Bayside Villas by Islander Resort

Islamorada beach hotel with 3 restaurants and outdoor pool

Choose dates to view prices

Where to?

Dates

November 2025

December 2025

Outdoor pool, pool umbrellas, sun loungers

Escape to Islander Bayside Villas and Boatslips, nestled in Matecumbe. Unwind by the pool or take advantage of fishing, sailing, and kayaking activities nearby. Connect with free in-room WiFi and enjoy bike rentals on site.

Excellent

Popular amenities

Bar
Pet friendly
Pool
Gym
Air conditioning
Free parking

Main amenities (10)

Daily housekeeping
Near the beach
3 restaurants and bar/lounge
Outdoor pool
Free area shuttle
Terrace
Picnic area
Barbecue grills
Limited hour front desk
Bike rental

For families (6)

Children stay free
Free cribs/infant beds
2 bedrooms
Kitchen
Second bathroom
Separate dining area

$302 total

includes taxes & fees

Nov 6 - Nov 7

Room options

Check availability for these dates

Tonight

Oct 31 - Nov 1

Tomorrow

Nov 1 - Nov 2

All rooms

3+ beds

Showing 5 of 5 rooms

2 bedrooms, premium bedding, pillowtop beds, in-room safe

Brand New Two King Bed Standard

Exceptional

Highlights

Furnished balcony

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchen

Full-sized refrigerator/freezer

Dining table

76 sq m
2 bedrooms
Sleeps 6
2 King Beds and 1 Double Sofa Bed

Brand New Two King Bed Preferred

Excellent

Highlights

Furnished balcony

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchen

Full-sized refrigerator/freezer

Dining table

82 sq m
2 bedrooms
Partial sea view
Sleeps 6
2 King Beds and 1 Double Sofa Bed

Brand New Queen/Queen Bedroom ADA

Good

Highlights

Furnished balcony

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchen

Full-sized refrigerator/freezer

Dining table

83 sq m
Sleeps 6
2 Queen Beds and 1 Double Sofa Bed

Brand New Two King Bay Front

Very good

Highlights

Furnished balcony

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchen

Full-sized refrigerator/freezer

Dining table

89 sq m
Bay view
Sleeps 6
2 King Beds and 1 Double Sofa Bed

Brand New Two King Bedroom Bay View

Exceptional

Highlights

Furnished balcony

Separate dining area

Separate sitting area

Air conditioning

Free cribs/infant beds

Kitchen

Full-sized refrigerator/freezer

Dining table

82 sq m
Bay view
Sleeps 6
2 King Beds and 1 Double Sofa Bed

Similar properties

Private beach, white sand, sun loungers, beach towels

Pool
Free breakfast
Pet friendly
Free WiFi

$194 total

includes taxes & fees

Nov 4 - Nov 5

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About the neighborhood

81450 Overseas Highway, Islamorada, FL, 33036

What's nearby

Florida Keys Brewing Co. - 8 min walk - 0.7 km
Islamorada Brewery & Distillery - 2 min drive - 2.4 km
Bud n' Mary's Dive Center - 5 min drive - 3.0 km
Theater of the Sea - 8 min drive - 7.3 km
Robbie’s of Islamorada - 10 min drive - 8.0 km

Getting around

Marathon, FL (MTH-Florida Keys Marathon) - 37 min drive
Miami Intl. Airport (MIA) - 95 min drive
Key West Intl. Airport (EYW) - 99 min drive
Miami, FL (MPB-Public Seaplane Base) - 100 min drive
Miami, FL (OPF-Opa Locka Executive) - 110 min drive
Free area shuttle

Restaurants

‪Lorelei Restaurant & Cabana Bar - ‬18 min walk
‪Wendy's - ‬2 min drive
‪Islamorada Fish Company - ‬4 min walk
‪The Trading Post - ‬11 min walk
‪The Square Grouper - ‬10 min walk

About this property

Bayside Villas by Islander Resort

Situated by the ocean, Bayside Villas by Islander Resort is a great choice for a stay in Islamorada. After splashing around at the outdoor pool, you can grab a bite to eat at one of the 3 restaurants or unwind with a drink at the bar/lounge.

