Bayside Villas by Islander Resort

Check-in at the hotel is at 4 p.m. Early check-in is possible for a fee of $100. 

Checkout at the hotel is at 11 a.m. Late checkout is possible for a fee of $100 until 1 p.m. Late checkout is based on availability        

The minimum age for check-in at the hotel is 21 years old.       

Yes, Bayside Villas offers exclusive packages and seasonal promotions throughout the year. Guests can enjoy savings on extended stays, Florida and Georgia resident rates, and other special offers available only when booking direct. Visit our Offers page to view current promotions.

Each Bayside Villa features two bedrooms and a pull-out sofa, accommodating up to six guests comfortably. Rates are based on the standard occupancy, and no additional guest fees apply up to the maximum occupancy limit.

You can modify or cancel your Bayside Villas reservation by clicking the “Manage My Booking” link in your confirmation email or by contacting our reservations team at 888.787.0084. Please note that cancellation policies vary by rate and offer, so be sure to review the terms associated with your booking.

Yes — Bayside Villas gift cards are available and can be purchased online or at the resort. They may be used toward accommodations, dining, and select Islander Resort experiences. To order, visit our Gift Card page or contact our team at (305) 664-2031.

Most reservations may be canceled by 4:00 PM local time at least 72 hours prior to arrival to avoid a cancellation fee equal to one night's room rate plus tax. If departing earlier than confirmed, the same notice is required. Select holiday and peak travel dates may have different cancellation terms, including December 26 through December 31, 2026.

Advance Purchase reservations are prepaid and non-refundable. Guests may request a one-time change of travel dates without penalty if requested at least 72 hours prior to arrival, subject to availability. Any difference in room rate for new dates will apply.

No. Cancellation terms may vary based on the rate plan, package, promotional offer, or stay dates selected. Guests should review the policy shown at the time of booking.

Islander Bayside Villas offers a collection of spacious two-bedroom, townhouse-style villas designed for families, groups, and extended stays in Islamorada. Guests can choose from several villa categories, including Bayfront Two-Bedroom Villas, Bay View Two-Bedroom Villas, Preferred Bayside Two-Bedroom Villas, and Bayside Two-Bedroom Villas, along with accessible villa options for guests who require additional accessibility features.
Each villa features a residence-style layout with two bedrooms, a full kitchen, a living area with a sofa bed, private outdoor space, and room for up to six guests, creating a comfortable home base for exploring the Florida Keys.

Cancellation policies at Bayside Villas in Islamorada may vary depending on the rate or promotion selected at the time of booking. Under the standard cancellation policy, reservations must be canceled by 4:00 PM local time, 72 hours prior to the scheduled arrival date to avoid a charge of one night’s room rate plus tax. The same notice is required for early departures.
Please note that exception dates may apply, including but not limited to December 26–31, 2026, when different cancellation terms may be in effect. Guests can review the exact policy in their confirmation email or modify a reservation through the “Manage My Booking” link provided at the time of booking.

Yes. A daily resort fee of $60 plus tax per villa, per night is added to your stay at Islander Bayside Villas.
The resort fee includes premium WiFi, self parking, two in room bottled waters, and pool access at Bayside Villas. Guests also enjoy full access to the amenities at Islander Resort, including the beach, beach chair and towel service, pools, dining, and recreational activities.
Additional benefits include one hour of daily use of bicycles, kayaks, and paddleboards for up to two guests at Islander Resort, pier fishing with fishing poles and bait, discounted admission to the Florida Keys History and Discovery Center, and local transportation within 1.5 miles based on availability.

Yes — the Bayside Villas pool is heated and available for guest use year-round. Pool hours are 8:00 a.m. to 10:00 p.m., allowing plenty of time to enjoy a relaxing swim or unwind by the water throughout the day.

Yes — Bayside Villas guests have full access to the Islander Resort’s fitness center. It is open 24 hours a day, 7 days a week and includes cardio machines, free weights, and strength-training equipment for your convenience anytime during your stay.

Yes — beach chairs and towels are available at Bayside Villas and at the Islander Resort beach and pool areas. Guests of Bayside enjoy full access to both locations, making it easy to relax by the bay or the ocean during their stay.

