Does Topsider Resort have a pool?

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

Is Topsider Resort pet-friendly?

No, pets are not allowed at this property.

How much is parking at Topsider Resort?

Self-parking is free at this property.

What time is check-in at Topsider Resort?

Check-in start time: 4:00 PM; check-in end time: 5 PM. Late check-in is available during limited hours.

Where is Topsider Resort located?

Nestled on the beach, this Matecumbe condo building is within 3 mi (5 km) of Sunset Drive Beach, Anne's Beach and Robbie’s of Islamorada. Indian Key Historic State Park is 2.5 mi (4 km) away.

Topsider Resort Reviews, Deals & Photos 2025

10/10 Excellent

Daniel A

8 Dec 2022

Liked: Cleanliness, property conditions & facilities, communication

Quaint accommodations with nice beach and pool. Some repairs could be done in the accommodations it is really dated and needs repairs The place is quiet and people are friendly!

Stayed 4 nights in Dec 2022

10/10 Excellent

sal

24 Sep 2025

Liked: Cleanliness, amenities, property conditions & facilities, communication

Unbelievable place with fish swimming near docs. Very comfortable places to stay and very friendly people all around.

Stayed 4 nights in Jul 2025

10/10 Excellent

Thomas J.

21 Feb 2025

Liked: Cleanliness, room comfort, communication

You won't regret it!

Its a great choice for small families looking to relax. Heated pool and hot tub. on property beach access (gulf side). Kayaks and bikes to use. inside the dwelling, master bedroom w/ full bath, another bedroom w/ two twin beds, another full bath, full kitchen + kitchenette, and living room. Really pleased.

Stayed 3 nights in Feb 2025

8/10 Good

Lupi

2 Jan 2025

Liked: Communication

Was happy with our stay as I didn’t have high expectations of it being fancy or modern. We learned that a Topsider is kind of like a treehouse with its main support in the middle underneath which puts you 9-10ft up off the ground. There was some sagging around the outside edges of the structure causing gaps in the flooring and flex with walking around. We loved the simplicity and quietness of this place, the private little beach & dock. All our “neighbors” were kind & respectful with many having ownership in this 20 unit “resort”. Make sure you bring your own shampoo/cond. if you prefer to not use bar soap or dish soap. Hair dryers are also not supplied. The kitchen is well stocked w/dishes, utensils, pots & pans but need to bring your own salt, pepper, oil or anything to cook with. Check-in was easy & proactive communication was appreciated. The beds were quite firm for my liking and bathrooms very small. Good A/C to keep you comfortable. Didn’t use the pool or hot tub as they were sorta out of commission. Glad we got to stay here to end 2024 & start 2025!

Stayed 3 nights in Dec 2024

10/10 Excellent

Maday

2 Oct 2023

Liked: Amenities

Siempre me gusta este lugar todos los años voy

Stayed 3 nights in Sep 2023

10/10 Excellent

Nicole

18 Dec 2022

Liked: Cleanliness, room comfort, communication

Amazing Trip

I absolutely LOVED my stay. I called it my tree house in paradise. Everything you could ask for inside with the fully stocked kitchen. Two bedrooms and 3 bath. It was very clean and super quite.

Stayed 4 nights in Dec 2022

10/10 Excellent

CHRISTY

12 Dec 2022

Liked: Cleanliness, amenities, property conditions & facilities, communication

Small resort and friendly beautiful views

Stayed 9 nights in Dec 2022

6/10 Okay

Darlene

23 Aug 2022

Disliked: Amenities, communication

Location was the best part of the stay. Rooms are very dated. Didn’t know this was a timeshare and I had to change rooms after the first day which was very inconvenient. Have to ask for hair dryer. There is no shampoo or anything other than soap in the rooms.

