Executive Bay Club vacation rentals

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Find out more about Executive Bay Club

Why visit Executive Bay Club

  • Stunning Beach Views: Executive Bay Club offers breathtaking views of the ocean, perfect for relaxation and scenic enjoyment.
  • Outdoor Adventures: Engage in a variety of water sports and outdoor activities, including boat rentals and exploring nearby parks.
  • Family-Friendly Atmosphere: The resort is ideal for families, providing a welcoming environment for guests of all ages.
  • Charming Neighborhoods: Explore the unique local neighborhoods, filled with shops, dining, and cultural experiences.
  • Diverse Accommodations: Choose from a range of vacation rentals, including cozy condos and luxurious villas, to suit your needs.

Popular types of accommodation around Executive Bay Club

Planning a getaway to Executive Bay Club? You're in for a treat. Discover the charm of Islamorada with a range of vacation rentals, including private homes, condos, and villas. Enjoy beach access and unwind in a comfortable setting that feels like home. Whether you're seeking a cozy vacation home or a luxurious villa, Executive Bay Club offers the perfect base for your adventure in the Florida Keys.

  • Houses: The top choice for travelers at Executive Bay Club, offering spacious and comfortable living for families or groups.
  • Condos: A popular option for vacationers, providing modern amenities and stunning views.
  • Villas: Luxurious accommodations that offer privacy and upscale features for an indulgent stay.
  • Apartments: Convenient and cozy spaces ideal for couples or solo travelers seeking a home away from home.
  • Caravan Parks: A unique experience for those who enjoy outdoor living with community facilities.**

Top attractions near Executive Bay Club

At Executive Bay Club in Islamorada, Florida, you'll find a variety of attractions and activities to explore, including marinas, urban parks, and national/state parks. Whether you're seeking outdoor adventures, cultural experiences, or simply relaxing by the sea, there’s something for everyone. Enjoy activities at the club, rent a boat to explore the waters, and immerse yourself in the beautiful surroundings for an unforgettable vacation.

  • Islamorada County Park: A family-friendly urban park featuring lush green spaces, picnic areas, and playgrounds. It's perfect for outdoor activities and enjoying the local vibe while being just 0.3 miles from Executive Bay Club.
  • Founders Park: This vibrant marina offers exciting outdoor adventures, including kayaking and beach access. Located only 0.2 miles away, it’s an ideal spot for water sports enthusiasts and beach lovers.
  • Windley Key Fossil Reef Geological State Park: A stunning national park showcasing unique geological formations and scenic nature trails. At 2 miles from the club, it’s perfect for outdoor exploration and appreciating Florida's natural beauty.

Things to do recommended for couples

Ready for a romantic getaway in Islamorada? Dive into adventure at the Florida Keys Dive Center, just 3 miles away, or explore the charming shops at Rain Barrel Village, a mere 0.5 miles from Executive Bay Club. Unforgettable moments await you.

Things to do recommended for families

Families staying at Executive Bay Club can have a splash-tastic time at Jacob's Aquatic Center, located 12 miles away. This fun-filled aquatic center offers family-friendly vibes and activities that everyone will enjoy, making it a perfect day out for the whole family.

Things to do recommended for groups

Groups visiting Executive Bay Club can enjoy a lively atmosphere at Jimmy Johnson's Big Chill, just 12 miles away. For a more relaxed experience, visit the Florida Keys Brewing Co. or Islamorada Brewery & Distillery, both offering unique brews and entertainment vibes within 6 and 5 miles, respectively.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation around Executive Bay Club

If you're traveling with a group, family, or pets, or if you're considering extended stays, be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Executive Bay Club with a group: Think about how many bedrooms you'll require, as well as features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and many more on Vrbo.
  • Traveling to Executive Bay Club with young kids: Traveling with little ones can be a bit tricky. It's important to prioritize their comfort and safety, along with finding suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to family-friendly activities.
  • Taking your pets with you to Executive Bay Club: For many families, a trip just isn't the same without their furry companion. If you can relate, take a look at Vrbo listings that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels comfortable and at home.
  • Planning for a long term stay visiting Executive Bay Club: If you're in search of vacation rentals offering discounts for stays of a month or more, you've come to the right spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Executive Bay Club

