See all properties
Entire home

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Enjoy the outdoor pool at this beachfront Islamorada vacation home

Choose dates to view prices

Photo gallery for Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

On the beach, sun loungers, beach towels
Smart TV
Fridge, microwave, oven, stovetop
Smart TV
Terrace/patio

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 102450 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer

Explore the area

View in a map
Islamorada, FL
  • Place, Robbie’s of Islamorada
    ‪1 min drive‬
  • Place, Indian Key Historic State Park
    ‪1 min drive‬
  • Place, Bud n' Mary's Dive Center
    ‪4 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪38 min drive‬

Room options

You may also like

Ad
Balcony view

Hadley Resort and Marina

Matecumbe
  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
3.8 out of 5, Good, 1,003 reviews
$175 nightly
The price is $197
Jun 15 - Jun 16
Total with taxes and fees
Hadley Resort and Marina

About the neighborhood

Islamorada

On the beach.With a stay at this Matecumbe vacation home, you'll be within half a mile (1 km) of Robbie’s of Islamorada and 2 miles (3 km) of Indian Key Historic State Park. San Pedro Underwater Archaeological Preserve State Park and Sunset Drive Beach are also within 3 miles (5 km).
View more Vacation Homes in IslamoradaOpens in a new window

What's nearby

  • Robbie’s of Islamorada - 1 min drive - 0.5 miles
  • Indian Key Historic State Park - 1 min drive - 1.1 miles
  • Bud n' Mary's Dive Center - 4 min drive - 3.5 miles
  • Sunset Drive Beach - 4 min drive - 3.3 miles
  • Anne's Beach - 6 min drive - 4.6 miles

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 32 min drive

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬7 min walk
  • ‪Lazy Days Restaurant - ‬4 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬7 min drive
  • ‪Papa Joe’s Waterfront - ‬3 min drive
  • ‪Wendy's - ‬7 min drive

About this property

Entire place

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

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views

Gorgeous 30’ oceanfront heated pool. House on an exceptionally private, natural beach and oceanfront seawall in Islamorada - observation dock for paddle boarding, fishing and kayaking. Property is flanked by natural preserve on one side and has wide open expansive ocean views. The private beach is located along a wildlife protected turtle nesting beach that left natural for turtle nesting season.

There is an incredible 180 degree water view from almost every room in the house. Spectacular sunrises flood the rooms with golden light reflected off the ocean. The sun rises over the water every morning within your view. The sunsets are equally stunning over the peninsula leaving the view with purple and pink clouds. Constant onshore breeze drifts through the house with pure, invigorating ocean scents.

2 Paddle boards and 2 kayaks are included with rental as the waters off the house are perfect for exploring by kayak. 2 cabanas for rest and relaxation - one by the pool and one the dock. The wildlife is stunning and you are bound to see amazing creatures during each outing! There is also an amazing State Park (an island) just a paddle away. Alligator Reef Lighthouse is on the horizon and the ocean views from the end of the observation dock are simply incredible. The oceanfront pool is heated to 86 degrees.

The house is a 100% non-smoking property. The observation dock is for non-motorized vessels only as the tides can get very low during full moons.

THIS PROPERTY RENTS SATURDAY TO SATURDAY
Robbie's of Islamorada is down the street from the property a half mile and offering an outdoor restaurant, jet ski rentals, tarpon feeding, shops, fishing charters, snorkeling trips & sunset cruises to the Lighthouse.

About the owner: Islamorada is absolute paradise - we love the island and happy to share the vacation house with guests looking to escape to a patch of paradise in the Keys. The is property is exclusively offered as a vacation rental so it is similar to staying at a hotel and is exceptionally clean and easy to enjoy.

We privately own a total of 5 boutique vacation rentals in Islamorada:
VRBO listing #1576833 (5 bedroom)
VRBO listing #1054019 (5 bedroom)
VRBO listing #1977457 (7 bedroom)
VRBO listing #689629 (5 bedroom)

(no boat dockage due to tides)

LICENSE #: 26-0279 - Islamorada

Similar properties

Private beach, white sand, sun loungers, beach towels
Chesapeake Beach Resort
Matecumbe
  • On private beach
  • Pool
  • Breakfast included
  • Pet friendly
4.6 out of 5, Wonderful, 1,736 reviews
$240 nightly
The price is $270
Jun 8 - Jun 9
Total with taxes and fees
Chesapeake Beach Resort

Property amenities

Beach

  • On the beach
  • Beach loungers
  • Beach towels

Pool/Spa

  • Heated pool
  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Kitchen island
  • Lobster/crab pot
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Spices
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 5 bathrooms
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill
  • Firepit
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a hospital
  • Near the ocean
  • On the waterfront

Things to do

  • Heated pool
  • Kayak
  • Water sports equipment
  • Birdwatching nearby
  • Fishing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Sailing nearby
  • Snorkeling nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Windsurfing 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 2,450 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Minimum check-in age: 24

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 and start the dishwasher

Take out the trash

Lock the doors

Please be sure to put recycling out in the bin WITHOUT a bag - the trash service will not pick up the bin if the contents are bagged.

Please leave the towels hanging and the sheets on the beds.

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

Rules

Absolutely no smoking, no access to the rooftop.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

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
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, a first aid kit, and a deadbolt lock
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    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. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock in each accommodation.

Property is also known as

Amazing Oceanfront Paddleboards Kayaks 180 Degree Ocean Views

Amazing Oceanfront Paddleboards Kayaks 180 degree ocean views

Frequently asked questions

How close is Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views to the airport?

This vacation home is 25.5 mi (32-min drive) away from the Marathon, FL (MTH-Florida Keys Marathon) airport, the closest popular airport to the property.

Does Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views to the beach?

This vacation home is on the beach. Don't forget your sunscreen!

