Book on our site
Up to 10% cheaper
than Booking.com
Check rooms and rates
From548US$ /night
Check-in
16Jan2026Select date
Check-out
17Jan2026Select date
Rooms and Guests2 Guests, 1 Room
Key details

About the Hotel

75500 Overseas Highway, Lower Matecumbe Beach, Florida, United States, 33036
-
Next to the bay
Very good
7.6
8.6
/10
4.1
/5

Location

Topsider Resort occupies a prime position along the shores of the Florida Straits, nestled between the Atlantic Ocean and the Gulf of Mexico. Situated in Islamorada, the resort boasts a private beach that captures sunlight daily for a relaxing retreat. Guests can also enjoy a 180-foot T-shaped fishing pier extending into the bay, offering access to local fishing opportunities.

Accommodations

Each unit at Topsider Resort is a spacious, octagon-shaped villa, promoting privacy and comfort. The two-bedroom villas include a fully-equipped kitchen, washer and dryer, and ample storage space. With room for up to six guests, accommodations feature a king bed, two twin beds, and a queen sleeper sofa.

Amenities

The resort provides a variety of amenities to cater to all guests' recreational interests. Enjoy a heated swimming pool, jacuzzi, tennis courts, shuffleboard, and access to bicycles and kayaks. The beach area features lounge chairs and umbrellas for relaxing under the sun.

Entertainment

With a focus on outdoor activities, Topsider Resort offers equipment for kayaking and biking, allowing guests to explore the scenic surroundings. Fishing enthusiasts can access the private pier for shore fishing, while complimentary kayaks are available for water exploration. Nearby, numerous diving, snorkeling, and fishing charter options enhance the outdoor experience.

Family-Friendly Features

The resort caters to families with spacious villas and numerous kid-friendly amenities. Children can engage with the on-site staff, who provide fishing gear and lend assistance for bike setups. Nearby attractions such as the Theater of the Sea and local watersports add additional family entertainment.

Highlights

Location: Situated in Islamorada, between Atlantic Ocean and Gulf of Mexico

Accommodations: Spacious octagon-shaped villas with laundry facilities

Amenities: Heated swimming pool, tennis courts, and private beach access

Entertainment: 180-foot fishing pier, complimentary kayaks available

Must-do experiences

  • Relish fresh stone crab at Morada Bay Beach Cafe for a local favorite.
  • Kayak through the mangroves at Florida Keys Kayak Tours for serenity.
  • Visit the Florida Keys History and Discovery Center for cultural insights.
  • Catch the sunset at Robbies of Islamorada while feeding tarpon.
  • Explore Islander Watersports for thrilling jet ski adventures.
View all

Select your room type

The hotel offers a variety of rooms including double rooms, family rooms, and suites with breakfast, free cancelations, and special deals
Apartment
2 persons
800 sq. feet 
2 Single beds
Shower
Private pool

Price and Room Availability Calendar

Check availability and prices for your dates now!

Facilities

The hotel offers amenities for your comfortable stay and unforgettable experiences

General

  • No smoking on site
  • Free Wi-Fi
  • Parking
  • Safe deposit box
  • No pets allowed
  • Security
  • Private beach
  • Smoke detectors
  • Fire extinguishers

Sports & Fitness

  • Snorkelling
  • Canoeing
  • Cycling
  • Tennis court
  • Fishing

Guest Parking

  • Dryer
  • Cookware/ Kitchen utensils

Dining

  • Picnic area/ Tables

Business

  • Fax/Photocopying

Children

  • Board games

Spa & Leisure

  • Heated swimming pool
  • Outdoor swimming pool
  • Beach access
  • Beach umbrellas
  • Sun loungers
  • Garden area
  • BBQ facilities
  • Jacuzzi
  • Pool with view

Room features

  • Air conditioning
  • Sitting area
  • Garden furniture
  • Tea and coffee facilities
  • Dining table