Your vacation at Executive Bay Club in Islamorada, Florida, promises a delightful blend of relaxation and adventure. Nestled in an excellent location, this family-friendly destination offers stunning beach views and a welcoming atmosphere. Explore the nearby charming neighborhoods, indulge in water sports, or unwind on the beautiful sandy shores. Whether you're seeking romance or a fun-filled getaway, Executive Bay Club is the perfect base for creating unforgettable memories in the Florida Keys.

  • Islamorada: Nestled in the Florida Keys, Islamorada is a picturesque city renowned for its stunning beaches and vibrant outdoor culture. As the location of Executive Bay Club, it offers a perfect base for families seeking adventure and relaxation. Visitors can enjoy a variety of activities, from water sports like snorkeling and fishing to exploring local shopping areas and dining options. Local landmarks such as the beautiful family beach and bustling tourist precinct make it an ideal spot for memorable experiences and leisure activities under the sun.
  • Tavernier: Located just 5 miles from Executive Bay Club, Tavernier is a charming city that invites travelers to experience the best of Florida’s outdoor adventures. Known for its family-friendly atmosphere, it features beautiful beaches and a range of recreational opportunities, including shopping and dining at local malls. Tavernier is an excellent destination for those looking to enjoy a mix of relaxation and adventure, with easy access to engaging activities that highlight the natural beauty of the Florida Keys.
  • Seabreeze Trailer Park: This quaint neighborhood is only 0.2 miles from Executive Bay Club, making it a convenient spot for visitors. Seabreeze Trailer Park offers a laid-back atmosphere with a focus on outdoor family fun. With nearby beaches and golf courses, it’s perfect for those looking to soak in the sun or enjoy a round of golf. The community’s proximity to essential shopping areas and attractions makes it easy to immerse yourself in the local flavor while enjoying the beachside lifestyle.

Best time to go to Executive Bay Club

If you're planning a trip to Executive Bay Club, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from January to March, while off-peak times, like September to November tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January70.0°F (21.1°C)No Rain (Dry)Mostly SunnyModerately HighSlightly Low
February71.8°F (22.1°C)No Rain (Dry)Mostly SunnyModerately HighAverage
March72.9°F (22.700000000000003°C)No Rain (Dry)Mostly SunnyModerately HighAverage
April76.6°F (24.8°C)No Rain (Dry)Mostly SunnyAverageAverage
May79.3°F (26.3°C)Light RainMostly SunnyAverageAverage
June82.4°F (28.0°C)Light RainMostly SunnyAverageSlightly High
July83.8°F (28.8°C)Light RainMostly SunnyAverageSlightly High
August84.4°F (29.1°C)Light RainMostly SunnyAverageAverage
September83.3°F (28.5°C)Light RainMostly SunnyModerately LowSlightly Low
October80.2°F (26.8°C)Light RainMostly SunnyModerately LowSlightly Low
November75.9°F (24.4°C)Light RainMostly SunnyModerately LowAverage
December72.9°F (22.700000000000003°C)No Rain (Dry)Mostly SunnyAverageSlightly High

Booking with Vrbo is simple

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Plus, extending your stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental. We're here to help you find the best options.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the total booking amount. It's truly beneficial to be the organizer. Become a part of our One Key rewards program to unlock exclusive savings for members and earn OneKeyCash on qualifying stays. Sign up today and begin reaping the rewards.

