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Topsider Resort

3.5 star property
3.5-star beachfront condo with kayaking

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Photo gallery for Topsider Resort

A wooden pier leading to a beach with two houses on either side.
Private beach, sun loungers, beach umbrellas, beach towels
Exterior
Condo, Multiple Beds | Living area | Flat-screen TV, books
Condo, Multiple Beds | In-room dining

Reviews

8.8 out of 10
Excellent

Entire condo

2 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Parking included
  • Free WiFi

Explore the area

View in a map
75500 Overseas Hwy, Islamorada, FL, 33036
  • Place, Sunset Drive Beach
    ‪1 min drive‬
  • Place, Anne's Beach
    ‪3 min drive‬
  • Place, Robbie’s of Islamorada
    ‪3 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪35 min drive‬

Room options

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Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Islamorada
  • On private beach
  • Pool
  • Pet friendly
  • Free WiFi
9.0 out of 10, Wonderful, 218 reviews
$345 nightly
The price is $388
Jul 7 - Jul 8
Total with taxes and fees
Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

About the neighborhood

Islamorada

On the beach.Your stay at this Matecumbe condo places you within 3 miles (5 km) of Sunset Drive Beach and Robbie’s of Islamorada. Anne's Beach and Indian Key Historic State Park are also within 3 miles (5 km).
View more Condo Rentals in IslamoradaOpens in a new window

What's nearby

  • Sunset Drive Beach - 1 min drive - 1.3 miles
  • Anne's Beach - 3 min drive - 2.5 miles
  • Robbie’s of Islamorada - 3 min drive - 2.5 miles
  • Bud n' Mary's Dive Center - 7 min drive - 5.6 miles
  • Florida Keys Brewing Co. - 10 min drive - 7.7 miles

Getting around

  • Miami Intl. Airport (MIA) - 118 min drive

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬3 min drive
  • ‪Lazy Days Restaurant - ‬6 min drive
  • ‪Papa Joe’s Waterfront - ‬6 min drive
  • ‪Islamorada Fish Company - ‬8 min drive
  • ‪Morada Bay - ‬8 min drive

About this property

Entire place

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

Topsider Resort

3.5-star beachfront condo with kayaking
Step outside to unwind on the sand beach. Enjoy the umbrellas and sun loungers for a relaxing day at the beach. After a day at the beach, enjoy amenities at this condo like a marina, an outdoor pool, and an outdoor tennis court.

This beach condo also offers a hot tub, a garden, and a terrace. Free self parking is available.

This 3.5-star Islamorada condo is smoke free.

  • 1 floor
  • 20 guestrooms or units
  • Beach lounge chairs
  • Towels for the beach
  • Umbrellas for the beach
  • Poolside lounge chairs
  • Umbrellas for the pool
  • Self-service laundry
  • Terrace
  • Garden
  • BBQ grill(s)
  • Outdoor picnic space
  • No smoking on site
This condo offers 20 accommodations with coffee/tea makers and irons/ironing boards. Accommodations are furnished with queen sofa beds. Flat-screen televisions are featured in guestrooms. Accommodations at this 3.5-star condo have kitchens with full-sized refrigerators/freezers, stovetops, microwaves, and cookware/dishes/utensils. Bathrooms include bathtubs or showers.

Guests can surf the web using the complimentary wireless Internet access. Business-friendly amenities include phones along with free local calls (restrictions may apply).

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  • On private beach
  • Pool
  • Pet friendly
  • Parking included
4.6 out of 5, Wonderful, 1,343 reviews
$189 nightly
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Total with taxes and fees
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Property amenities

Beach

  • On a private sandy beach
  • Beach loungers
  • Beach towels
  • Beach umbrellas

Pool/Spa

  • Heated pool
  • Hot tub
  • Outdoor pool
  • Pool loungers
  • Pool umbrellas

Internet

  • Available in the condo: Free WiFi

Parking and transportation

  • Free self parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Full-sized refrigerator/freezer
  • Microwave
  • Oven
  • Stovetop
  • Toaster

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Queen sofa bed

Bathroom

  • 2 private bathrooms
  • Bathtub or shower
  • Towels provided

Entertainment

  • Books
  • Flat-screen TV
  • Games

Outdoor areas

  • Barbecue grill
  • Garden
  • Marina
  • Outdoor furniture
  • Picnic area
  • Terrace

Laundry

  • Laundry facilities
  • Washing machine

Climate control

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Free local calls
  • Iron/ironing board
  • No housekeeping service
  • Phone

Location highlights

  • On the bay
  • On the waterfront

Things to do

  • Free bicycle rentals
  • Heated pool
  • Kayaking
  • Outdoor tennis court
  • Fishing nearby
  • Hiking/biking trails nearby
  • Parasailing nearby
  • Scuba diving nearby
  • Snorkeling 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

General

  • 1 floor
  • 20 units
  • Free bicycle rentals
  • Garden
  • Soundproofing

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: 5 PM
Contactless check-in available
Late check-in subject to availability
Minimum check-in age: 21

Check-out

Check-out before 10 AM
Contactless check-out available

Special check-in instructions

The front desk is open Monday - Saturday (8:30 AM - 5 PM)
Guests must contact the property in advance for check-in instructions; front desk staff will greet guests on arrival at the property
To make arrangements for check-in please contact the property at least 72 hours before arrival using the information on the booking confirmation
If you are planning to arrive after 5:00 PM please contact the property in advance using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Staffed front desk

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Cribs (infant beds) are not available.

