Title: Topsider Resort - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire condo # Topsider Resort Beachfront, with outdoor pool ## Photo gallery for Topsider Resort ![View from property - Topsider Resort (Islamorada)](https://images.trvl-media.com/lodging/14000000/13280000/13279100/13279004/33888401.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Condo, Multiple Beds | Private kitchen - Topsider Resort (Islamorada)](https://images.trvl-media.com/lodging/14000000/13280000/13279100/13279004/2f1449d7.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Private beach, sun loungers, beach umbrellas, beach towels - Topsider Resort (Islamorada)](https://images.trvl-media.com/lodging/14000000/13280000/13279100/13279004/8cb57036.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Condo, Multiple Beds | In-room dining - Topsider Resort (Islamorada)](https://images.trvl-media.com/lodging/14000000/13280000/13279100/13279004/d0553ca4.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Topsider Resort (Islamorada)](https://images.trvl-media.com/lodging/14000000/13280000/13279100/13279004/w4496h2110x0y0-c9bd9366.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Take advantage of a marina, a terrace, and a garden at Topsider Resort. With a private beach, sun loungers, and kayaking, this condo is the perfect place to soak up some sun. For some rest and relaxation, visit the hot tub. In addition to laundry facilities, guests can connect to free in-room WiFi. ## Reviews 8.8 Excellent ### Entire condo 2 bedrooms2 bathroomsSleeps 6 ## Popular amenities - Pool - Hot tub - Kitchen - Washer - Parking included - Free WiFi ## Add dates for prices Check-in Check-out Travellers ## 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 Beachfront, with outdoor pool At this condo, hit the private sand beach, relax by an outdoor pool, or spend the day at a marina. The condo provides a kitchen with a refrigerator, an oven, a stovetop, and a microwave. Guests can appreciate conveniences like 2 bathrooms and a washing machine, and other amenities include free WiFi and a flat-screen TV. Housekeeping is not available. This condo offers 20 accommodations with coffee/tea makers and irons/ironing boards. 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). A private beach, an outdoor tennis court, a marina, and complimentary bicycles are featured at the condo. An outdoor pool and a hot tub are on site. The recreational activities listed below are available either on site or nearby; fees may apply. ## 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 ### 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 ## Similar properties ![On the beach](https://images.trvl-media.com/lodging/117000000/116460000/116450800/116450740/624144d8.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beachfront Villa w/ Pier & Pool Matecumbe - Pool - Kitchen - Washer - Dryer 6.0 3 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01&selected=116450740&PinnedHotelID=116450740&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/69000000/68980000/68973000/68972962/2cf7160c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Chic Coastal Retreat with Pool, Marina, Beach Access & Resort-Style Amenities Tavernier - Pool - Hot tub - Kitchen - Washer 10 Exceptional 88 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01&selected=68972962&PinnedHotelID=68972962&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/76000000/75630000/75629900/75629846/w1284h1358x0y22-b03c746a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Luxury cottage in the heart of paradise Key Largo - Pool - Kitchen - Washer - Dryer 9.6 Exceptional 28 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01&selected=75629846&PinnedHotelID=75629846&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/88000000/87820000/87810500/87810439/w2300h1284x239y0-25570e88.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### 20 MINUTES TO KEY WEST , BOATERS PARADISE Cudjoe Key - Pool - Hot tub - Kitchen - Washer 9.6 Exceptional 65 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01&selected=87810439&PinnedHotelID=87810439&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/60000000/59930000/59925300/59925243/c5e55a92.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Tropical oasis near all the action with central AC & balcony Duck Key - Kitchen - Washer - Dryer - Air conditioning 8.6 Excellent 38 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2026-01-31&endDate=2026-02-01&selected=59925243&PinnedHotelID=59925243&HadPinnedHotel=true®ionId=-1&adults=2) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/28000000/27080000/27078400/27078385/c366c742.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Reefs, Rods & Unforgettable Sunsets! 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Fees may include applicable taxes: - Deposit: USD 150.00 per accommodation, per stay We have included 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 ### We should mention Only registered guests are allowed in the 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 ## About the area Located on a private beach, this condo is in Matecumbe, a neighborhood in Islamorada. The area's natural beauty can be seen at Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park, while MoradaWay Arts & Cultural District and Keys History & Discovery Center are cultural highlights. Discover the area's water adventures with scuba diving, snorkeling, and parasailing nearby, or enjoy the great outdoors with hiking/biking trails. [Visit our Islamorada travel guide](https://www.expedia.ca/Islamorada.dx10768) [View more Condo rentals in Islamorada](https://www.expedia.ca/Islamorada-Condos.d10768-aaCondos.