Holiday rentals in Honeymoon Island
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Top-rated holiday rentals in Honeymoon Island
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Tiki Hut Cottage
This unit private vacation rental is located on the property, plenty of space for 5 quest, 2 bedroom, upper bedroom has a half bath, toilet and sink, lower bedroom has a walk in shower with stack washer and dryer. Conveniently located to the downtown & beach. This unit is pet friendly, we allow 1 dog. Wether your dog is or is not a service dog we have the following guidelines no excessive parking clean up after your pet any physicial damage caused by the pet will be subject to reimbursement
4.96 out of 5 average rating, 204 reviews
Reel Retreat | Lakefront Home with Hot Tub
Reel Retreat is a stylish mid-century lakefront escape on Lake Tarpon, perfect for a relaxing getaway. This spacious 3-bedroom, 2-bath home features an open layout, game area, and thoughtfully designed spaces. Take in breathtaking lake views, unwind on the wraparound deck, soak in the hot tub, or gather by the fire pit. With a hammock, grill, and dock access, it’s the perfect spot for peaceful mornings and stunning sunsets. 2 kayaks on property for the lake.Come stay with us for a reel retreat!
5.0 out of 5 average rating, 31 reviews
Walk Downtown and to Waterfront, Mins to Beaches
Just steps to Main Street Dunedin and minutes to Honeymoon Island and Clearwater Beach, this stylish upstairs 2-bedroom cottage blends modern coastal design with exceptional comfort. Tropical murals, treetop views, two king beds, and a sleeper sectional create a chic and comfortable stay. Fully stocked. Walk to dining, shops, breweries, and Dunedin’s stunning waterfront sunsets, then drive minutes to the beaches. Pet-friendly. Every detail beautifully done—reserve the Barefoot Parrot today.
4.97 out of 5 average rating, 392 reviews
Luxe Private Waterfront Getaway with Pool in Ozona
Awesome single family inter-coastal waterfront home with boat dock and pool. 1800 square feet of luxury, 3 bedroom, 2 bathroom, sleeps 10 people in beds. Master bedroom overlooking the water and pool with king bed. Second bedroom with 1 queen bed. Third bedroom with 1 queen bed. Living-room has 2 queen pull out beds and a large glass door wall that opens up to the spacious screen enclosed pool patio. Full kitchen, dining room, living room, laundry area with washer/dryer. Dock has deep water.
4.93 out of 5 average rating, 107 reviews
The Nest Romantic Boutique style getaway
Where 'Key West meets French Quarter', the Nest Boutique at BananaBay is an invitation to the charm of old Florida, making it easy to plan your visit. Enjoy a cozy restful night in a Tommy Bahama style King bed. Whether it's restaurants and micro breweries, biking and walking trails, beaches and sunsets, your explorations begin right here. Bikes included! You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night.
4.99 out of 5 average rating, 92 reviews
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!
5.0 out of 5 average rating, 49 reviews
Walk Downtown & Waterfront | Dunedin's Best Street
Stay somewhere extra special in Downtown Dunedin — Pickets Cottage. Set on what is widely considered one of Dunedin’s most beautiful and desirable streets, the cottage is just one block from downtown and less than a five-minute walk to the waterfront. Enjoy the best of both worlds: a charming, quiet storybook neighborhood setting behind a classic white picket fence, with Main Street’s restaurants, breweries, shops, festivals, nightlife and the Pinellas Trail just a short stroll.
4.95 out of 5 average rating, 22 reviews
Serenity Bungalow Downtown
Kick back and relax in this stylish bungalow, perfectly situated at the gateway to downtown Dunedin’s vibrant corridor. Explore a variety of shops, microbreweries, pubs, and restaurants, all just steps away. Enjoy the scenic marina and catch fabulous sunsets at the west end of downtown. Located right across the street from a lively restaurant and bar, this bungalow places you in the heart of the action, making it the ideal spot for your Dunedin getaway. Pet fee is per pet.
4.89 out of 5 average rating, 122 reviews
Pool Home Near Innisbrook Golf & Beaches
Enjoy a relaxing stay in this beautifully renovated 3-bedroom, 2-bath home with a private screened-in pool. Perfect for families, couples, or small groups looking to explore Florida’s Gulf Coast. Located in a quiet area right across the street from the famous Pinellas Trail, you’ll have easy access to biking, walking, and beautiful outdoor scenery. You’re also just minutes from some of the area’s best beaches, restaurants, Innisbrook Golf Resort and attractions.
