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Family Retreat Ocean front pool

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A spa area with a hot tub, a view of the beach, and outdoor seating.
Property video
A two-story hotel with a balcony and a pool area.
A spacious kitchen with a central island, two ceiling fans, and a dining area with wicker chairs.
5 bedrooms, iron/ironing board, WiFi (free)

Reviews

9.4 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 142300 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly

Explore the area

View in a map
Cudjoe Key, FL
  • Place, Upper Sugarloaf Key
    ‪3 min drive‬
  • Place, Upper Sugarloaf Sound
    ‪4 min drive‬
  • Place, Florida Keys Beaches
    ‪8 min drive‬
  • Airport, Key West, FL (EYW-Key West Intl.)
    ‪34 min drive‬

Room options

About the neighborhood

Summerland Key

This vacation home places you within a few miles (5 km) of Upper Sugarloaf Key and Upper Sugarloaf Sound. The vacation home includes a private pool, a kitchen, and a TV.
View more Vacation Homes in Summerland KeyOpens in a new window

What's nearby

  • Upper Sugarloaf Key - 3 min drive - 2.1 miles
  • Upper Sugarloaf Sound - 4 min drive - 2.9 miles
  • Lower Sugarloaf Sound - 7 min drive - 5.1 miles
  • Florida Keys Beaches - 8 min drive - 5.4 miles
  • Great White Heron National Wildlife Refuge - 10 min drive - 5.0 miles

Getting around

  • Key West Intl. Airport (EYW) - 27 min drive

Restaurants

  • ‪Boondock's Grille & Drafthouse - ‬9 min drive
  • ‪Morning Joint - ‬2 min drive
  • ‪Looe Key Tiki Bar & Restaurant - ‬9 min drive
  • ‪The Bent Prop - ‬19 min walk
  • ‪Square Grouper Bar and Grill - ‬2 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.

Family Retreat Ocean front pool

6 Bedroom 4 bath
Rental Rates are based on the number of guests. Base rate is for 6 guests. There is an additional charge of $25 per night per person over 6 guests.
This home can be rented as a 3 bedroom home for a reduced rate or a 6 bedroom home.

Ocean front with pool and a dock for your boat up to 24'

Your property manager lives nearby and is available if you have any requests during your stay

This is a quiet neighborhood in a residential area

This is a private home.
If rented as a 3 bedroom home, guest will have access to 3 bedrooms and 3 bathrooms.
NO OTHER GUESTS WILL BE ON THE PROPERTY.

If rented as a 6 bedroom home, guests will have access to the entire home. 6 bedrooms and 4 bathrooms.

Beautiful Ocean Front Home with six bedroom/Four bath. New memory foam mattresses in King and Queen rooms. Enjoy the heated pool, dock and beach. Located on Cudjoe Bay with panoramic view of the Atlantic and deep water swimming. There are a couple kayaks for your use. You may rent additional kayaks locally. There is a huge screened in porch for your outdoor dining enjoyment. This a very relaxing and beautiful location. There is dining for 12 inside and dining for 6 on the screened in porch. There are several local restaurants within 1-8 miles of the property. Bahia Honda State Park Beach is about 8 miles away. 20 Miles to Key West and all it has to offer. The pool is located beach front with covered lounge area. You can swim and fish off of the dock. we recommend always wearing water shoes when swimming in the ocean.

This home is priced based on the number of guests. The base rate is for up to 6 guests. Additional guests fee is $25 per night per person.


Our Cancellation policy is:
Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be refunded only if we are able to procure another rental for that same period. If no rental is procured, you will lose your payment and any prepaid rent, not to exceed the amount of your rental. If you cancel within 30 days of your arrival, there will be no refund. If The Florida Keys are closed to visitors because of the COVID-19 pandemic for your arrival date, you will be offered the opportunity to reschedule your reservation or receive a refund.

