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Bayside - Islamorada Waterfront, 360 Viewing Deck, Htd Swim Spa

Bedrooms: 5

Bathrooms: 3

Sleeps: 10

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Overview ↑↓

THE SPACE

Welcome to Bayside, a spacious Islamorada waterfront vacation rental designed for sunset views, outdoor living, and relaxed Florida Keys stays. This 2,677-square-foot canalfront home spans multiple floors and features a rooftop 360° viewing deck with canal, bay, ocean, and sunset views. With a dock and boat lift available by request ($750 per stay), guests can enjoy easy boating access and reach the famous Islamorada Sandbar within minutes by boat.

The main living area is located on the second floor and is accessed by an exterior staircase at the front of the home. Inside, guests will find a comfortable layout with a spacious kitchen, dining area, living room, desk space within a bedroom, and easy access to the screened balcony and outdoor areas.

With inviting spaces to dine, unwind, and take in the waterfront views, Bayside offers a relaxed Islamorada setting made for memorable days and easy evenings by the water.

⭐ WHAT YOU’LL LOVE

✔ Canalfront Islamorada vacation rental with sunset-facing views
✔ Rooftop 360° viewing deck with canal, bay, and ocean views
✔ Heated swim spa/hot tub, outdoor kitchen, gas grill
,✔ Spacious 5-bedroom layout with 3 full bathrooms
✔ Close to Anne’s Beach, Robbie’s, multiple restaurants, and ocean access via your boat

️ KITCHEN + LIVING SPACE

The kitchen is spacious and designed for gathering, with modern appliances, cooking essentials, drip coffee maker, Keurig, a dining table for eight, and counter seating with stools.

The kitchen opens into the main living area, where guests can relax with comfortable seating and a 65-inch TV.

️ BEDROOMS + SLEEPING ARRANGEMENTS

All bedrooms include premium beds, linens, and storage space.

♛ Primary Bedroom Second Floor: King-size bed, ensuite bathroom, and walk-in closet

Bedroom 2 Second Floor: Two twin beds. The full bathroom is accessible from this bedroom and the hallway.

Bedroom 3 Third floor: Two twin beds, a small sofa, armoire, and balcony access.

Bedroom 4 Third Floor: Queen-size bed, TV, ensuite bathroom, and walk-in closet

Bedroom 5 Second Floor: Daybed with trundle, desk, and armoire.

BATHROOMS

Bathrooms are stocked with essentials including shampoo, conditioner, body soap, and fresh towels.

Primary Ensuite: Full bathroom, standing shower, connected to the primary bedroom on the second floor

Second-Floor Bathroom: Full bathroom, standing shower, accessible from Bedroom 2 and the hallway

Queen Bedroom Ensuite: Full bathroom, shower/tub combo, connected to the queen bedroom on the third floor

OUTDOOR SPACE

The outdoor areas are one of Bayside’s strongest features. Guests can enjoy a heated swim spa/hot tub, outdoor kitchen with ceiling fan, gas grill, dining table for 10, screened balcony, patio, yard, sun loungers, dock, and multiple seating areas.

The rooftop 360° viewing deck offers wide-open canal, bay, ocean, and sunset views, creating a memorable place to take in the Islamorada waterfront setting.

WATERFRONT + BOAT LIFT

Bayside is located on a canalfront lot with waterfront views and a short ride via channel 2 bridge to ocean access and the Islamorada Sandbar.
-Boat lift use may be available by request only for $750 per stay. The lift can accommodate boats up to 35’. Without lift use, the maximum boat size allowed is 30’. Guests must request boat lift use at the time of booking, and approval is required in advance.

PARKING + ARRIVAL

The driveway offers parking for up to 4 cars.

Guests enter the home using the exterior staircase at the front of the property, which leads to the second-floor main living area.

NEIGHBORHOOD OVERVIEW

Located in Islamorada, Bayside places guests close to beaches, restaurants, boating, fishing, snorkeling, kayaking, paddleboarding, and local Florida Keys attractions.

Anne’s Beach is about half a mile away. Guests can also bike or take a short drive to Robbie’s, and nearby restaurants.

