Topsider Resort
From
$203
/ night
Select dates to see prices and availability
From
$203
/ night
About this property
Enjoy a private beach, outdoor pool, and hot tub at this family-friendly condo in Islamorada.
Parking
Swimming pool
Non-Smoking Rooms
Tennis Courts
Safe-Deposit Box
Private beach
Location
75500 Overseas Highway, Matecumbe, Islamorada, Florida, United States of America
Room options
28
Apartment
Room details
1 Queen Bed
2 Twin Beds
1 Sofa Bed
Sleeps 6
800 ft²
Garden ViewPool ViewAir ConditioningHeatingKitchenPrivate PoolPrivate Entrance
Guest reviews of Topsider Resort
9.4
Superb
Based on 13 verified reviews
Facilities
7
Cleanliness
7
Rooms
7
Service
7
Location
7
Dining
7
Who stays here?
10
Rachel
Mar 13, 2026
·
Stayed 5 nights
Quiet, hidden gem in Islamorada—-the friendliest staff and guests. We love the beach, dock for night fishing, and kayaks. Will definitely be back!
Quiet, hidden gem in Islamorada—-the friendliest staff and guests. We love the beach, dock for night fishing, and kayaks. Will definitely be back!
10
sal
Sep 24, 2025
·
Stayed 4 nights
Unbelievable place with fish swimming near docs. Very comfortable places to stay and very friendly people all around.
Unbelievable place with fish swimming near docs. Very comfortable places to stay and very friendly people all around.
10
Thomas J.
Feb 21, 2025
·
Stayed 3 nights
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.
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.
8
Lupi
Jan 2, 2025
·
Stayed 3 nights
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!
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!
6
Danya
Feb 9, 2022
·
Stayed 3 nights
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.
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.
FAQs about Topsider Resort
Is parking available at the property?
Yes, the property offers free onsite parking for guests.
What are the check-in and check-out times?
Check-in is from 4:00 PM to 5:00 PM, and check-out is at 10:00 AM. Early or late check-in/check-out may be available upon request.
Where is the property located in relation to key landmarks?
The property is located on a private beach in Matecumbe, Islamorada, close to Indian Key Historic State Park and Windley Key Fossil Reef Geological State Park. It is a short drive to Anne's Beach and Robbie’s of Islamorada.
Does the property have a swimming pool?
Yes, the property features an outdoor heated pool, operational seasonally.
What are the policies for guests staying with children?
Children are welcome at the property. The minimum age for children to stay for free is not specified.
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