We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
You added Topsider Resort to your Saves list
75500 Overseas Hwy, Islamorada, FL 33036
Hotel amenities
Topsider Resort
We can't find prices for this accommodation
Our online travel partners don't provide prices for this accommodation, but we can search other options in Islamorada
Check In Check Out
Write a Review

33 reviews from our community

Traveler rating
See reviews for
Rating summary
  • Location
    4.5 of 5 stars
  • Sleep Quality
    3 of 5 stars
  • Rooms
    3 of 5 stars
  • Service
    3.5 of 5 stars
  • Value
    3.5 of 5 stars
  • Cleanliness
    3.5 of 5 stars
Traveler tips help you choose the right room.   Room tips (13)
Date | Rating
  • English first
  • German first
  • Any
English first
  • All months
  • Mar-May only
  • Jun-Aug only
  • Sep-Nov only
  • Dec-Feb only
All months
Chesapeake, Virginia
Top Contributor
52 reviews 52 reviews
6 hotel reviews
23 helpful votes 23 helpful votes
4 of 5 stars Reviewed 1 week ago

I purchased timeshare Week 7 in Unit 3C last year. This was our first visit to Topsider. This timeshare was bought sight unseen. It is the third unit from the waterfront. We had water and beach views from the windows in the living area and the deck. Week 7 this year happened to be one of the coldest in recent... More 

Was this review helpful? Yes
Cosby, Tennessee
17 reviews 17 reviews
6 helpful votes 6 helpful votes
5 of 5 stars Reviewed 2 weeks ago

On the Gulf side, just below the Indian Key bridges @ MM75.5 lies one the Keys' best vacation values. Each house is stand-alone, with dedicated dockage. Full kitchens, washer/dryer, 2 bdrm/2 bth,community pool & tennis, launch ramp and sand beach. Great area fishing, diving, restaurants and shops. No maid service, just peace and quiet in the glorious Keys!

Was this review helpful? Yes
Wyckoff, New Jersey
Top Contributor
81 reviews 81 reviews
15 hotel reviews
121 helpful votes 121 helpful votes
2 of 5 stars Reviewed 4 weeks ago

Based on the reviews I read on-line and the lack of pictures, I really wasn't expecting this timeshare exchange to be anything fancy. When we got there, we were more disappointed than anticipated. This is not a 'resort'. The place is an odd shape as you can see by looking at the website. If you are just simply looking for... More 

Was this review helpful? Yes 1
1 review
3 of 5 stars Reviewed January 4, 2015

Our first time down to the keys and we were so excited. We rented unit #15 which wasn't an ocean view but just a couple of steps to the little beach, dock and ocean. we got there right when the sun was setting and it was a beautiful location to see it. The grounds were kept well and the people... More 

Was this review helpful? Yes
Senior Reviewer
7 reviews 7 reviews
6 hotel reviews
22 helpful votes 22 helpful votes
3 of 5 stars Reviewed August 21, 2014

Topsider is well loved by the people that own units there and have been going there since childhood. It is definitely well worn and in need of an upgrade. The management and maintenance staff are super friendly and attentive. If you don't mind the accommodations, it has a pool, a beach area, and dock. Each unit has a combined kitchen... More 

Was this review helpful? Yes 1
Mt Shasta
Senior Reviewer
7 reviews 7 reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed March 8, 2014

I have been coming here for 26 years . This place is clean quite and unique. I would recommend it to anyone looking for an exceptional stay in the Key's! There is a pool, a hot tub , and a tennis court! Also , a private beach and a boat for docking !

Was this review helpful? Yes 1
Raleigh, North Carolina
Senior Contributor
34 reviews 34 reviews
6 hotel reviews
29 helpful votes 29 helpful votes
3 of 5 stars Reviewed February 23, 2014

This one'll take a while. When booking a unit here I asked the rental manager for a unit near the water. She said #3 was available so I booked. When I got confirmation in the mail the document said unit #16. I called to ask why the change to a unit so far from the water, she said the owner... More 

Was this review helpful? Yes 1
Mt Shasta
Senior Reviewer
7 reviews 7 reviews
4 helpful votes 4 helpful votes
5 of 5 stars Reviewed January 27, 2014

This resort is amazing . Ever since I was born my parents brought me on vacation to the Florida Keys . Every year it was Topsider!! I love the private beach, pool, and tennis court . There are also bicycles that you can ride for free and little boats you can paddle around in that are provided by the resort!... More 

Was this review helpful? Yes 2
Southend-on-Sea, United Kingdom
Top Contributor
60 reviews 60 reviews
5 hotel reviews
32 helpful votes 32 helpful votes
4 of 5 stars Reviewed November 21, 2013

It's too easy to pass Topsider Resort as you drive south on the Overseas Highway from Robbie's. The resort sign has seen better days and is situated well back from the road but don't let this put you off. If you persevere past the 'Private' signs you'll find yourself in a hidden paradise with tennis court, swimming pool, two small... More 

Was this review helpful? Yes 2
1 review
5 helpful votes 5 helpful votes
5 of 5 stars Reviewed July 25, 2013 via mobile

I can't believe some of these reviews by some people who seem to be high maintanence! This is the keys and you will find bugs! Tuesday and richard have been extremely nice since I have owned. 2001! Some people just can't take care of themselves on vaca. Love the place and would never trade. Manny is great and takes great... More 

Was this review helpful? Yes 5
Questions? Get answers from hotel staff and past guests. Ask a question
Owners: What's your side of the story?
Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.
Manage your listing

Been to Topsider Resort? Share your experiences!

Write a Review Add Photos & Videos

Additional Information about Topsider Resort

Address: 75500 Overseas Hwy, Islamorada, FL 33036
Location: United States > Florida > Florida Keys > Islamorada
Number of rooms: 20
Also Known As:
Topsider Hotel Islamorada

11 photos of this hotel

Traveler photos: See what travelers like you saw

All traveler photos (11)
Pool/beach area (2)
View from room (1)
Other (8)
Hotels you might also like...
Check In Check Out
Price Your Stay