Stayed 3 nights in Aug 2022

6/10 Okay

Danya

9 Feb 2022

Liked: Amenities, property conditions & facilities

Disliked: Communication

The little condo resort was nice- it had bikes and Kayaks you can use, there was a tennis/ Pickleball court- nice little dock area and a place to sun. Everything was very used but still nice to know it’s available. The court needed to get cleaned off- pool was clean. Decks and stairs all had old peeling paint. But that wasn’t a big deal- just appearances. Overall it’s a decent place.

Stayed 3 nights in Jan 2022

10/10 Excellent

Taraja

8 Feb 2022

Liked: Cleanliness, amenities, property conditions & facilities, communication

Would definitely come back to stay.

Stayed 3 nights in Feb 2022

8/10 Good

jeannine o., Missoula, MT USA

28 Jan 2022

Liked: Cleanliness, location, listing accuracy

Disliked: Communication

Location is very quiet and peaceful

Communication with host company was impossible. They never responded to 3 emails I sent. The area was nice and unit was very spacious and comfortable.

Stayed 3 nights in Jan 2022

10/10 Excellent

Nathan

23 Jan 2022

Liked: Cleanliness, amenities, property conditions & facilities, communication

Our stay at Topsider was outstanding. We will definitely visit again.

Stayed 7 nights in Jan 2022

6/10 Okay

Alexandre, Coconut Grove

29 Nov 2021

Liked: Cleanliness

Disliked: Amenities, property conditions & facilities

The concept of the apartment is good:2 rooms ,2 bathrooms ,One kitchen with lounge. But need renovation and change completely the bathrooms.(at least 40 years old) and painting

Stayed 4 nights in Nov 2021

10/10 Excellent

Levona H.

23 Nov 2021

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

Topsider Birthday Stay

The unit was a two bedroom comfortable stay with a little beach and cookout area! Two bathrooms...very small shower where the single hot tub was...other one was fine. Had a small kitchen that allowed for great breakfasts and a few dinners. Close to great restaurants. Any concerns we had were addressed by management promptly. Daniella was great when we checked in! Nice stay for the two of us and private!

Stayed 4 nights in Nov 2021

10/10 Excellent

Jon

15 Aug 2021

Liked: Cleanliness, room comfort, communication

Topsider was a great little resort

The Topsider was a great little resort - 20 raised 2 BR octagonal-shaped cottages on the property. Our cottage was clean, eqipped with all the kitchen utensils dishes linens we needed. The furniture was in good condition, but the washing machine didnt work. The beach and dock were fine, there were lounge chairs, kayaks and bikes. All in all it was a great deal for the money! I woukd go back.

Stayed 4 nights in Aug 2021

10/10 Excellent

Verified traveller

14 Aug 2021

Liked: Cleanliness, amenities, property conditions & facilities

This place was adorable! We had plenty of space and literally everything we could have needed. The beach/ dock area is pretty busy but everyone was respectful and nice. The pool was never busy- everything we went we were the only ones there!

Stayed 5 nights in Aug 2021

10/10 Excellent

Verified traveller

13 Aug 2021

Liked: Cleanliness, amenities, property conditions & facilities, communication

Definitely coming back with my family

Stayed 3 nights in Aug 2021

10/10 Excellent

Verified traveller

1 Aug 2021

Liked: Cleanliness, amenities, property conditions & facilities, communication

This property is really great for families, especially those with a boat. We felt really safe and secure here and it was close by a lot of food places and shops. We loved the ease of of leaving our boat docked and just heading out to the water. Also loved it having a full kitchen & washer dryer with each unit which helped a lot. We will definitely stay here again.

Stayed 3 nights in Jul 2021

10/10 Excellent

Louisa

18 Jul 2021

Liked: Cleanliness, room comfort, communication

Extremely happy

This place was very clean and the beach was a big plus and Maria from topsider was very nice.

Stayed 3 nights in Jul 2021

2/10 Terrible

Verified traveller

12 Jun 2021

Liked: Cleanliness

Disliked: Amenities, communication

Was promised private beach access, drove 13 hours to get there and an hour before we arrived they called and moved us to another location due to a booking error with no private beach access. Bungalows we’re nice for the price, but everything else including the staff and communication where subpar.