5.0 out of 5 average rating, 20 reviews
Gulf View on Bay: Newly Renovated
Your cozy getaway awaits in Palm Harbor at this enchanting house. Great view of the Gulf from the living room, back porch and upstairs bedroom. Nice relaxing front deck with rocking chairs. With two spacious bedrooms featuring king beds and a living room that includes a twin bed pullout, guests have plenty of room to relax. The two bathrooms offer both a soothing bathtub and a refreshing shower, perfect for unwinding after a day of adventure.
4.77 out of 5 average rating, 13 reviews
Waterfront Palm Harbor Retreat w/Dock+Near Beaches
Welcome to Island Oasis, your waterfront paradise in Palm Harbor, FL! ☀️🌊 This 3BR, 2BA retreat sleeps 8 and is minutes from Dunedin, Tarpon Springs, and Honeymoon Island. Start your day with coffee on the private dock, explore beaches or bike the Pinellas Trail, then unwind with stunning sunsets over the water. Perfect for families, couples, or friends—come experience true island life in your own slice of paradise! 🌴
5.0 out of 5 average rating, 48 reviews
Pvt Pool, Free Kayaks, Wlk to Gulf, Fish, Bike Trl
Escape to your private Palm Harbor oasis! This studio, offers complete privacy with a cozy queen bed, sofa bed, and kitchenette. Enjoy the sparkling in-ground pool reserved for guests. Walk to the Gulf for fishing, boating, or paddleboarding, or explore the nearby Pinellas Trail. Enjoy beaches, dining, breweries, and live music minutes away. Pet-friendly, with keyless entry and free cleaning for 14+ night stays.
4.99 out of 5 average rating, 128 reviewsPopular amenities for Honeymoon Island holiday rentals
Other great holiday rentals in Honeymoon Island
Studio King Sunset at Beso Del Sol (Pool/Hot Tub)
4.95 out of 5 average rating, 56 reviews
Vacation At Lantana
4.97 out of 5 average rating, 62 reviews
Rooftop+Balcony- Luxury Stay in Downtown Dunedin
5.0 out of 5 average rating, 54 reviews
Sunset Waterfront Paradise | Kayaks, Dock, + Views
4.8 out of 5 average rating, 5 reviews
Rooftop of Dunedin | 8 min to Honeymoon Island
4.94 out of 5 average rating, 16 reviews
Boutique Tiny House Escape with Pool | Sunny
4.95 out of 5 average rating, 39 reviews
Modern Relaxing Coastal 3BR/2BA - Near Beaches
5.0 out of 5 average rating, 29 reviews
Stay, Sip, Stroll · Downtown Palm Harbor
5.0 out of 5 average rating, 16 reviewsFrequently Asked Questions
Where is Honeymoon Island located?
Honeymoon Island is in the Gulf Coast region of Florida, set among barrier islands near the city of Dunedin. The area is known for sandy beaches, nature trails, and coastal ecosystems.
When is the best time to visit Honeymoon Island?
Many visitors choose late winter through spring, when temperatures are mild, typically ranging from 56–83°F (13–28°C), and rainfall is modest. Early summer has warmer days but higher chances of showers, while fall often brings comfortable weather and lighter crowds.
What are some things to do near Honeymoon Island?
Around Honeymoon Island, you can explore nature trails, visit nearby coastal parks, and enjoy kayaking or paddleboarding in calm waters. The local area also has casual dining, small art galleries, and opportunities to learn about local wildlife and habitats.
How is the weather near Honeymoon Island?
Honeymoon Island has warm, humid summers with temperatures usually around 77–91°F (25–33°C), and a greater chance of rain from June through September. Winters are mild and drier, often between 53–74°F (12–23°C), making outdoor activities comfortable year-round.
Destinations to explore
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- Anna Maria Island
- Weeki Wachee Springs
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- University of South Florida
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- MidFlorida Credit Union Amphitheatre
- Sand Key Beach
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- Img Academy
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- River Strand Golf and Country Club
- Busch Gardens
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