Non-Refundable Damage Deposit Waiver: Instead of charging a security deposit, Host charges a non-refundable $74 damage waiver fee that covers up to $3000 for damage to real or personal property of the vacation rental property as a result of your acts or omissions.

Uber, Lyft and Taxi's area available as well as Public Bus transportation. It is recommended that you have a car

A pet fee and approval of your pet is required.
Prior to your stay we require you to complete a pre-arrival form and sign and agree to our rental conditions.

Pool service and landscaping services may be on the premises during your stay

This home is priced based on the number of guests. The base rate is for up to 6 guests. Additional guests fee is $25 per night per person.


Our Cancellation policy is:
Cancellation: If you cancel your reservation in writing 90 days or more before your arrival, you will receive a full refund, less a cancellation fee of $25.00 and Administrative fee. If you cancel less than 90 days before arrival, your payment and any prepaid rent will be refunded only if we are able to procure another rental for that same period. If no rental is procured, you will lose your payment and any prepaid rent, not to exceed the amount of your rental. If you cancel within 30 days of your arrival, there will be no refund. If The Florida Keys are closed to visitors because of the COVID-19 pandemic for your arrival date, you will be offered the opportunity to reschedule your reservation or receive a refund.

Non-Refundable Damage Deposit Waiver: Instead of charging a security deposit, Host charges a non-refundable $74 damage waiver fee that covers up to $3000 for damage to real or personal property of the vacation rental property as a result of your acts or omissions.
The vacation home is air-conditioned and features a kitchen and 4 bathrooms, and there's space to spread out with 5 bedrooms. Guests can enjoy a TV and stay connected with free WiFi. Other standard amenities include a private pool, a washing machine, and an ironing board.

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Property amenities

Beach

  • On the beach

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Bedrooms

  • 5 bedrooms

Bathroom

  • 4 bathrooms
  • Hair dryer
  • Shower/bathtub combination

Entertainment

  • Games
  • TV

Outdoor areas

  • Garden
  • Porch/lanai

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Things to do

  • Heated pool

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Unit size: 2,300 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 30

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

Rules

NO SMOKING INSIDE - NO PARKING OR DRIVING ON BEACH No parties or events No RV or Motorhome parking

Pets

  • This property welcomes pets
  • Service animals exempt from fees

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
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
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: 30

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • 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 fire extinguisher, a smoke detector, and a first aid kit.

Property is also known as

House
Ocean front with dock heated pool
Ocean Front With Dock Pool hot tub
Now open May 29 June 5 Ocean front with dock heated pool
Ocean front with dock, heated pool great views Cudjoe Key
e5817bc2-0952-4d48-91d8-5042b1bb9491

Frequently asked questions

What can I see near this vacation home?

This vacation home is located in Summerland Key, close to Florida Keys Beaches, Upper Sugarloaf Key, and Sugarloaf Beach. You'll also find Venture Out Keys and Upper Sugarloaf Sound within a short drive.

Is parking available on site at Family Retreat Ocean front pool?

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, this vacation home doesn't have an indoor pool; however, there is a hot tub.

What do couples enjoy most about Family Retreat Ocean front pool?

There are many amenities for couples at this vacation home, including a private pool, a private pool in some house, as well as a beach.

Does Family Retreat Ocean front pool have a hot tub?

No, but guests can enjoy a heated pool 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 free of charge?

Although pets can't stay for free, they are welcome at this vacation home.

Does Family Retreat Ocean front pool have connecting rooms available?

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

How far is the airport from this vacation home?

The closest major airport to this vacation home is Key West Intl. Airport (EYW), which is 19.2 mi away (27 minutes by car). Another top airport is Marathon, FL (MTH-Florida Keys Marathon), which is around 28.4 mi away.

Are there rooms with balconies that I can book at Family Retreat Ocean front pool?

Yes, every house at Family Retreat Ocean front pool comes with a porch/lanai.