POINTS OF INTEREST
Distance measured in approximate driving time, non-rush hour.

-Anne’s Beach (2–3 min / about 0.5 mile): Shallow water, boardwalks, picnic areas, and a relaxed shoreline setting

-Robbie’s of Islamorada (6–8 min): Tarpon feeding, boat tours, watersports, shopping, and casual waterfront dining

-Morada Bay (10–12 min): Beach cafe, sunset views, cocktails, dining, and local events

-Papa Joe’s Waterfront (10–12 min): Waterfront dining, tiki bar, lawn area, and sunset views

-Lazy Days Restaurant (10–12 min): Oceanfront dining, seafood, drinks, and classic Keys atmosphere

-Bud N’ Mary’s Marina (10–12 min / approx. 6 miles): Fishing charters, marina services, and a well-known Islamorada boating destination

-Publix Super Market (13–15 min): Convenient grocery store for food, drinks, and vacation essentials

-Founders Park (18–22 min): Beach access, pool, playground, sports fields, and outdoor recreation

-Islamorada Sandbar (by boat): One of the area’s most popular boating destinations; travel time varies by route, weather, and launch point

⚠️ IMPORTANT THINGS TO NOTE

-This property is not pet friendly.

-Guests do not have access to the garage or ground-level apartment.

-Guests do not have access to elevator

-The owner’s boat is located on-site and must not be touched, boarded, moved, or used at any time.

-Highchair available

-Washer and dryer provided for maximum convenience

HOUSE RULES

Check-in time: 4:00 PM
Check-out time: 10:00 AM

-All guests must sign our rental agreement as required by Florida law.

-Minimum booking age is 25. A valid photo ID is required after booking.

-An accurate guest count must be provided before arrival.

-Pets are NOT permitted.

-No smoking or vaping is allowed inside the home or on the property.

-No parties or events are permitted. Unauthorized guests on the property may result in additional fees and/or immediate eviction.

-The owner’s boat is located on-site and must not be touched, boarded, moved, or used at any time.

-Quiet hours are from 10:00 PM to 8:00 AM.

RELEASE OF LIABILITY FOR AMENITIES

Guests use all amenities, outdoor areas, balconies, rooftop deck, swim spa/hot tub, and recreational items at their own risk. Children must be supervised by an adult at all times. The property management company and owners are not liable for any injuries, damages, or losses related to their use.

STARTER SUPPLIES

We provide starter supplies including trash bags, paper towels, toilet paper, detergent, and bathroom amenities to accommodate the home’s maximum occupancy for the first three days of your stay.

SAME-DAY BOOKINGS

Same-day bookings require company approval. Guests must provide information about their group and purpose of stay. If approved, a government-issued ID is required for verification. Your phone number must match the phone number registered on your account, or your reservation cannot be honored.

Same-day reservations will not be accepted after 2:00 PM. All same-day bookings require a minimum of 3 hours before check-in, and check-in may be extended later than 4:00 PM.

Amenities ↑↓

Changeover/Arrival Day

24Hr Check-In

Amenities

Air Conditioning, Conditioner, Dryer, Essentials, Extra Pillows And Blankets, Hair Dryer, Hangers, Internet, Iron, Iron Board, Linens, Linens provided, Living Room, Parking, Parking space Accessible, Private Entrance, Self Check-In, Shampoo, Smartlock, Towels, Towels provided, TV, Washer

Outdoor

Balcony, Balcony/Terrace, Deck Patio Uncovered, Garden Or Backyard, Grill, Patio, Patio Or Balcony, Sun roof/roof terrace, Terrace

Safety Features

Carbon Monoxide Detector, Deadbolt Lock, Fire Extinguisher, First Aid Kit, Outdoor Lighting, Smoke Detector

Cleanliness

Cleaning Disinfection, Enhanced Cleaning Practices, High-touch surfaces cleaned with disinfectant, Self Check In / Check Out

Sports and Adventure

Fishing Bay, Fishing nearby, Golf course within 30 min drive, Kayaking, Snorkeling, Snorkeling / Diving, Swimming, Tennis courts nearby, Watersports nearby

Entertainment

Laptop Friendly, Television

Car

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