do! We are pool tables, foosball, board games, corn hole, and get togethers outside under the pergola. Use the dock to fish or spot wildlife or to simply relax. Our home is walking distance to Hudson Beach and Robert J. Strickland Park boat ramp! Ollie's on the Beach is 0.4 miles away and Sam's Beach Bar is 0.6 miles. We foresee lots of great sunsets in your future. Allow us to make your stay one of the best!

Location · Kitchen · Getting around

Quiet Escape | Pool, Theater, Game Room & Hot Tub

This spacious 5-bedroom, 3-bath retreat in peaceful Seminole—just one exit from the Gulf Coast beaches—was created for comfort, relaxation, and fun. Ideal for families, groups, or multi-generational stays, it offers the perfect balance of a tranquil getaway with quick access to sunshine, sandy shores, and coastal adventures. Spend your days relaxing by the private pool, soaking in the hot tub, or making the most of the home’s entertainment features while enjoying time together.

Location · Value · Checkout

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

Location · Value · 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.

Location · Comfort · Check-in

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

Location · Family · View

Beautiful New Home with Ocean View, Steps to Beach

Luxurious 3BR/3BA fully furnished new home that sleeps 11. Enjoy the gorgeous ocean views with two large balconies, perfectly located across the street from the beach, Caddy's restaurant and walking distance to several diverse options, and a 15-min walk to John's Pass (jet skis, fishing, restaurants, and more!) Amenities: - Smart TVs in all rooms - Fully equipped Kitchen - Gas grill - Beach accessories - Board Games - Family friendly

Value · Family · Check-in