As a Bayside Villas guest, you have full access to all dining options at Islander Resort. On-site restaurants include Tides Beachside Bar & Grill, Drift, Coccoloba, and Sandy’s — each offering a distinct ambiance, local flavors, and flexible menus throughout the day.

Yes — each Bayside Villa features a full kitchen equipped with a refrigerator, microwave, stove, oven, dishwasher, and cookware, making it perfect for families and extended stays.

Yes. Every villa at Islander Bayside Villas includes a full kitchen, allowing guests to enjoy the comfort and convenience of home during their stay in Islamorada. Kitchens are equipped with appliances such as a refrigerator, microwave, stove, oven, dishwasher, and cookware, making it easy to prepare meals or snacks while traveling.

A stay at Islander Bayside Villas in Islamorada includes a variety of amenities designed to make your Florida Keys getaway comfortable and convenient. Guests enjoy premium Wi-Fi, complimentary self-parking, two in-room bottled waters, and access to the bayside pool. Boat slips are available for an additional fee.
Guests also have full access to the amenities at Islander Resort, including the beach, pools, dining, and recreational activities. At Islander Resort, guests can enjoy pier fishing with fishing poles and bait for catch-and-release, pool, beach chair, and towel service, and one hour of daily use of bicycles, kayaks, and paddleboards for up to two guests. Guests also receive discounted admission to the Florida Keys History & Discovery Center.

Yes. Islander Bayside Villas features a bayside outdoor pool available exclusively for villa guests. The pool area overlooks Florida Bay and provides a relaxing setting with lounge chairs and scenic water views.
Guests staying at Bayside Villas also enjoy access to the pools and beach amenities at Islander Resort, offering additional places to swim, relax, and enjoy the waterfront during their stay.

Islander Bayside Villas does not have dedicated on-site restaurants within the villas property. However, guests have full access to the dining venues at the nearby Islander Resort, which offers several on-property restaurants and bars.
Dining options at Islander Resort include Tides Beachside Bar & Grill, Drift, Coccoloba, and Sandy’s, offering everything from casual beachfront bites and tropical cocktails to elevated coastal cuisine.
These restaurants provide a variety of dining experiences throughout the day, making it easy for Bayside Villas guests to enjoy breakfast, lunch, dinner, or drinks during their stay in Islamorada.

No. Islander Bayside Villas does not offer self-service laundry facilities on the property. Each villa includes residence-style amenities such as a full kitchen, living area, and private outdoor space, but washers and dryers are not available in the villas.

Yes. Complimentary Wi-Fi is included with your stay at Islander Bayside Villas and is available throughout the property, including guest villas, pool areas, and common spaces.
Guests can also connect to Wi-Fi when visiting the nearby Islander Resort, making it easy to stay connected whether relaxing in your villa, by the pool, or while enjoying the resort’s dining and amenities.

Guests of Bayside Villas enjoy full access to Islander Resort’s beach and watersports activities, including kayaking and paddleboarding.

For even more adventure, explore guided excursions with our partners: Clearly Unique offers snorkeling, sunset cruises, and sandbar trips; EZ Goings provides guided private boat charters for tubing, wakeboarding, and family cruising; and Bamboo Charters delivers world-class fishing trips for everything from Tarpon and Snook to Grouper and Snapper. Learn more on our Experiences page.

Yes — Bayside Villas guests can book fishing charters and guided boat excursions directly through our partners. Bamboo Charters offers expert-led fishing trips for all experience levels, while EZ Goings provides guided private charters for sandbar outings, tubing, wakeboarding, and sunset cruises. Learn more or reserve your adventure on our Experiences page.

Families staying at Bayside Villas will find plenty to keep kids entertained. Young guests can enjoy swimming in the pools, playing on the beach, and joining in activities at the Islander Resort, including mini golf at the PuttTek course, ping pong, and cornhole. The resort also offers movie nights, beach games, and family-friendly events throughout the year, perfect for creating lasting memories together.

Bayside Villas guests enjoy easy access to the best of Islamorada and the Florida Keys. On property, explore the Florida Keys History & Discovery Center, located at Islander Resort.

Nearby favorites include the Theater of the Sea, Robbie’s Marina (famous for hand-feeding tarpon), and the History of Diving Museum. Guests can also stroll through local shops and galleries or attend the monthly Morada Way Art Walk, all just minutes from the villas.