Family Retreat Ocean front pool Reviews

Reviews

9.4

Exceptional

Rating 10 - Excellent. 70 out of 95 reviews
Rating 8 - Good. 21 out of 95 reviews
Rating 6 - Okay. 3 out of 95 reviews
Rating 4 - Poor. 1 out of 95 reviews
Rating 2 - Terrible. 0 out of 95 reviews

9.4/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Jane K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location on the water. Spacious house with a nice pool and hot tub
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

Carl N.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was very nice and everyone enjoyed themselves. There was room for everyone and the property and house was beautiful
Stayed 8 nights in Nov 2025
Verified review

10/10 Excellent

Kimberly W.

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

Great Place for Family

The house was great for 3 small families. It was nice to have the pool and a place to dock your boat.
Stayed 7 nights in Jun 2025
Verified review

10/10 Excellent

Glen Y.

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

Great stay

Was a wonderful place to stay met all our needs and then some . What a great week
Stayed 7 nights in Feb 2023
Verified review

8/10 Good

Lorenzo V.

Liked: Cleanliness, check-in, listing accuracy
Amy and team were very responsive and professional! The house was a great location and in nice shape. The dock, hot tub and pool were wonderful to have with a little walk in area into the water. Some negs were the doors and walls were very thin and you're very close to the neighbors so don't expect too much privacy. The positives were the house was very large with all the amenities provided. There were plenty of towels, games
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

MARCEL N.

Liked: Cleanliness, check-in, location, listing accuracy
Disliked: Communication

Great for family

Facility had great space for whole family.
Stayed 6 nights in Nov 2023
Verified review

10/10 Excellent

Laurie F.

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

The location was perfect. Quiet and relaxing.

We would recommend this to others.
Stayed 7 nights in Apr 2023
From a partner site

10/10 Excellent

SusanB

Indeed - A perfect Family Retreat!

We rented only the main 3 BR side to the house. The best equipped kitchen I’ve seen with everything you’d ever need for meal prep. Amazing number of towels provided. Ceiling fans in every room including the amazing screened porch and no issues with AC made for a super comfortable stay. The pool was well maintained and the dock space was perfect. Loved the privacy of this house. An issue with the washer was quickly addressed. I would say the house needs a little TLC but we would definitely stay here again. Would also highly recommend this management company for their personal touch.
From a partner site

10/10 Excellent

Brooks F.

Great Home for Large Families

Plenty of room in the home, great parking for vehicles and boat trailer, great view over Cudjoe Bay to Atlantic, and pool too.
Verified review

10/10 Excellent

Carol M.

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

Very nice place

Clean nice place
Stayed 7 nights in Jan 2023
Verified review

10/10 Excellent

Carol H.

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

Great family getaway!

We very much enjoyed our stay at this spacious comfortable beach house. The six bedrooms suited our needs very well. The pool and the ocean view were wonderful!! The kitchen was large and spacious and had everything we needed. The screened in porch was lovely!!!
Stayed 14 nights in Jun 2025
Verified review

10/10 Excellent

Fiona C.

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

Beautiful view

We had a great time. Looking forward to our return.
Stayed 6 nights in Dec 2021
Verified review

8/10 Good

James J.

Liked: Check-in, location, listing accuracy

Family vacation

Renting went well
Stayed 7 nights in Feb 2023
Verified review

10/10 Excellent

David S.

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

Friends annual reunion

Everything about the house & property were perfect for our group! Amazing house with plenty of room for all. Beautiful ocean view. Pool was a great feature too! Loved our stay.
Stayed 7 nights in Jun 2024
Verified review

10/10 Excellent

James B.

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

New Years get away

We had a great time. We are hoping you can give us a discount so we can come back soon.
Stayed 7 nights in Dec 2023
Verified review

10/10 Excellent

Lisa O.

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

Awesome quiet place close to everything

This home was exactly as advertised, clean, comfortable and provided ample space for 3 couples. Kitchen was well equipped. Pool and hot tub were perfect. Cannot say enough good about this home.
Stayed 7 nights in Apr 2023
Verified review

8/10 Good

Shelly C.

