Entire home·Private host

Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures

Waterfront holiday home with kitchen and balcony

Marina - Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures (Islamorada)

Property grounds - Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures (Islamorada)

Experience the ultimate tropical paradise at this charming Islamorada waterfront property. Unwind in a tranquil atmosphere with a full kitchen, washer/dryer, and kayaks to explore the canal. Enjoy outdoor activities like fishing off the dock or lounging by the above-ground pool overlooking the water.

Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 8

Popular amenities

Parking available
Dryer
Washer
Barbecue grill
Kitchen
Air conditioning

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures

Dockside Daydream – Waterfront Paradise in the Florida Keys
Welcome to Dockside Daydream, your tropical escape in the heart of the Florida Keys. This 3-bedroom, 2-bath waterfront retreat blends laid-back island charm with modern comfort, offering the perfect setting for both relaxation and adventure.
Features:
• Prime Waterfront Location – Wake up to sparkling water views and gentle ocean breezes.
• Private Dock & Boat Ramp – Launch your boat, kayak, or paddleboard right from the backyard.
• Private Beach Access – Enjoy sun-soaked days and unforgettable sunset views on your own stretch of sand.
• Outdoor Living – Spacious deck and patio for lounging, dining, and sunset cocktails.
• Island Style Interiors – Bright, airy spaces with coastal-inspired décor.
• Fully Equipped Kitchen – Cook up fresh Keys seafood with ease.
• Comfortable Bedrooms – Cozy, inviting spaces designed for restful nights.
Perfect For couples seeking romance, families craving fun in the sun, or friends ready for a Keys adventure. Whether you’re snorkeling, fishing, boating, or simply unwinding by the water, Dockside Daydream is your gateway to unforgettable memories.

Property amenities

Beach

Beach nearby
Beach towels

Internet

Available in the house: Free WiFi

Parking and transport

Parking on site

Kitchen

Blender
Coffee/tea maker
Cookware, dishware, and utensils
Dishwasher
Hob
Microwave
Oven
Paper towels
Refrigerator
Toaster

Dining

Dining table

Bedrooms

3 bedrooms
Bedsheets provided

Bathroom

2 bathrooms
Bathtub or shower
Hair dryer
Shampoo
Shower
Soap
Toilet paper
Towels provided

Living spaces

Dining table
Living room

Entertainment

Games
Smart TV

Outdoor areas

Balcony
Barbecue grill
Outdoor furniture

Laundry

Laundry facilities
Washing machine

Comfort

Air conditioning
Heating

Pets

No pets allowed

Suitability/Accessibility

If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
Upper floors accessible by stairs only
Smoke-free property

Services and conveniences

Iron/ironing board

Location highlights

Near the bay
Near the marina
On the waterfront

Things to do

Kayak
Cycling nearby
Fishing nearby
Jet skiing nearby
Kayaking nearby
Motor boating nearby
Scuba diving nearby
Snorkelling nearby
Swimming nearby
Water tubing nearby

Safety features

Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher

Similar properties

Pool
Kitchen
Washer
Dryer

Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Check-out instructions

The host requires you to complete the following before checking out:

Load the dishwasher

Remove personal items, remove leftover food and drinks and take out the rubbish

Turn off the lights, lock the doors and return the keys

Failure to complete these may result in a negative review from the host.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

On-site parties or group events are strictly prohibited

Long-term renters welcome

Host has indicated that there is a carbon monoxide detector on the property

Host has indicated that there is a smoke detector on the property

Safety features at this property include a fire extinguisher

This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

This property does not have any lifts

About the area

Islamorada, FL

What's nearby

Sunset Drive Beach - 6 min walk - 0.5 km
Anne's Beach - 3 min drive - 1.7 km
Robbie’s of Islamorada - 7 min drive - 5.9 km
Bud n' Mary's Dive Center - 12 min drive - 10.9 km
Florida Keys Brewing Co. - 17 min drive - 14.2 km

Getting around

Marathon, FL (MTH-Florida Keys Marathon) - 29 min drive

Restaurants

‪Hungry Tarpon Restaurant - ‬5 min drive
‪Papa Joe’s Waterfront - ‬7 min drive
‪Lazy Days Restaurant - ‬8 min drive
‪The Galley - ‬18 min walk
‪The Florida Boy Bar And Grill - ‬8 min drive

Frequently asked questions

Is Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures pet-friendly?

No, pets are not allowed at this property.

How much is parking at Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures?

On-site parking is available at the property.

What time is check-in at Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures?

Check-in begins at 4:00 PM.

What time is check-out at Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures?

Checkout is at 10:00 AM.

Where is Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures located?

Located in Matecumbe, this holiday home is within 1 mile (2 km) of Sunset Drive Beach and Anne's Beach. Robbie’s of Islamorada and Indian Key Historic State Park are also within 6 miles (10 km).

Have a question?

Get instant answers with AI powered search of property information and reviews.

Ask a question

Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures Reviews

10

Exceptional

10

Cleanliness

10

Location

10/10 Excellent

Scott E.

4 Apr 2025

Liked: Cleanliness, check-in, communication, location, listing accuracy

Venetian Drive vacation

Excellent accommodations. Clean and neat. Nice dock for a boat. Will stay again next year.

Stayed 30 nights in Feb 2025

10/10 Excellent

David D.

11 Feb 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice and clean

Nice place. And we loved the stay but we hate the way the rental agencies throw in a bunch of bs add on charges but that s not the owners fault. We have been wintering it in the Keys for decades and the extra charges did not used to be like that. Just one example: you have to pay 600 or 700 dolars for a fee in case something breaks to have 24 hour service with no way to opted out of that fee or no refund if it's not use. Which we think that should be the owners responsibility.

Stayed 35 nights in Dec 2023