Bathroom

  • Washing machine
  • Free toiletries

Self-catering

  • Dryer
  • Cookware/ Kitchen utensils

Media

  • Flat-screen TV

Room decor

  • Parquet floor
Show more

Location

75500 Overseas Highway, Lower Matecumbe Beach, Florida, United States, 33036
Map view
75500 Overseas Highway, Lower Matecumbe Beach, Florida, United States, 33036
Nearby
Lower Matecumbe Key
200 ft
Explore Lower Matecumbe Beach
Explore the Area
Top Attractions
Activities
Dining
Entertainment
Indian Key Historic State Park
Indian Key Historic State Park
5-minute drive
Historic site of an abandoned settlement with trails, wildlife, and snorkeling options, perfect for outdoor enthusiasts.
San Pedro Underwater Archaeological Preserve State Park
San Pedro Underwater Archaeological Preserve State Park
3-minute drive
Underwater archaeological preserve with snorkeling access to shipwrecks, offering unique marine exploration experiences.
Anne's Beach
5-minute drive
Beautiful beach with calm waters, picnic areas, and boardwalks, ideal for families and relaxation in the sun.
Snorkeling Tours
5-minute drive
Guided snorkeling tours available around the Keys, offering sightings of vibrant marine life. Rentals are often included.
Kayaking at Lignumvitae Key
5-minute drive
Kayak rentals to explore mangroves and wildlife at Lignumvitae Key, perfect for both tranquility and adventure seekers.
Morada Bay Beach Cafe
10-minute drive
Casual beachside eatery offering fresh seafood and tropical drinks, known for its sunset views and laid-back atmosphere.
Hungry Tarpon
8-minute drive
Local favorite serving hearty comfort food in a fun, casual setting, famed for their fish sandwiches and friendly vibe.
The Ray
8-minute drive
Vibrant venue with live music, featuring weekly performances and great drinks, suitable for all ages and nightlife lovers.
Islamorada Art Walk
10-minute drive
Monthly art event showcasing local artists, live music, and food trucks, appealing to families and art enthusiasts alike.
Getting around
City Centre
Lower Matecumbe Beach15 min  ·  4000 ft
Bus
Bus stop15 min  ·  4000 ft
Want to see Exclusive Early Booking Rate?
Get exlusive rates right now!
Check Rates
Property information and rules
Check-in
from 16:00-17:00
Check-out
from 08:00-10:00
Guest Parking
Public parking is possible on site for free.
Internet
is available in public areas for free.
Children & extra beds
There are no extra beds provided in a room.  There are no cots provided in a room. 
Pets
Pets are not allowed.
Number of rooms:
20
Questions of the users
About Topsider Resort
Are there boat docks available for guests at Topsider Resort?
10 November 2024
Topsider Resort offers docks for guests to use, providing easy access for boating activities. For more details regarding the available docks and permitted boats, please reach out directly to the resort.
Is the private beach on-site or do guests need to travel to access it?
15 December 2024
The private beach is conveniently located on the property, allowing guests to enjoy the beautiful bay side without needing additional transportation.
Can visitors fish on the resort grounds?
5 January 2025
Yes, fishing is allowed on the property, and guests can enjoy fishing from the resort's dock.
Do all accommodations at Topsider Resort feature balconies?
20 January 2025
Each unit at Topsider Resort has its own private balcony, perfect for enjoying the scenic views and fresh air.
Is there an additional resort fee for guests during their stay?
25 February 2025
There is a resort fee of $3.00 USD per day. Kayaks and bicycles are available for rent, with a $20 deposit for kayaks that is returned upon their return.
Are there provisions for docking boats and launching them nearby?
10 March 2025
Boat slips are available for use by guests. A small ramp is also provided for easy launching, with boat sizes limited to no more than 9.14 meters.
What recreational activities are available at Topsider Resort?
2 April 2025
Topsider Resort offers a range of amenities including a heated swimming pool, Jacuzzi, tennis and shuffleboard courts, as well as complimentary bicycles and kayaks for guests to explore the area.
How spacious are the accommodations at Topsider Resort?
15 May 2025
All units are designed with ample square footage, featuring fully equipped kitchens, comfortable living spaces, and multiple bedrooms, making them ideal for families or groups.
Can guests enjoy water sports while staying at Topsider Resort?
1 June 2025
Absolutely! The resort offers easy access to a variety of water activities such as snorkeling, kayaking, and fishing from the private pier.
What kind of amenities and services can guests expect at Topsider Resort?
20 July 2025
Guests at Topsider Resort can enjoy amenities such as complimentary Wi-Fi, a private beach, an outdoor pool, a fishing pier, and various recreational facilities, ensuring a comfortable and enjoyable stay.
Check-in
16Jan2026Select date
Check-out
17Jan2026Select date
Rooms and Guests2 Guests, 1 Room

Want to save 15%?

Unlock mobile deal now
Book your stay with special mobile rate on and save up to 15%.
Topsider Resort Lower Matecumbe Beach Beach photo

Topsider Resort

7.6
Very good9 reviews
4000 ft from center
493 US$
548 US$
per night
Mobile-only price