Liked: Cleanliness, check-in, communication, location

Family Vacation

We had a great time at our Cudjoe Key house. The house was clean with lots of room to accommodate a family of 14. The kids, ranging from 2-17 had a great time in the pool, hot tub, fishing and kayaking. Restaurants are a short driving distance as is Key West. Had a great time and would recommend!
Stayed 7 nights in Mar 2024
Verified review

10/10 Excellent

Susan M.

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

Cudjoe retreat

We have stayed here 4 times. Great house . Nice to see some renovation/ improvements made. Kitchen has everything you need for cooking. New mattress were great. Plenty of outdoor activities. Great place to chill either by pool or on lania.
Stayed 7 nights in Mar 2025
Verified review

10/10 Excellent

Michael N Q.

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

Great week!

This property was in a great location! Only 25 minutes to Bahia Honda and 25 minutes to Key West! Our family had a great week! We had just enough room for the 14 of us. The pool was great! Hot tub was great as well! We made use of the Kayaks every day! Would definitely recommend!
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Susan M.

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

Cudjoe retreat

This is the third year we have rented and as always had a wonderful time. Plenty of space for everyone. Enjoyed the screened lanai, and the pool is great. Guys enjoyed fishing on dock. Several good restaurants within a few miles. Square Grouper amazing. Babalu a local was great.
Stayed 7 nights in Feb 2023
Verified review

10/10 Excellent

Amie S.

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

Great Place To Stay on Cudjoe Key!

We loved our stay at the Family Retreat! Plenty of space for everyone, and great views. We enjoyed the hot tub, pool, and the kayaks (and the iguanas everywhere). The house was equipped with all the necessities and accoutrements for cooking. The Squared Grouper is right down the street, jet ski and boat rentals not far either. Only 20 miles to Key West, which is a MUST GO! I recommended this property to anyone looking for a great place to stay with lots of amenities and FUN!
Stayed 7 nights in Jun 2023
Verified review

10/10 Excellent

donna c.

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

Wonderful, quiet and relaxing

Such a great location. Away from the noise and hustle and bustle of Key West, yet close enough to visit and enjoy. Not finding a single bug in a house on the water in FL was a complete miracle! Square Grouper restaurant is only a mile away and is one of the best we have been to. Pool was clean and a wonderful way to stay cool. The screen porch could not be more perfect for morning coffee and dinner. We had a great time, and will be back
Stayed 7 nights in Mar 2023
Verified review

10/10 Excellent

Chan A.

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

Great location and environment

Great property at great location. 3rd year in Cudjoe Keys and second year at the compound. Super open layout with plenty of room both inside and outside. 2 opportunity for improvements - solid bedroom doors recommended. One additional blanket for each bedroom, few used large provided towels during the night. Overall, I would give 4.6 out of 5. Would stay again for sure. Thank you,
Stayed 7 nights in Feb 2025
Verified review

10/10 Excellent

Thomas K.

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

Great Waterfront Key West Home

This house was great for multiple families to have an option to hang out at the pool or do some snorkeling off the dock. Kayaks were a great addition to do a little cruising around the shores. About 20 minutes to Key West. Hot tub was a nice addition as we were down in November and the weather wasn't too hot. Kitchen was well appointed and had extra supplies for somethings we forgot. Little corner store a block over had anything else we were needed in a pinch. Would love to stay here again.
Stayed 6 nights in Nov 2024
Verified review

10/10 Excellent

Verified traveler

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

Great house!

We had an amazing time. PLENTY of room with 6 bedrooms and 4 bathrooms.Pool and dock access was great. Screened porch was wonderful.Only problems were some flying ants that seemed to have hatched while we were there, small bugs that would appear in the bathroom and line the tub between uses, but that's also florida. House also has a TON of towels which came in handy (but we did need some extra blankets which were sparse).Management was also very quick to respond to a problem and it was quickly solved.Thanks! We'll be back!
Stayed 7 nights in Jul 2025

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