Stayed 3 nights in Jun 2021

4/10 Poor

Verified traveller

5 Apr 2021

Disliked: Cleanliness, communication

Avoid stay over weekend

This is a time share! We had to move rooms due to that we stayed Thu-Sun and they change on Saturdays. No info on this until a couple of hours before check in. And the cleaning was not ok, found dirt on kitchen utensils and cupboards. On top of this, they do not follow their own COVID protocol as there was not a 24 hour window between guests. Did not feel safe.

Stayed 3 nights in Apr 2021

8/10 Good

jasmine h., Indianapolis

30 Mar 2021

Liked: Check-in, location, listing accuracy

Disliked: Communication

communication hell, but gorgeous location

Cons: COMMUNICATION. OMG!! talk about horrid. i was calling for days prior to departure to guarantee our booking. Rarely a call back. Basically, its a time share and then they rent out what doesn't get booked....but...they have to wait until literally the last second to acknowledge a secure reservation. There were other reviews saying this exact thing, so as i started to sense them avoiding me, i knew to be on guard. Arrived and check in was fine....but....that night, i received an EMAIL stating that they were cancelling my reservation. Not an call from them, or a walk to our condo just a few feet away, but an email from VRBO. I called the main office and left a bunch of messages...NONE of which were ever returned. I tried VRBO but the hold was over an hour long and i never got a human on the phone. So we basically spent our vaca in fear of getting kicked out at any moment. (never happened though thank god). Con- not the cleanest place. Main areas and typical things were clean, but around baseboards and inside coffee table needed some attention. Pros- PERFECT location!!!! Private condo with friendly guests. Just a short walk down the boardwalk to their private beach and dock. This was perfect. Snorkeled, kayaked, fished, swam, etc. We caught all kinds of fish and felt very safe swimming around. I would easily make this my "go to" spot if i felt better about the communication with management. One of the longtime guests did say that they think its new owners after Hurricane Erma hit...so maybe its a learning curve. If youre looking for a more private area with out a crowd or a bunch of loud people- this is a great location.

Stayed 3 nights in Mar 2021

2/10 Terrible

Brooke P.

30 Mar 2021

Liked: Cleanliness, location

Disliked: Check-in, communication, listing accuracy

Would have been great....terrible communication!!

Do not book through Vrbo! This place would have been amazing and perfect for the vacation we had planned. Even though we had a trip booked and a reservation confirmed more than 6 weeks in advance, they did not have a place for us when we arrived. Imagine arriving after a day of flying and driving, only to find out that there is no room!! They moved us to their sister resort, over 30 miles away with no beach access! Everything we planned was based on is staying at this specific resort that we booked, so we had to spend most of our trip driving back and forth. Time in the car rather than at the beach! I was never able to get ahold of anyone regarding our reservation so we were completely taken. This is so disappointing for our family and put a large black stain on our vacation. Again, this resort is perfect, had we been able to stay there. Unacceptable business practice!

Stayed 4 nights in Mar 2021

8/10 Good

Tina J., Marshfield, WI

21 Mar 2021

Liked: Cleanliness, check-in, communication, location

Similar to motel

We really enjoyed our stay because it was quiet and not crowded. The pics are a little deceiving because it is an older resort. It was, however, very clean. The downfall for me was the uncomfortable bedding, there were no bathroom amenities, and there was no coffee provided. If you want peace and quiet and no frills, this is perfect for you. My husband and I loved it, but I like to be transparent with what you are getting.

Stayed 4 nights in Mar 2021

8/10 Good

Tara W.

20 Mar 2021

Liked: Cleanliness, location, listing accuracy

Nice units

Nice raised units with own private beach. Good privacy and all the amenities you need right there.

Stayed 3 nights in Mar 2021

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