Smoking

Smoking is not permitted

Property payment types

Important information

Fees

Guests will be asked to pay the following charges at the property:

  • Deposit: USD 150.00 per accommodation, per stay

We've listed all charges provided to us by the property.

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
This property accepts credit cards
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 is professionally cleaned
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 professional host. The provision of housing is linked to their trade, business, or profession. This property accepts Visa, Mastercard, and Discover. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation. The property is professionally cleaned.

We should mention

  • Registered guests are the only ones allowed to be in guestrooms.

Property is also known as

Topsider Resort Islamorada
Topsider Islamorada
Topsider Hotel Islamorada
Topsider Resort Condo
Topsider Resort Islamorada
Topsider Resort Condo Islamorada
Topsider Resort by Capital Vacations

Frequently asked questions

How close is Topsider Resort to the airport?

This condo is 24 mi (32-min drive) away from the Marathon, FL (MTH-Florida Keys Marathon) airport, the closest popular airport to the property.

Does Topsider Resort have an airport shuttle?

Airport shuttle services are not available at this condo.

How close is Topsider Resort to the beach?

This condo is on a private beach. Don't forget your sunscreen!

Does Topsider Resort offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Topsider Resort?

No, there is no casino at this condo.

What time is check-in at Topsider Resort?

Check-in start time: 4:00 PM; Check-in end time: 5 PM.

Is there free parking at Topsider Resort?

This condo offers free self parking.

Does Topsider Resort have a pool?

This condo features an outdoor pool.

Does Topsider Resort have a spa?

There are no spa services available at this condo.

How close is Topsider Resort to downtown Islamorada?

This condo is 6.9 mi away from Islamorada.

Topsider Resort Reviews

Reviews

8.8

Excellent

Rating 10 - Excellent. 40 out of 64 reviews
Rating 8 - Good. 15 out of 64 reviews
Rating 6 - Okay. 5 out of 64 reviews
Rating 4 - Poor. 2 out of 64 reviews
Rating 2 - Terrible. 2 out of 64 reviews

9.0/10

Cleanliness

9.0/10

Staff & service

8.8/10

Amenities

8.6/10

Property conditions & facilities

Reviews

Verified

10/10 Excellent

Rachel

Liked: Cleanliness, check-in, communication, listing accuracy
Quiet, hidden gem in Islamorada—-the friendliest staff and guests. We love the beach, dock for night fishing, and kayaks. Will definitely be back!
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

sal

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
Verified

10/10 Excellent

CHRISTY

Liked: Cleanliness, amenities, property conditions & facilities, communication
Small resort and friendly beautiful views
Stayed 9 nights in Dec 2022
Verified

10/10 Excellent

Daniel A

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
Verified

10/10 Excellent

Nicole

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
Verified

10/10 Excellent

Thomas J.

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
Verified

6/10 Okay

Darlene

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
Verified

8/10 Good

Lupi

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
Verified

10/10 Excellent

Maday

Liked: Amenities
Siempre me gusta este lugar todos los años voy
Stayed 3 nights in Sep 2023
Verified

6/10 Okay

Danya

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
Verified

10/10 Excellent

Taraja

Liked: Cleanliness, amenities, property conditions & facilities, communication
Would definitely come back to stay.
Stayed 3 nights in Feb 2022
Verified

8/10 Good

jeannine o.

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
Verified

10/10 Excellent

Nathan

Liked: Cleanliness, amenities, property conditions & facilities, communication
Our stay at Topsider was outstanding. We will definitely visit again.
Stayed 7 nights in Jan 2022
Verified

6/10 Okay

Alexandre

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
Verified

10/10 Excellent

Levona H.

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
Verified

10/10 Excellent

Jon

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
Verified

10/10 Excellent

Verified traveler

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
Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, amenities, property conditions & facilities, communication
Definitely coming back with my family
Stayed 3 nights in Aug 2021
Verified

10/10 Excellent

Verified traveler

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
Verified

10/10 Excellent

Louisa

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
Verified

2/10 Terrible

Verified traveler

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
Verified

4/10 Poor

Verified traveler

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
Verified

8/10 Good

jasmine h.

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
Verified

2/10 Terrible

Brooke P.

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
Verified

8/10 Good

Tina J.

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