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C24.86442%2C-80.71500&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=ksvrGmHkp0X9Xsda0717DJEfPMU=) 75500 Overseas Hwy, Islamorada, FL, 33036 ### What's nearby - Sunset Drive Beach \- 1 min drive \- 2.0 km - Anne's Beach \- 4 min drive \- 3.6 km - Robbie’s of Islamorada \- 5 min drive \- 3.7 km - Bud n' Mary's Dive Center \- 10 min drive \- 8.6 km - Florida Keys Brewing Co. \- 15 min drive \- 11.9 km ### Getting around - Miami Intl. Airport (MIA) - 118 min drive ### Restaurants - ‪Hungry Tarpon Restaurant - ‬3 min drive - ‪Papa Joe’s Waterfront - ‬6 min drive - ‪Lazy Days Restaurant - ‬6 min drive - ‪Islamorada Fish Company - ‬8 min drive - ‪The Galley - ‬3 min drive ## Frequently asked questions ### Does Topsider Resort have a pool? ### Is Topsider Resort pet-friendly? ### How much is parking? ### What time is check-in at Topsider Resort? ### What time is check-out at Topsider Resort? ### Where is Topsider Resort located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Topsider Resort Reviews ## Reviews ### Excellent All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 39 8 - Good 14 6 - Okay 5 4 - Poor 2 2 - Terrible 2 ### 9.0 Cleanliness ### 9.4 Location ### 9.0 Staff & service ### 8.6 Property conditions & facilities ## Reviews ### 10/10 Excellent #### Thomas J. Feb 21, 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. ##### Thomas J. Stayed 3 nights in Feb 2025 ### 8/10 Good #### Lupi Jan 2, 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! ##### Lupi Stayed 3 nights in Dec 2024 ### 10/10 Excellent #### sal Sep 24, 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. ##### sal Stayed 4 nights in Jul 2025 ### 10/10 Excellent #### CHRISTY Dec 12, 2022 Liked: Cleanliness, amenities, property conditions & facilities, communication Small resort and friendly beautiful views ##### CHRISTY Stayed 9 nights in Dec 2022 ### 10/10 Excellent #### Daniel A Dec 8, 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! ##### Daniel A Stayed 4 nights in Dec 2022 ### 10/10 Excellent #### Nicole Dec 18, 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. ##### Nicole Stayed 4 nights in Dec 2022 ### 6/10 Okay #### Darlene Aug 23, 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. ##### Darlene Stayed 3 nights in Aug 2022 ### 10/10 Excellent #### Maday Oct 2, 2023 Liked: Amenities Siempre me gusta este lugar todos los años voy ##### Maday Stayed 3 nights in Sep 2023 ### 6/10 Okay #### Danya Feb 9, 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. ##### Danya Stayed 3 nights in Jan 2022 ### 10/10 Excellent #### Taraja Feb 8, 2022 Liked: Cleanliness, amenities, property conditions & facilities, communication Would definitely come back to stay. ##### Taraja Stayed 3 nights in Feb 2022 ### 8/10 Good #### jeannine o., Missoula, MT USA Jan 28, 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. ##### jeannine o. Stayed 3 nights in Jan 2022 ### 10/10 Excellent #### Nathan Jan 23, 2022 Liked: Cleanliness, amenities, property conditions & facilities, communication Our stay at Topsider was outstanding. We will definitely visit again. ##### Nathan Stayed 7 nights in Jan 2022 ### 6/10 Okay #### Alexandre, Coconut Grove Nov 29, 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 ##### Alexandre Stayed 4 nights in Nov 2021 ### 10/10 Excellent #### Levona H. Nov 23, 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! ##### Levona H. Stayed 4 nights in Nov 2021 ### 10/10 Excellent #### Jon Aug 15, 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. ##### Jon Stayed 4 nights in Aug 2021 ### 10/10 Excellent #### Verified traveller Aug 14, 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! ##### Verified traveller Stayed 5 nights in Aug 2021 ### 10/10 Excellent #### Verified traveller Aug 13, 2021 Liked: Cleanliness, amenities, property conditions & facilities, communication Definitely coming back with my family ##### Verified traveller Stayed 3 nights in Aug 2021 ### 10/10 Excellent #### Verified traveller Aug 1, 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. ##### Verified traveller Stayed 3 nights in Jul 2021 ### 10/10 Excellent #### Louisa Jul 18, 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. ##### Louisa Stayed 3 nights in Jul 2021 ### 2/10 Terrible #### Verified traveller Jun 12, 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. ##### Verified traveller Stayed 3 nights in Jun 2021 ### 4/10 Poor #### Verified traveller Apr 5, 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. ##### Verified traveller Stayed 3 nights in Apr 2021 ### 8/10 Good #### jasmine h., Indianapolis Mar 30, 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. ##### jasmine h. Stayed 3 nights in Mar 2021 ### 2/10 Terrible #### Brooke P. Mar 30, 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! ##### Brooke P. Stayed 4 nights in Mar 2021 ### 8/10 Good #### Tina J., Marshfield, WI Mar 21, 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. ##### Tina J. Stayed 4 nights in Mar 2021 ### 8/10 Good #### Tara W. Mar 20, 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. ##### Tara W. 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