Vrbo Trips: Planning made easy

Vrbo's cutting-edge Trip Board offers you a convenient way to plan your travels. You can start new trips, pick up right where you left off, or easily view and organize your travel plans. Any properties you've saved or booked before can now be accessed under Potential, Upcoming, or Current Trips. To get started with Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What are the best vacation rentals near Executive Bay Club?
The best vacation rentals near Executive Bay Club are primarily located directly in Islamorada, offering convenient access to the water. You will find a great selection of properties here, with choices ranging from spacious private vacation homes ideal for larger groups to comfortable condos, many with direct access to bay views. For those seeking the best vacation rentals near Executive Bay Club, focusing on Islamorada itself provides the most convenient options.

Many of these properties offer desirable amenities such as a private deck or patio, a balcony for enjoying the coastal breeze, and access to a refreshing pool, so you can have a comfortable stay. These homes are ideal for families or groups looking for a relaxing Florida Keys getaway.
Are there any cheap vacation rentals near Executive Bay Club?
There are several affordable vacation rentals near Executive Bay Club, especially if you are flexible with location and travel dates. Budget-friendly stays are typically around $230 per night in areas like Islamorada. Some stays even offer good deals in January and November during the cooler months, making it a great option for guests looking to experience the area without overspending. These rentals often include amenities such as WiFi, toiletries, and self-parking, and can range from private vacation homes to apartments, providing a clean, comfortable base for your stay.

To get the best value, consider staying slightly outside major hubs. If you're willing to drive a bit further, renting around nearby areas can be an affordable option. With a little planning, it is absolutely possible to find a comfortable stay near Executive Bay Club while keeping costs down.
What are the best pet-friendly vacation rentals near Executive Bay Club?
There are over 100 pet-friendly vacation rentals available near Executive Bay Club, primarily in Islamorada. These properties, frequently private homes and apartments, offer guests and their pets comfortable stays with amenities designed for convenience. Many rentals feature private decks and easy outdoor access, ensuring pets have space to enjoy.

When searching for the best pet-friendly vacation rentals near Executive Bay Club, guests should always confirm specific house rules, including any size restrictions or additional fees.
What are the top vacation rentals with pools near Executive Bay Club?
There are nearly 300 vacation rentals near Executive Bay Club that include access to swimming pools, with options ranging from private backyard pools to shared community pools, and even indoor facilities. Properties are concentrated in the surrounding areas of Islamorada. Many of these homes, including private vacation homes and condos, come fully equipped with amenities such as full kitchens, Wi-Fi, and outdoor spaces, making them ideal for families or groups seeking a comfortable stay.

When selecting your rental, consider whether a private outdoor pool for exclusive use is preferred, or if a shared pool, which might offer additional features like sun loungers or exercise pools, better suits your needs. For stays during cooler periods, looking for heated or indoor pool options can enhance your experience.
What are the best family vacation rentals near Executive Bay Club?
There are over 249 family-friendly vacation rentals near Executive Bay Club, primarily private homes and apartments. These properties often feature multiple bedrooms and bathrooms, full kitchens for meal preparation, and washer/dryers for convenience. Many also offer outdoor play areas like yards or gardens, and some even include additional entertainment such as video games, books, or playgrounds.

When selecting a vacation rental for your family's stay, consider properties that provide separate spaces for adults and children to relax, and prioritize those with essential amenities like a well-equipped kitchen to make family meals easier. Staying close to Executive Bay Club means less time traveling and more time enjoying the area.
Are there any luxury vacation rentals near Executive Bay Club?
Near Executive Bay Club, there are several luxury vacation rentals that combine waterfront surroundings with modern comfort. These properties often feature amenities such as private heated pools, premium bedding, private chefs, and private beach access. Guests can also find properties with onsite tennis courts and golf.

These homes are ideal for families or larger groups, often including high-speed WiFi and other entertainment options. Many of these exceptional properties are managed by highly rated Vrbo hosts, ensuring a professional and premium experience.
How much is a vacation rental near Executive Bay Club?
Vacation rentals near Executive Bay Club offer a wide range of options to suit different budgets, making it easy for guests to enjoy a memorable stay. Budget-friendly properties typically start around $230 per night, providing an affordable option. Mid-range rentals, including private homes, are generally around $520 per night, offering more comfort and privacy. For those seeking a more luxurious experience, upscale options can cost $750 or more per night, especially during peak seasons.