At a glance

Hotel size

- 25 rooms
- Arranged over 2 floors

Arriving/Leaving

- Check-in start time: 4:00 PM; Check-in end time: anytime
- Minimum check-in age: 21
- Check-out time is 11 AM

Special check-in instructions

- The front desk is open daily from 9:00 AM - 7:00 PM
- Guests will receive an email within 24 hours before arrival with check-in instructions; front desk staffed during limited hours

Required at check-in

- Credit card required for incidental charges
- Government-issued photo ID may be required
- Minimum check-in age is 21
- Minimum Spring Break check-in age is 21

Children

- Up to 4 children (12 years old and younger) stay free when occupying the parent or guardian's room, using existing bedding

Pets

- Pets allowed (dogs only, 2 total)*
- Service animals welcome
- Specific rooms only, restrictions apply*
- Pets must be supervised

Internet

- Free WiFi in public areas
- Free WiFi in rooms

Parking

- Free onsite self parking
- Wheelchair-accessible parking and van parking on site

Offsite

- Free area shuttle within 1.5 miles

Other information

- Designated smoking areas

Property amenities

Food and drink

3 restaurants
Bar/lounge
Barbecue grills

Traveling with children

Children stay free (see details)
Free local shuttle

What to do

Sailing
Personal watercraft (motorized)
Beach nearby
Access to nearby outdoor pool
Free use of nearby fitness center
Bicycle rentals nearby
Ecotours nearby
Hiking/biking trails nearby
Scuba diving nearby
Scooter/moped rentals nearby

Services

Front desk (limited hours)
Bicycle rentals
Pool loungers
Pool umbrellas

Facilities

5 buildings/towers
Built in 2010
Picnic area
Terrace
An outdoor pool

Accessibility

Wheelchair accessible
Wheelchair-accessible parking
2 on-site accessible parking spaces
Assistive listening devices available
Wheelchair-accessible van parking
Wheelchair-accessible pool
Visual alarms in hallways
Well-lit path to entrance
Stair-free path to entrance

Room amenities

Be entertained

55-inch LCD TV
Cable TV channels
Streaming services

Home comfort

Air conditioning (climate-controlled)
Ceiling fan
Coffee/tea maker

Sleep well

2 bedrooms
Hypo-allergenic bedding
Blackout drapes/curtains
Queen sofa bed
Premium bedding
Pillowtop mattress
Free crib/infant bed

What to enjoy

Furnished balcony
Separate dining area
Separate sitting area

Freshen up

2 bathrooms
Bathtub or shower
Designer toiletries
Hair dryer
Towels
Toilet paper

Stay connected

Free WiFi
Free local calls

Food and drink

Full-sized refrigerator/freezer
Freezer
Microwave
Kitchen
Stovetop
Oven
Toaster
Free bottled water
Cookware, dishes, and utensils
Dishwasher
Blender
Ice maker
Dining table
Paper towels

More

Daily housekeeping
In-room safe
Cleaning supplies

Special features

Dining

Tides Beachside Bar - Onsite restaurant. Guests can enjoy drinks at the bar.

Coccoloba - Onsite restaurant. Open daily.

Drift On The Beach - Onsite restaurant. Open daily.

Sandy's Bar - Onsite bar. Open select days.

Fees & policies

Mandatory fees

You'll be asked to pay the following charges by the property at check-in or check-out. Fees may include applicable taxes:

Resort fee: USD 67.50 per accommodation, per night

Resort fee inclusions:

Additional inclusions
Beach access
Beach towels
Fitness/yoga classes
In-room bottled water
Partner property access
Partner property beach club access
Partner property pool access
Pool access
Sporting facilities or equipment

Pets

Service animals exempt from fees
Pet deposit: USD 200 per stay
Pets are allowed for an extra charge of USD 100 per accommodation, per night

Policies

This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room.

Only registered guests are allowed in the guestrooms.

This property does not have elevators.

Guests can rest easy knowing there's a carbon monoxide detector, a fire extinguisher, a smoke detector, and window guards on site.

This property accepts credit cards, debit cards and cash.

Credit cards accepted: Visa, Mastercard, American Express, Discover, Eurocard

This property is professionally cleaned.

Also known as

Bayside Islander

Islander Bayside

Islander Bayside Islamorada

Islander Bayside Resort Islamorada

Islander Resort Bayside

Bayside Townhomes Boatslips

Islander Bayside And Boatslips

Islander Bayside Villas Boatslips

Islander Bayside Villas and Boatslips Hotel

Islander Bayside Villas and Boatslips Islamorada

Islander Bayside Villas and Boatslips Hotel Islamorada

Frequently asked questions

Does Bayside Villas by Islander Resort offer free cancellation for a full refund?

Yes, Bayside Villas by Islander Resort does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.

Is there a pool at Bayside Villas by Islander Resort?