Guests staying at Islander Bayside Villas can enjoy a variety of water activities on the bay and also access additional experiences at the nearby Islander Resort. Popular activities include kayaking and paddleboarding, allowing guests to explore the calm waters of Florida Bay and the surrounding mangroves.
Bayside Villas also offers boat slips (available for an additional fee) for guests bringing their own boat, along with easy access to boating and fishing opportunities in Islamorada, known as the Sportfishing Capital of the World.

When visiting Islander Resort, Bayside Villas guests can also enjoy additional waterfront recreation such as kayaks, paddleboards, bicycles, and pier fishing with fishing poles and bait for catch-and-release.

Together, these activities make it easy to enjoy both the relaxed bayside setting of the villas and the full range of oceanfront recreation available at Islander Resort during your stay in Islamorada.

Yes. Guests staying at Islander Bayside Villas enjoy full access to many of the amenities at the nearby Islander Resort. This includes the beach, pools, watersports, restaurants, and recreational activities available at the oceanside property.
Bayside Villas guests can also take advantage of activities and amenities such as kayaks, paddleboards, bicycles, pier fishing, beach chair and towel service, and dining venues including Tides Beachside Bar & Grill, Drift, Coccoloba, and Sandy’s when visiting Islander Resort.
This arrangement allows guests to enjoy the relaxed bayside setting of the villas along with the full resort experience offered at Islander Resort during their stay in Islamorada.

Yes. Islander Bayside Villas offers on-site boat slip rentals at the property’s bayside marina. The marina features 14 boat slips that can accommodate boats up to 24 feet in length, each with access to electricity and freshwater hookups.
Boat slips are available for an additional nightly fee and must be reserved in advance. This makes it easy for guests traveling with their own boat to explore Florida Bay and the surrounding waters of Islamorada during their stay.
Please note that there is no boat launch on the property, but nearby public launch sites in Islamorada provide convenient access for launching your vessel before docking at the villas.

Guests staying at Islander Bayside Villas can enjoy a variety of land-based activities during their stay. At the nearby Islander Resort, guests have access to recreational amenities such as pickleball courts, basketball, mini golf at the PuttTek course, ping pong, and lawn games.
Bayside Villas guests can also take advantage of bicycles available for exploring the surrounding area, as well as nearby attractions, shops, galleries, and restaurants throughout Islamorada. These activities make it easy to enjoy both relaxation and recreation while experiencing the Florida Keys.

Yes. Guests staying at Islander Bayside Villas receive one hour of complimentary daily use of bicycles, kayaks, and paddleboards for up to two guests at Islander Resort. These activities are available at the nearby oceanside property and are included as part of the resort amenities during your stay.

For your arrival, all Bayside Villas guests begin check-in at Islander Resort, located at 82100 Overseas Highway, Islamorada, FL 33036 (Oceanside, Mile Marker 82). Our team will walk you through the highlights of both properties, including amenities and experiences available during your stay.

Once check-in is complete, you’ll make your way to Bayside Villas at 81450 Overseas Highway (Bayside, Mile Marker 81.4), where our Bayside Hosts will be ready to welcome you. They’ll assist with unloading, help you get settled, and share tailored recommendations so you can ease right into the island rhythm.

Bayside Villas is a pet-friendly property, allowing guests to bring their pets along for a relaxing stay in Islamorada. A non-refundable pet fee applies per stay, and pets must be leashed in public areas. While pets are not permitted in pools or restaurants, they’re welcome to enjoy the open-air spaces and walking paths around the property. For complete details and guidelines, visit the Pet-Friendly page.

Bayside Villas are easily accessible from several major airports. Most guests fly into Miami International Airport (MIA) or Fort Lauderdale-Hollywood International Airport (FLL) and drive the scenic Overseas Highway (U.S. 1) to Islamorada — about 1.5 to 2 hours from Miami and 2 to 2.5 hours from Fort Lauderdale. The villas are also approximately 1.5 hours from Key West International Airport (EYW). Rental cars and private shuttle services are the most convenient ways to reach the property and explore the Keys.

The resort does not offer direct airport shuttle service; however, guests can easily arrange private transportation or shared shuttles through local providers serving Miami, Fort Lauderdale, and Key West airports. The Bayside Villas team is happy to provide recommendations or assist with scheduling transfers prior to your arrival.

