Smoke-free property

Garden

Terrace

Outdoor furniture

General

Laundry

Services and amenities

Barbecue grill(s)

Hiking

Picnic area

Barbeque

Sun Deck

Recreation

Free parking

Parking

Pool facilities

Pool and beach

Pets Not Allowed

Pets

Extra decontamination measures

Contactless check-in and/or check-out

Health and Safety Measures

Location

At the resort

Sunset Drive Beach

Florida Keys Marathon Airport

Topsider Resort

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

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.

PERFECT LOCATION for a relaxing family trip to the Keys.  Only 20 units, each with its own private balcony (thanks to the mature, lush tropical greenery), 2 beds/2 baths, open kitchen/living/dining area.  We had a few sunny days and a few rainy ones so having the living area was great and we grabbed a Monopoly game from the office and played all afternoon.  We used the charcoal grill outside the unit to grill up some steaks and having the full kitchen helped us save money with eating in for breakfast and lunch.  Nice sandy beach with lounge chairs, dock for fishing and mooring your boat, free use of kayaks and bikes meant that our teens were kept busy and happy.  Each unit has a (free) washer/dryer so we could pack less.  Unit had plenty of towels for showering and an extra set for the beach.  If you want no muss/no fuss this is it!  We will be back!

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.

Small resort and friendly beautiful views

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!

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

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!

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.

Islamorada

child-bed

child-bed-fee

external-private-bathroom

private-bathroom

shared-bathroom

10-beds

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king-bed

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limited-time

lounge

treatment

no-window

bay-view

bosphorus-view

canal-view

city-view

courtyard-view

garden-view

golf-view

harbour-view

inland-view

lake-view

land-view

mountain-view

ocean-front

ocean-view

oceanside

panoramic-view

park-view

partial-ocean-view

partial-sea-view

partial-view

pool-view

river-view

sea-front

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with-view

annex

basement

main-building

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6 bedrooms

not-guaranteed

wired-internet-access

smoking

sauna

duplex

safe

mini-bar

breakfast-for-1

breakfast-for-2

pets-allowed

wi-fi

park access

You won't regret it!

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!

PERFECT LOCATION for a relaxing family trip to the Keys.

Topsider Birthday Stay

Topsider was a great little resort

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.

I have been visiting TOPSIDER annually for the last 10 years or more. It continues to be one of my favorite places. The staff takes excellent care of the property and the bungalows have everything you need. The beach is lovely & sunsets are amazing. 

This is not a luxury resort, for those looking for luxury. The inside of the condos are very basic but everything is new and top notch. They are well cleaned!! But not daily. You are in charge of your own mess once you arrive. Trash is picked up throughout the week. The internet is fast, there are many shared grills, kayaks & bikes available. They have a beautiful pool & hot tub. Each unit has its own washer & dryer as well as it’s own boat slip. 

Manny takes excellent care of everything & if you’re nice he’ll give you a homegrown papaya larger than any football. You’ll want to bring all groceries in. Publix on your way into Islamorada is the best bet. But there’s a gas station nearby if you’re in a pinch. 

Definitely stay here if you want a low key getaway. I’ve been here for weeks solo, romantic weekends, and with family. It’s our under the radar gem!

Our Family Secret!

Love this resort!  Been going to Topsider for over 40 years and it gets better every year.  Love the unit, the grounds, the beach and the pier!  Thanks to all the staff for their hard work, as it shows in the beauty of the property.  Thanks to all the families in week 22, it was great to see you all again!  And thanks to all the new folks, Welcome and come back to see us!

Topsider - Spectacular as usual

Three fishing buddies on vacation for all over the country. Found Topsider online by accident. This is a time-share facility that lists available units to fill cancellations. Communication with the office staff, before arrival and during our stay, was outstanding. The unit just happened to be right at the water edge. Outstanding view of the Gulf. The unit was clean and well appointed. The beds were very comfortable. The heated pool was immaculate. Ample parking, boat ramp, private pier and dock, private beach, washer-dryer in the unit. Very complete. All units are raised for flood surge protection. Stairs to access. May not be ADA accessible. Other than that we could not have had a better stay. Highly recommended.

Hidden gem

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.

Topsider Resort

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