Yes, there's an outdoor pool.

Are pets allowed at Bayside Villas by Islander Resort?

Yes, dogs are welcome, with a limit of 2 total. There's a charge of USD 100 per accommodation, per night, and there's also a deposit of USD 200 per stay. Service animals are exempt from fees. Some restrictions may apply, so please contact the property for more details.

Is parking offered on site at Bayside Villas by Islander Resort?

Yes, there's free self parking.

What are the check-in and check-out times at Bayside Villas by Islander Resort?

Check-in start time: 4:00 PM; Check-in end time: anytime. Check-out time is 11 AM.

What is there to do at Bayside Villas by Islander Resort and nearby?

Have fun during the warmer months with activities such as sailing. Additional recreation nearby includes ecotours. Enjoy a swim in the outdoor pool or use the hotel's other amenities, which include a picnic area and access to a nearby outdoor pool.

Are there restaurants at or near Bayside Villas by Islander Resort?

Yes, there are 3 onsite restaurants.

Does Bayside Villas by Islander Resort have self-catered rooms fitted with kitchens or kitchenettes?

Yes, a kitchen is available in every room, and also includes a blender, a coffee maker, and a toaster.

Does Bayside Villas by Islander Resort have any outdoor private spaces?

Yes, every room features a furnished balcony.

What's the area around Bayside Villas by Islander Resort like?

Bayside Villas by Islander Resort is located on the waterfront in Matecumbe, a short 7-minute walk from Florida Keys Brewing Co. and 4 minutes' walk from Hurricane Monument.

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Bayside Villas by Islander Resort Reviews

8.8

Excellent

9.2/10

Cleanliness

9.0/10

Staff & service

8.2/10

Amenities

9.0/10

Property conditions & facilities

8.0/10

Eco-friendliness

Popular mentions

Location

Kitchen

Sunsets

Room

Family friendly

Service staff

Villa

Bathroom

Restaurant

Water

10/10 Exceptional

Jul 28, 2025

The property was beautiful, me and my family enjoyed our stay there. We would definitely stay there again. The pool, the rooms, and the veiws were just amazing. The beds were super comfortable and the veiw from the pool and rooms was amazing. Everything was super clean and neat when we got there. I would recommend to stay at this place if you go to the keys.

Lucia, 1-night trip

10/10 Exceptional

Jun 30, 2025

Excellent property. Clean, convenient and quiet.

R, 3-night trip

10/10 Exceptional

Aug 28, 2024

Wonderful easy to stay resort, just perfect!

Michelle, 1-night trip

8/10 Very good

Jul 20, 2025

Blessing in disguise

Property was smaller than what I was picturing with the photos but the villa was great wish the live ring rooms were bigger or maybe arranged differently, the beds were really comfortable and the whole property was quiet and relaxing it was also great that you could still enjoy everything at the main resort and preferred to stay at this location other than the main locstion

James, 5-night trip

6/10 Good

Mar 13, 2025

A little pricey for the overall villa because ours could’ve been a little cleaner but overall it was ok because the beds were very comfortable!

Carroll, 4-night trip

10/10 Exceptional

Aug 10, 2023

It is one of the best spots me and my family have stayed in in Islamorada!

Aileen, 1-night trip

10/10 Exceptional

Jul 14, 2024

Great quiet place

RANDELL RAMOS, 2-night trip

10/10 Exceptional

Oct 19, 2022

Will stay again!

Loved it, beautiful location, very laid back atmosphere, plenty of room.

2-night trip

10/10 Exceptional

Jun 7, 2024

Clean and close to everything

Ena, 7-night trip

8/10 Very good

Jan 20, 2023

Staying at the villas - while being able to enjoy the big resort, but having a break when needed.

Emily, 5-night trip

10/10 Exceptional

Mar 16, 2024

Did not know part of the awesome islander resort. Can sleep 5 easily. Great condition. Nice bayside pool.

Jay, 1-night trip

10/10 Exceptional

May 20, 2023

Excellent

Jose, 1-night trip

10/10 Exceptional

Aug 6, 2023

Everything is good. Except the pool needs to clean.

Luz, 1-night trip

8/10 Very good

Apr 17, 2024

The villas are lovely, comfortable beds, lots of room and the pool area is great plus access to amenities at the islander hotel is a great bonus, lovely pools and beach area/restaurants. My only negatives were we were in villa 102 and the road noise in the back bedroom was very loud, also the back bedroom needs curtains, it only had a Venetian blind and it was too light with the street lamps outside. Otherwise we loved this place and all the amazing staff who were so friendly.