Does Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views?

No, there is no casino at this vacation home.

What time is check-in at Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views?

Check-in begins at 4:00 PM.

Is there free parking at Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views?

Free parking is not available at this vacation home.

Does Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views have a pool?

This vacation home features an outdoor pool.

Does Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views have a spa?

There are no spa services available at this vacation home.

How close is Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views to downtown Islamorada?

This vacation home is 5.2 mi away from Islamorada.

Private Oceanfront: Heated Pool, Paddleboards & Kayaks - 180 degree ocean views Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 115 out of 116 reviews
Rating 8 - Good. 1 out of 116 reviews
Rating 6 - Okay. 0 out of 116 reviews
Rating 4 - Poor. 0 out of 116 reviews
Rating 2 - Terrible. 0 out of 116 reviews

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Joe T.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay! The Property is beautiful and the host added some great personal touches to made our stay outstanding.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Jody H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was perfect. Beds comfortable, the pool was clean and perfect temperature. It felt like being home.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Susan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The location is fabulous. A beautiful, private well situated house and property. We enjoyed the pool, kayaks and paddle boards, fire pit and the dock. A wonderful place to spend time with family… 5 bedrooms with private baths gave everyone the space they needed. We would definitely return to this rental.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Kelli K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was extremely welcoming! Amenities were comprehensive. House is beautiful and great location.
Stayed 7 nights in Dec 2025
Verified

10/10 Excellent

Laura R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The host was fantastic! Very prompt and accommodating, super friendly! The place was super clean, and it had everything we needed! The views were spectacular, the pool was great, and we are definitely considering coming back again next year.
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

Sarah A.

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

Amazing Host & Beautiful Property!

We had the best time relaxing in paradise at this magnificent home!
Stayed 7 nights in Apr 2025
Verified

10/10 Excellent

Sharon H.

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

Excellent property

We had a great time the property was perfect
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Laura W.

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

Amazing house and great vacation spot!

We loved everything about this house! The outdoor areas were perfect. We had everything we needed to have a great time at the house but close enough to venture out and explore the keys if we wanted. Owners were responsive and great to work with
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Chip W.

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

Great week in Islamorada!

The property was a perfect fit for our three family spring break. Plenty of ways to relax and enjoy the property and great location to all that Islamorada and the surrounding area has to offer. Super friendly and attentive hosts, a well appointed property and a view that we’ll never forget.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

richard t.

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

Great trip

Nice property.. great views..close to stores.. activities..etc…privacy.. excellent!
Stayed 7 nights in Apr 2023
Verified

10/10 Excellent

lauren p.

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

Great vacation in the keys

Very nice house with amazing views of the water and close to many activities
Stayed 7 nights in Mar 2020
Verified

10/10 Excellent

Craig R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Chauncey was awesome and very accommodating.
Stayed 7 nights in Jun 2025
Verified

10/10 Excellent

Lindsay T.

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

Perfect home in paradise!

We absolutely love Islamorada and this house and location could not have been more perfect for our family!
Stayed 7 nights in Jul 2022
Verified

10/10 Excellent

Trent L.

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

Stop looking and book this place before its too late

This place has something for everyone, the rest of the reviews are spot on.
Stayed 7 nights in Jan 2023
Verified

10/10 Excellent

Sarah F.

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

Fabulous Islamorada

We loved our stay at Luna House. Plenty of beds and room to spread out inside and outside. It is next to a nature preserve, so quiet and peaceful!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Robert A.

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

GREAT SPOT!

The property manager is very prompt and accommodating. The place was as advertised and will stay again next time in the Keys.
Stayed 13 nights in Jun 2019
Verified

10/10 Excellent

Sherri D.

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

Beautiful Home

This is the perfect location and home for a large gathering. 5 bedroom suites that offer privacy for each room, beautifully well stocked kitchen and everything you need for outdoors. Highly recommend!
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Carol E.

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

Family trip

The house, pool, and amenities were all wonderful. Lots of space for the whole family! Loved being right on the ocean. Plenty of restaurants and water activities nearby.
Stayed 7 nights in Jun 2023
Verified

10/10 Excellent

Jacquelyn R.

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

Family vacation

Perfect space for our family of four couples and one single. Enough privacy with 5 beds and bathrooms but plenty of communal space. The pool was a highlight. We also loved all the outdoor seating options. Chausey responded quickly with a new coffee maker when the original one wouldn't work.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Lisa B.

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

AMAZING PROPERTY!!!!

This property was like a mini resort! The house itself was very clean and spacious. Kitchen was well stocked. We REALLY enjoyed our stay!
Stayed 7 nights in May 2023
Verified

10/10 Excellent

Sherri D.

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

Beautiful home and location

This is an easy house to kill time. Beautiful views, comfy furnishings, pool and beach loungers. Just lovely.
Stayed 7 nights in Jan 2023
Verified

10/10 Excellent

April A.

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

Wonderful!!

Words cannot describe; wonderful!!
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

A W.

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

THE AMAZING VIEWS

The amazing views are great!!!! Wonderful house, was great for 3 couples with 2 bedrooms downstairs having their own living area and private baths. House pretty equipped with all your needs and games. Not far from some great restaurants, Publix.
Stayed 7 nights in Jun 2024
Verified

10/10 Excellent

Maria T.

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

Excellent property! Beautiful views!

House was beautiful, clean and comfortable for our family of 9! Location was excellent and close to many things to do. It was easy to jump on trail across the street and ride bikes and we enjoyed using the kayaks. The heated pool was excellent and so relaxing! We would come back to stay here again. Highly recommend!!! PS Owner was very responsive and easy to work with!
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Craig R.

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

Vacation 2023

Awesome view.
Stayed 7 nights in Jun 2023

Explore More Ways to Travel with Travelocity