Entire condo

Topsider Resort

Beachfront, with outdoor pool

Choose dates to view prices

Where to?

Dates

July 2025

August 2025

Condo, Multiple Beds | View from property

Outdoor pool, a heated pool, pool umbrellas, sun loungers

Overview
Amenities
Policies
Location
Host

Excellent

Entire condo

2 bedroomsSleeps 6

Popular amenities

Pool
Hot Tub
Air conditioning
Washer
Barbecue grill
Kitchen

Explore the area

75500 Overseas Hwy, Islamorada, FL, 33036

Sunset Drive Beach
‪1 min drive‬
Anne's Beach
‪3 min drive‬
Robbie’s of Islamorada
‪3 min drive‬
Marathon, FL (MTH-Florida Keys Marathon)
‪39 min drive‬

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Room options

Condo, Multiple Beds

2 bedrooms
Sleeps 6

About the neighborhood

Islamorada

Located in Matecumbe within a mile (2 km) of Sunset Drive Beach, this condo is within a few miles (5 km) of Robbie’s of Islamorada. This 20-room, 3.5-star condo building welcomes guests with a private beach, a marina, and an outdoor pool.

View more Condo Rentals in Islamorada

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 - 2.7 miles
Bud n' Mary's Dive Center - 7 min drive - 5.8 miles
Fiesta Key - 9 min drive - 7.2 miles

Getting around

Miami Intl. Airport (MIA) - 118 min drive

Restaurants

‪Robbie's of Islamorada - ‬3 min drive
‪Lazy Days Restaurant - ‬6 min drive
‪Islamorada Fish Company - ‬8 min drive
‪Square Grouper - ‬7 min drive
‪Green Turtle Inn - ‬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

Beachfront, with outdoor pool

Guests of this condo have access to a private beach, a marina, and an outdoor pool. If you decide to drive, there's free parking. Other amenities at this beach condo building include a hot tub, an outdoor tennis court, and free use of bicycles.

The condo is soundproofed and features a kitchen and space to spread out with 2 bedrooms. Guests can enjoy a flat-screen TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and free local calls. Housekeeping is not available.

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.

Languages

English, Spanish

Similar properties

On private beach
Pool
Pet friendly
Restaurant

$253 nightly

Aug 10 - Aug 11

Total includes taxes and fees

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

Bathtub or shower
Private bathroom
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

Access methods

Staffed front desk

Pets

This property doesn't allow pets

Property payment types

Important information

Fees

You'll be asked to pay these charges at the property:

Deposit: USD 150.00 per accommodation, per stay

These are all of the 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

Check-in: 4:00 PM—-5 PM
Check-out: 10 AM
Minimum check-in age: 21

Driving? This property offers free parking.

We should mention

Details about charges, deposits, or other important information:

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
This property accepts credit cards.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.
The property is professionally cleaned.

Additional information about polices, regulations, and more:

Registered guests are the only ones allowed in guestrooms.
No cribs or infant beds are available.
No rollaway or extra beds are available.

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

What's there to see close to this condo?

This condo is situated in Matecumbe, close to Anne's Beach, Bud n' Mary's Dive Center, and Fiesta Key. You'll also find Sunset Drive Beach and Robbie’s of Islamorada within a short drive.

Will I be able to park at this condo?

Yes, self parking is offered for free at the condo.

Is this condo next to a casino?

No, this condo is not connected to a casino.

Will I find an indoor pool at this condo?

No, this condo doesn't have an indoor pool; however, there are an outdoor pool and a hot tub.

What amenities will couples enjoy at Topsider Resort?

This waterfront condo offers plenty of amenities for couples including a private beach, an outdoor pool, and a marina.

Does Topsider Resort have a hot tub?

Yes, this condo has a spa tub.

Does this condo offer breakfast?

No, this condo doesn't offer breakfast.

Will this condo allow pets to stay free of charge?

No, pets aren't allowed at this condo.

Are there connecting rooms at this condo?

No, there aren't connecting rooms at this condo.

How far is the airport from this condo?

The closest major airport to this condo is Marathon, FL (MTH-Florida Keys Marathon), which is 24 mi away (32 minutes by car).

Can I book a room with a balcony at Topsider Resort?

No, there aren't any condo units with balconies at Topsider Resort.

Topsider Resort Reviews

8.8

Excellent

9.0/10

Cleanliness

9.0/10

Staff & service

8.6/10

Amenities

8.6/10

Property conditions & facilities

9.0/10

Eco-friendliness

10/10 Excellent

Thomas J.

Traveled with family

Feb 21, 2025

Liked: Cleanliness, room comfort

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

8/10 Good

Lupi, Clancy

Traveled with family

Jan 2, 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!

Stayed 3 nights in Dec 2024

10/10 Excellent

Nicole

Dec 18, 2022

Liked: Cleanliness, room comfort

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

10/10 Excellent

CHRISTY

Traveled with family

Dec 12, 2022

Liked: Cleanliness, amenities, property conditions & facilities

Small resort and friendly beautiful views

Stayed 9 nights in Dec 2022

10/10 Excellent

Daniel A

Dec 8, 2022

Liked: Cleanliness, property conditions & facilities

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

6/10 Okay

Darlene, Mt Pleasant

Traveled with partner

Aug 23, 2022

Disliked: Amenities

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

10/10 Excellent

Elizabeth

Feb 17, 2022

Liked: Cleanliness

Stayed 3 nights in Feb 2022

6/10 Okay

Danya

Traveled with partner

Feb 9, 2022

Liked: Amenities, property conditions & facilities

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

10/10 Excellent

Taraja

Traveled with family and small children

Feb 8, 2022

Liked: Cleanliness, amenities, property conditions & facilities

Would definitely come back to stay.

Stayed 3 nights in Feb 2022

8/10 Good

jeannine o., Missoula, MT USA

Jan 28, 2022

Liked: Cleanliness

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

10/10 Excellent

Nathan

Traveled with family

Jan 23, 2022

Liked: Cleanliness, amenities, property conditions & facilities

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

Stayed 7 nights in Jan 2022

6/10 Okay

Alexandre, Coconut Grove

Traveled with family

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

Stayed 4 nights in Nov 2021

10/10 Excellent

Levona H.

Nov 23, 2021

Liked: Cleanliness

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

10/10 Excellent

Jon

Traveled with family

Aug 15, 2021

Liked: Cleanliness, room comfort

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

10/10 Excellent

Verified traveler

Traveled with family

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!

Stayed 5 nights in Aug 2021

10/10 Excellent

Verified traveler

Traveled with family

Aug 13, 2021

Liked: Cleanliness, amenities, property conditions & facilities

Definitely coming back with my family

Stayed 3 nights in Aug 2021

10/10 Excellent

Verified traveler

Traveled with family

Aug 1, 2021

Liked: Cleanliness, amenities, property conditions & facilities

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

10/10 Excellent

Louisa

Traveled with family

Jul 18, 2021

Liked: Cleanliness, room comfort

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

2/10 Terrible

Verified traveler

Traveled with family and small children

Jun 12, 2021

Liked: Cleanliness

Disliked: Amenities

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

4/10 Poor

Verified traveler

Traveled with family

Apr 5, 2021

Disliked: Cleanliness

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

8/10 Good

jasmine h., Indianapolis

Mar 30, 2021

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

2/10 Terrible

Brooke P.

Mar 30, 2021

Liked: Cleanliness

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

8/10 Good

Tina J., Marshfield, WI

Mar 21, 2021

Liked: Cleanliness

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