Parking is complimentary — self-parking is included for Bayside Villas guests as part of your stay.

Bayside Villas and Islander Resort are cashless properties, and there is no ATM on-site. All major credit cards are accepted throughout the villas and resort.

Bayside Villas is a non-smoking property. Smoking and vaping are not permitted inside villas, on balconies, or in shared outdoor spaces. The only designated smoking area is located in the parking lot.

Yes — complimentary Wi-Fi is available throughout Bayside Villas and the Islander Resort property, including guest villas, pool areas, and common spaces.

Yes, children are welcome at Bayside Villas. Each spacious two-bedroom villa can accommodate up to six guests, making it ideal for families traveling together. With separate bedrooms, a living area, and a full kitchen, the villas provide plenty of space and convenience for a comfortable family stay in Islamorada.

While Bayside Villas does not host weddings or large events directly, guests have full access to the wedding and event venues at Islander Resort, located just across the street.

The resort offers a variety of stunning indoor and outdoor spaces — including Palm Terrace, Sunrise Pier, Islander Beach, Coral Pointe, Tropical Oasis, Great Lawn, Hibiscus Hall, and the Palmetto Room — ideal for ceremonies, receptions, meetings, and celebrations. Learn more on our Weddings page.

Yes — Bayside Villas guests are welcome to host private parties and gatherings at the Islander Resort’s restaurants or event venues.

Options include Tides Beachside Bar & Grill, Drift, Coccoloba, and Sandy’s, as well as a variety of indoor and outdoor event spaces. Our events team can assist with customized menus, décor, and setup. Learn more or inquire about availability on our Weddings & Events page.

Yes. ADA-accessible villas are available at Islander Bayside Villas. These villas are designed to provide a comfortable stay with features such as accessible entryways, wider pathways, and bathrooms with accessibility features. Guests who require an accessible villa should request this room type when making a reservation to confirm availability.

Islander Bayside Villas offers ADA-accessible villas designed to support guests with mobility or hearing accessibility needs. Accessible villas include features such as ramp entry, wider doorways, and bathrooms equipped with grab bars and an in-shower seat for added comfort and safety.
These villas also provide an open layout for easier movement, accessible bathrooms, and hearing-accessible features such as visual alarm systems, strobe lights, and a doorbell notification system.
Guests who require accessibility features are encouraged to request an ADA-accessible villa when making their reservation to confirm availability and ensure the accommodations meet their needs.

Yes. Islander Bayside Villas provides wheelchair-accessible routes to key public areas and amenities, including the pool area, parking areas, and pathways throughout the property. Accessible villas are also available to help ensure a comfortable stay for guests with mobility needs. Guests who require specific accessibility features are encouraged to note their needs when making a reservation.

Yes. All pools at Islander Resort are equipped with an ADA pool chair lift to assist guests with mobility needs.

The closest airports to Islander Bayside Villas in Islamorada are Miami International Airport (MIA) and Fort Lauderdale–Hollywood International Airport (FLL). From either airport, guests can enjoy a scenic drive along the Overseas Highway (U.S. 1) to reach the Florida Keys. The drive typically takes about 1.5–2 hours from Miami and 2–2.5 hours from Fort Lauderdale.
Another option is Key West International Airport (EYW), located approximately 1.5 hours south of Islamorada, which offers convenient domestic flights and connections from several major U.S. cities.

Islander Bayside Villas does not offer direct airport shuttle service. However, guests can arrange private transportation or shared shuttle services through local providers that operate between Islamorada and nearby airports, including Miami International Airport (MIA), Fort Lauderdale–Hollywood International Airport (FLL), and Key West International Airport (EYW).
Many guests also choose to rent a car, which allows them to enjoy the scenic drive along the Overseas Highway (U.S. 1) and explore the Florida Keys during their stay.

Yes. Bayside Villas guests can take advantage of a local shuttle service that operates within approximately 1.5 miles of the property, providing convenient transportation to nearby attractions and the Islander Resort. Guests may also choose to drive between the two properties to access the beach, pools, dining, and other resort amenities.

Guests staying at Islander Bayside Villas can easily access the amenities at Islander Resort by using the local shuttle service that operates within approximately 1.5 miles of the property, based on availability. Many guests also choose to drive between the two properties to enjoy the beach, pools, dining, watersports, and other resort experiences available at Islander Resort.