Julia, 2-night trip

8/10 Very good

Feb 25, 2023

the location and units great, access to the amenities at there other location, the islander, was a plus kitchen could have used more, better items for cooking etc... and grill not working, no propane, promised it would be filled and didn't happen, important because many guest fish like we do and would like to cook there catch on the grill

Joyce, 5-night trip

2/10 Poor

Oct 31, 2024

I was unable to access the room. I booked after 7pm on Travelocity at the airport, drove over an hour from Miami and was told by security that he did not have a room key. No room available and I’m still waiting for a refund- terrible and fraudulent!!!!

Katherine, 2-night trip

8/10 Very good

Nov 28, 2022

Great friendly service. Clean units. Beautiful property. AC and humidity inside the unit is a problem. Had to keep AC very cold to hide moldy smell. Not very eco friendly as AC seemed to run 24/7. Also some carpenter ants found inside.

6/10 Good

Nov 16, 2022

Wifi bad, tv bad, stains all over carpeting and some mold on shower, pool unusable by 11am for rest of day

Darin, 6-night trip

10/10 Exceptional

Apr 22, 2024

Lovely sister property to the Islander - Resort; the, Islander Bayside resort Townhomes are wonderful. The Green Tuttle Inn. And the NEST across overseas highway great spirits & food. kitchens open until 10pm. 7 am green turtle breakfast. Or Mangrove Mike’s is a short walk North for breakfast. First night we walked to Lorelei, (15 minutes walk) for sunset. Best spot. This property is Slightly less than 2 miles NORTH from Bud and Mary’s marina and Lazy Days. Ideal for family or larger groups two king beds one shared bath upstairs, half bath downstairs full kitchen Living room. Staff were always upbeat and friendly; free shuttle via golf cart to the Islander main resort. Also booked snorkeling and sandbar tour with Clearly Unique water sports vendor at our Islander Bayside resort. Golf cart shuttle picked us up at Islander Bayside, and dropped us at Cheeca Lodge, where we embarked 3.5 hours - an hour snorkeling tour. Our captain Gunnar and first mate Brady, are professional, attentive, courteous, and marveled everyone with their knowledge of Different fish species we would encounter as we snorkeled. Next stop the ISLAMORADA Sandbar for Sunday Funday. Perfect. Chabby chic; centrally located. Great stay Islander Bayside Townhomes.

Keith, 4-night trip

8/10 Very good

Nov 12, 2022

Second time we stayed here. First times at the Villas. Two bedroom townhouse style with full kitchen and washer n dryer was great for a family of five. Great staff. Easy check in. Spent most of our pool time at the Islander. Everyone loved it. Our biggest issue was the key situation. Several times throughout the week all of keys would stop working. The Villas uses a different key system than the Islander. And there’s only someone in the Villas office during check in. We were part of a group of 18. And this caused a lot of issues. We had to wait up to and over an hour sometimes for someone to come over to make new keys. We heard their reason for keys not working so many times we could recite it ourselves. One of the villas had a 3 and 5 yr old that got locked in. Took an hour to get someone there. Almost called the fire department. They need to update their key system. Or keep someone at the desk at all times at the Villas. Everything else was great. We also used Clearly Unique for snorkeling and a Sandbar excursion. They run out of the Islander which was super convenient. The fun crew were also great. Ricardo was great! My kids had a great time hanging and playing soccer, basketball, ping pong and a bunch of other activities.

Paul, 5-night trip

10/10 Exceptional

Jul 29, 2025

The front desk manager was amazing. The units are brand new.

Placido, 2-night trip

2/10 Poor

Jul 22, 2025

Booked 2 places, got one. Lots of grief. Finally found other reservation, but interrupted sunset to figure it out & then had to move across the street. Didn’t get much downtime, etc, etc.

Denise, 1-night trip

8/10 Very good

Jul 18, 2025

The villas were nice and relaxing but the association with the islander resort made to stay great.

Troy, 4-night trip

8/10 Very good

Jul 18, 2025

My family and I have been traveling to this hotel for over 10 years. We have never arrived at the townhouse and found it to be dirty. The floor was covered in dust, with belongings from previous guests under the bed and sofa. A contact lens was on the dining room table and the cleaning staff who came to clean it removed it with the broom used to sweep the floor. They didn't clean the table afterward, at least with a cloth. The entrance hall had animal droppings on it and they only cleaned the small area where the droppings were.

Yadira, 6-night trip