Enter your destination, travel dates, and number of guests on search to see the best options. You can use filters to set a minimum and maximum nightly price range along with other preferences. Rates may vary based on the season and specific amenities, but with a little planning, guests can find a rental that perfectly balances convenience and value.
Where should I stay when visiting Executive Bay Club?
When planning your stay near Executive Bay Club, several areas offer appealing vacation rentals.

The Upper Matecumbe Key area, where Executive Bay Club is located, provides direct access to the club's amenities and the beautiful bayfront. Properties here often feature private docks and stunning water views, great for guests interested in boating and water activities.

Further north, near Tavernier, you'll find a selection of vacation rentals that offer a quieter residential feel. This area is convenient for accessing local shops and dining, and properties often boast spacious layouts and proximity to other natural attractions. Access to Executive Bay Club from Tavernier is a comfortable drive.

To the south, the Lower Matecumbe Key area offers secluded properties with a more tranquil ambiance. These rentals are ideal for those seeking privacy and a peaceful retreat, often with their own beach access or lush tropical gardens.
What is the cheapest month to stay near Executive Bay Club?
The cheapest time to find vacation rentals near Executive Bay Club is typically during the late Autumn (November) and early Winter (January), excluding any major holiday weeks. November is frequently the cheapest month, often providing better deals on homes and condos compared to peak season rates. Guests can often find lower rates during these months, along with greater availability.
Are there any lakefront vacation rentals near Executive Bay Club
Lakefront vacation rentals near Executive Bay Club offer a great mix of comfort, scenery, and outdoor adventure. Many are located along the waters of the Florida Keys. These properties are a short drive from Executive Bay Club, offering convenient access to water activities such as motorboating, swimming, fishing, paddleboating, and parasailing, or simply relaxing by the shore.

These homes often feature spacious decks, fire pits, hot tubs, and fully equipped kitchens, making them ideal for families or groups. Guests can enjoy water views, spot wildlife, and unwind in peaceful surroundings after exploring local attractions.
Are there any top beachfront vacation rentals near Executive Bay Club
Beachfront vacation rentals near Executive Bay Club offer direct access to the sand, with many properties providing ocean-view balconies. Locations along Overseas Highway in Islamorada offer proximity to lively dining and shopping, while other spots provide a quieter setting for relaxation.

Guests can often find properties equipped with beach chairs, umbrellas, and beach towels. Many units feature ocean-facing rooms and private balconies. For those seeking more space, multi-bedroom homes or apartments are available, some with private terraces.
Are there any monthly vacation rentals near Executive Bay Club?
Vrbo offers excellent options for monthly vacation rentals near Executive Bay Club, making it a great choice for those who want to combine work and adventure. Monthly rentals often feel like a true home away from home, with fully furnished properties equipped with essential amenities like high-speed Wi-Fi, full kitchens, and comfortable workspaces, perfect for remote work or a summer vacation with the family. With flexible monthly rental options, Vrbo is a convenient and comfortable choice for extended stays near Executive Bay Club.
Are there any last-minute vacation rentals near Executive Bay Club?
Vrbo makes it simple to find last-minute vacation rentals near Executive Bay Club that blend comfort, style, and great value. Vrbo offers plenty of options for guests ready to pack up and go. Families and groups will find these deals especially appealing. Many spacious homes, complete with full kitchens, private pools, and multiple bedrooms, often become available when hosts want to fill open dates on their calendars.

Finding these stays is easy. Just enter your destination and travel dates, then use Vrbo's "Last Minute" or "Discounts" filter to uncover the best offers. You'll see reduced rates in the listings. Vrbo's last-minute rentals are a smart way to save while you explore. Whether you're planning a quick trip or a weekend getaway with friends, your last-minute escape is waiting, you just have to decide where to go next.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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