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The Caddyshack

Waterfront holiday home with private pool and kitchen

Photo gallery for The Caddyshack

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Pool4 - Caddy Rd
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Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 71750 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space

Rooms & beds

3 bedrooms (sleeps 7)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Double Bed and 1 Single Bed

2 bathrooms

Bathroom 1

Towels provided · Toilet · Shower only · Hair dryer

Bathroom 2

Towels provided · Toilet · Shower only · Hair dryer

Spaces

Garden

About this property

The Caddyshack

Enjoy the spectacular view while unwinding at The Caddyshack.  Relax in the extra large lanai that includes a bar area, a heated swimming pool and even a swim-up bar! The lanai provides havens for both sun and shade, depending on your preference. 

The Caddyshack has an open floor plan and is fully updated inside and out. Gulf coast beaches and state parks, famous for their sunsets, sea shells, sharks teeth and turtle nests, are just minutes away!   

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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
On-site parties or group events are strictly prohibited
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

About the area

Rotonda West

Located in Oakland Hills, a neighbourhood in Rotonda West, this holiday home is next to a golf course and on the waterfront. Whidden's Marina and Boca Grande Lighthouse Museum are local landmarks, and travellers looking to shop may want to visit Port Charlotte Town Center and Sun Flea Market. Tails and Scales Charters and Treasure Lanes are also worth visiting.
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Map
Rotonda West, FL

What's nearby

  • Lemon Bay - 6 min drive - 5.1 km
  • Oyster Creek Golf Club - 6 min drive - 5.8 km
  • Don Pedro Island State Park - 7 min drive - 6.8 km
  • Ann Dever Memorial Regional Park - 7 min drive - 6.8 km
  • Don Pedro Island Beach - 8 min drive - 7.1 km

Getting around

  • Punta Gorda Airport (PGD) - 41 min drive

Restaurants

  • ‪Steamers Oyster Bar - ‬8 min drive
  • ‪Swirls N Curls Ice Cream - ‬7 min drive
  • ‪Nicola's Italian Kitchen - ‬8 min drive
  • ‪Manatee Beans & Brews - ‬7 min drive
  • ‪Rotonda Elks - ‬8 min drive

Frequently asked questions

Does The Caddyshack have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is The Caddyshack pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Caddyshack?

On-site parking is available at the property.

What time is check-in at The Caddyshack?

Check-in begins at 4:00 PM.

What time is check-out at The Caddyshack?

Checkout is at 10:00 AM.

Where is The Caddyshack located?

Located in Oakland Hills, this golf holiday home is 3 mi (4.8 km) from Lemon Bay and within 6 miles (10 km) of Oyster Creek Golf Club and Little Gasparilla Island Beach. Ann Dever Memorial Regional Park and Don Pedro Island State Park are also within 6 miles (10 km).

Reviews

9.8

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 61 out of 66 reviews
Rating 8 - Good. 4 out of 66 reviews
Rating 6 - Okay. 0 out of 66 reviews
Rating 4 - Poor. 1 out of 66 reviews
Rating 2 - Terrible. 0 out of 66 reviews

9.8/10

Cleanliness

10/10

Check-in

10/10

Communication

9.8/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Laura J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great villa. Had everything we needed and wonderful views. Fantastic hosts who would behind helpful and really personable - and went the extra mile for us. Great value for money. Highly recommend.
Stayed 16 nights in Oct 2025

10/10 Excellent

David W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very nice home-had everything we needed and a few extras!
Stayed 6 nights in Jul 2025

10/10 Excellent

Jeffrey H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is as advertised. I would definitely stay again. The pool was wonderful as well!
Stayed 6 nights in Jun 2025

10/10 Excellent

John W.

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

Peaceful

So quiet here... its peaceful!
Stayed 8 nights in Jul 2025

8/10 Good

Roman P.

Liked: Check-in, communication, listing accuracy
Disliked: Cleanliness

Beautiful house, super pool gladly again

Quietly located house with beautiful pool. We had a great time there.
Stayed 17 nights in Jun 2024

10/10 Excellent

Rafael P.

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

Thanks for letting us stayed at your lovely home!!

The house was very clean, all the amenities that you need for a family vacations!!
Stayed 6 nights in May 2023

10/10 Excellent

Tineke S.

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

Redone and fully stocked home

Our family had an amazing stay here, the house is stocked with everything you need for the beach (and there are so many good ones in the area!) With the golf course behind the home felt very private and has a beautiful view. Kitchen, Laundry and Bath were well stocked with many essential supplies.
Bikes available
Sunset at Siesta Key
Stayed 17 nights in Jun 2025

10/10 Excellent

Cami C.

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

10/10

We absolutely loved this home and it was perfect for our family vacation. My daughter loved the pool and the beds were so comfortable! All accommodations were amazing and check in was a breeze!
Stayed 7 nights in Jul 2024

10/10 Excellent

Taylor L.

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

2022 vacation

Loved this home. Hope to stay again soon.
Stayed 6 nights in Jun 2022

10/10 Excellent

John W.

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

Just a great place to stay

Everything was as advertised!! Needed some peace and quiet and this was it! Thanks from our family to yours and we will be coming back next year!
Stayed 7 nights in Jul 2024

10/10 Excellent

Veronica O.

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

Nice getaway

I always enjoy staying in rotonda. This house was wonderful and perfectly accommodated all of us. Plenty of supplies and loved the pay it forward! We even got stuck during a tropical storm and felt safe and comfortable with amazing communication from the owners. Would absolutely stay again!
Stayed 7 nights in Sep 2024

10/10 Excellent

Cheryl L., Granger, IN

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

Perfect Vacation Home for a Family

This home was perfect for our family. Our young adult sons loved both the pool and the golf course. Jack and Pat were the sweetest host and have everything you need to start your stay off right. The house is close to several beaches and restaurants. We will definitely recommend to friends and family!
Stayed 7 nights in Dec 2023

10/10 Excellent

Tonya M.

