See all properties
Entire home

Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures

Choose dates to view prices

Photo gallery for Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures

Property grounds
Exterior
Property grounds
Smart TV
Marina

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Islamorada, FL
  • Place, Sunset Drive Beach
    ‪6 min walk‬
  • Place, Anne's Beach
    ‪2 min drive‬
  • Place, Bud n' Mary's Dive Center
    ‪9 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪34 min drive‬

Room options

You may also like

Ad

Amara Cay Resort

Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
8.8 out of 10, Excellent, 1,278 reviews
$251 nightly
The price is $283
May 28 - May 29
Total with taxes and fees
Amara Cay Resort

About the neighborhood

Islamorada

Located in Matecumbe within a short walk of Sunset Drive Beach, this vacation home is within a mile (2 km) of Anne's Beach. The vacation home includes a kitchen, a balcony, and a refrigerator.
View more Vacation Homes in IslamoradaOpens in a new window

What's nearby

  • Sunset Drive Beach - 6 min walk - 0.4 miles
  • Anne's Beach - 2 min drive - 1.3 miles
  • Robbie’s of Islamorada - 6 min drive - 4.1 miles
  • Bud n' Mary's Dive Center - 9 min drive - 7.2 miles
  • Florida Keys Brewing Co. - 12 min drive - 9.3 miles

Getting around

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

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬5 min drive
  • ‪Lazy Days Restaurant - ‬8 min drive
  • ‪Papa Joe’s Waterfront - ‬7 min drive
  • ‪The Florida Boy Bar And Grill - ‬8 min drive
  • ‪Habanos Oceanfront Dining - ‬16 min walk

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.
The vacation home is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 3 bedrooms. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

Similar properties

Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room
Amara Cay Resort
Matecumbe
  • On private beach
  • Pool
  • Pet friendly
  • Restaurant
8.8 out of 10, Excellent, 1,278 reviews
$251 nightly
The price is $283
May 28 - May 29
Total with taxes and fees
Amara Cay Resort

Property amenities

Beach

  • Beach nearby
  • Beach towels

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • 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
  • Smoking not allowed

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
  • Snorkeling 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

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 complete the following before checking out:

Load the dishwasher

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

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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 21

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Additional information about polices, regulations, and more:

  • Long-term renters welcome.
  • There are no elevators.

Frequently asked questions

What's there to see around this vacation home?

This vacation home is situated in Matecumbe within a short 20-minute walk of Anne's Beach and also 6 minutes on foot from Sunset Drive Beach. You'll also find Robbie’s of Islamorada and Fiesta Key within a short drive.

Will I be able to park at Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures?

No, there isn't parking at this vacation home.

Is this vacation home next to a casino?

No, this vacation home is not connected to a casino.

Will I find an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

Is Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures a good place to stay for couples?

At this waterfront vacation home, amenities that appeal to couples include a kitchen and a smart TV in each house with some featuring a water view.

Does Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures have a hot tub?

No, there isn't a spa tub at this vacation home.

Does this vacation home offer breakfast?

No, this vacation home doesn't offer breakfast.

Will this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Does Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures have connecting rooms available?

No, there aren't connecting guestrooms at this vacation home.

Where is the closest airport to this vacation home?

The closest major airport to this vacation home is Marathon, FL (MTH-Florida Keys Marathon), which is 22.9 mi away (29 minutes by car).

Can I book a room with a balcony at Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures?

Yes, every house at Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures comes with a balcony and some offer water views.

Dockside Daydream: Where ocean breezes meet unforgettable Keys adventures Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 3 out of 3 reviews
Rating 8 - Good. 0 out of 3 reviews
Rating 6 - Okay. 0 out of 3 reviews
Rating 4 - Poor. 0 out of 3 reviews
Rating 2 - Terrible. 0 out of 3 reviews

10/10

Cleanliness

Reviews

10/10 Excellent

Scott O.

Liked: Cleanliness
Second year in Islamorada so much to do had great weather
Sun set from Marker 88
Stayed 32 nights in Mar 2026

10/10 Excellent

Scott E.

Liked: Cleanliness

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.

Liked: Cleanliness

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