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

Fabulous Week Away

We were there for a week. The house and pool were amazing. Everything looks exactly as pictured. Highly recommend
Stayed 7 nights in Jul 2024

10/10 Excellent

Tena M.

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

Lovely Pool

The house was just as the pictures and descriptions show. The house had everything we needed. The pool was my favorite place to hangout during the day. There are many good restaurants within 10 to 20 minutes drive from the house. I would definitely recommend this house and if I plan on coming back to this area I would definitely book this property again.
Stayed 6 nights in Apr 2025

10/10 Excellent

Cindy P.

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

Anniversary & Labor Day weekend

Simply Beautiful ❤️
Stayed 4 nights in Aug 2024

10/10 Excellent

Jenna M.

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

Even nicer than photos!

We stayed here six nights and it was perfect for us. We have 2 college age kids each got a room. The main living space had plenty of seating to each do our own thing or things together. The pool was perfect too! Location was between some amazing beaches and some fun restaurants. I'd book again
Stayed 6 nights in May 2024

10/10 Excellent

Judith a.

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

Rotunda home

The property was recently rebuilt after hurricane Ian. Everything was lovely. Owners provided us with many extras like various supplies and were always helpful with our questions. Hope to stay there again.
Stayed 7 nights in May 2023

10/10 Excellent

Tricia S.

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

Lovely Home

This was our second stay at this home. We love this house! I can’t say enough good things about it. The pool is perfect for the kids, nice updates throughout the house, fun view of the golf course! We will come back again soon!
Stayed 7 nights in Jun 2023

10/10 Excellent

George C.

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

PERFECT HOME

This Home was awesome for my family. Close to all the beautiful beaches. The house was clean and with everything you need for your vacation getaway. Beds were super comfortable. The pool was clean and just the right size. Beautiful golf course in the backyard. The owner Pat was great. Thank you again.
Stayed 5 nights in Aug 2023

10/10 Excellent

Klaus-Peter S.

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

Great vacation

Large, renovated house with spacious pool terrace facing south. Large garage with lots of beach gear. 3 bedrooms with comfortable beds, 2 nice bathrooms, master bathroom with rain shower and, really great, a hand shower. Well equipped kitchen with good appliances. Very nice counter table in the window overlooking the pooldeck with expansive views of the golf course, pond and wildlife, great for breakfast with 2 people. Good AC, several fans. The crystal clear pool is a good size and a welcome cool down under the Florida sun. Very nice contact with the host!
Stayed 13 nights in May 2025

10/10 Excellent

Brad R.

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

Great place to relax and unwind

They have about everything you need to enjoy the area, especially the beach. Clothes washer so you can pack light. The host was very attentive and helpful. Nice view behind the house with a little wildlife. Even had a crane walk right up by the backyard one morning. Will go back.
Stayed 6 nights in Aug 2023

10/10 Excellent

Denise B.

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

Family time

We booked this property early spring. We were nervous about booking due to damages during hurricane Ian last fall. We were able to communicate with the owers Jack and Pat. They communicated all was well with the property. We would definitely recommend this property. It was very close to the beach. The neighborhood was quite and the kids loved the home and pool. The kitchen was well stocked with items to prepare meals. We would definitely book again.
Stayed 6 nights in Jun 2023

10/10 Excellent

Bonnie M.

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

Great Vacation

We recently stayed at this home. Very nice home that has been updated. Great for 2 families as there are 2 very separate sleeping areas. Close to fabulous beaches (Boca Grande was amazing), shopping, grocery stores, punta gorda airport. A nice walking/biking trail nearby that includes a walking/bike trail in the park for a 4 km jaunt. House is very well stocked to prepare meals. Lots of recreational items in the garage like umbrellas, bikes, beach chairs etc that was great! Heated pool was very nice. Pat and Jack are excellent hosts who we got to meet while we were there. Don't hesitate to rent this property.
Stayed 28 nights in Nov 2023

10/10 Excellent

Clare G.

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

Just perfect!

We couldn’t want for anything more. The house was everything and more. Excellent information provided ahead of our arrival and when we arrived we felt at home immediately. We made use of the ideas of places/beaches to visit that were sent to us. Might be worth mentioning that most of the beach car parks have a variety of charges. The property is beautifully maintained and well equipped with everything we could possibly need. We loved the pay it forward ethos and made sure we continued that. We made use of the beach chairs and umbrellas (most welcome!), cooler and the bikes. We loved sitting in the pool watching the golfers pass by and we did go and play a round on the course. We’ve been to Rotunda previous (albeit 15yrs ago) and it didn’t disappoint. We came away with our mission to relax and have fun and this was firmly achieved. We would love to come back in the future with the rest of the family.
Stayed 8 nights in May 2024

10/10 Excellent

Kai K.

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

Toller Familienurlaub

Alles war wie erwartet.Das Haus ist modern und schön eingerichtet. Alle drei Betten waren super bequem. Uns gefiel sehr gut der erste Kaffee an Morgen und diese Ruhe durch den Gofplatz. Sehr viele Vögel waren dort unterwegs und die Golfer störten uns gar nicht. Die Vermieter Pat und Jack kümmerten sich gut um uns. Wir hatten ein kleines Problem mit einer Dusche. Jack kam am nächsten Tag und half uns.
Stayed 15 nights in Oct 2024

About the host

Hosted by Jack and Pat Fuhrmann

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English

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