Best Vacation Homes in Islamorada
Fireplace/Heating
Pet Friendly
Kitchen
Parking
10.0
Spa
Pool
View
Breakfast
9.6- Pool
Ocean View
Balcony/Terrace- View
Oceanfront- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Oceanfront
Hot Tub- Fireplace/Heating
- Pool
Islamorada Luxury Rentals
1.0
Private Beach- Oceanfront
- Fireplace/Heating
- Pool
- Oceanfront
- Pool
- Ocean View
- View
Air Conditioner
Internet
Child Friendly
Bedding/Linens
10.0
Private Pool- Oceanfront
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
9.2- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
Islamorada Pet Friendly Vacation Rentals
10.0- Ocean View
- Balcony/Terrace
- View
- Pet Friendly
8.9- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
8.7- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
Islamorada Large Vacation Homes
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
9.5- Private Beach
- Oceanfront
- Pool
- Ocean View
9.6- Oceanfront
- Hot Tub
- Spa
- Fireplace/Heating
10.0- Pool
- Ocean View
- Balcony/Terrace
- View
8.0- Private Beach
- Oceanfront
- Fireplace/Heating
- Pool
10.0- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
10.0- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
Why Choose Rent By Owner for your Islamorada Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Islamorada Vacation Rentals
Where are the best neighborhoods to stay in Islamorada?
When exploring where to stay in Islamorada, Florida, you'll find a variety of neighborhoods that cater to different tastes and preferences. Each area offers unique access to the stunning waters and vibrant local culture, making it easy to find a convenient and comfortable place to call home during your visit. Whether you prefer the tranquil surroundings of quieter communities or the lively atmosphere of more central locations, the neighborhoods in Islamorada provide excellent options for enjoying this picturesque part of the Florida Keys. Booking your ideal vacation rental in these areas ensures a memorable stay in one of Florida's most captivating destinations.
Coral Cove
This area offers tranquil surroundings and easy access to pristine beaches, making it an ideal spot for relaxing beachfront stays. Here, you'll find vacation rentals that provide a peaceful retreat within the scenic beauty of the region.
View 643+ Rentals in Coral CoveLower Matecumbe Beach
Known for its stunning shoreline and laid-back atmosphere, this neighborhood is perfect for those seeking a serene escape by the water. The region offers a variety of vacation rentals that put you close to the beach and local outdoor activities.
View 334+ Rentals in Lower Matecumbe BeachWhite Marlin Beach
A popular destination for beach lovers, this community provides comfortable vacation rentals with direct access to beautiful sands and clear waters. It's an excellent choice for enjoying leisurely days in the sun and exploring the area's aquatic scenery.
View 344+ Rentals in White Marlin BeachVenetian Shores
Set along the waterfront, Venetian Shores boasts scenic views and easy access to boating opportunities, making it suitable for water enthusiasts. Here, your stay can be tailored to enjoy both relaxing leisure and adventurous pursuits on the water.
View 40+ Rentals in Venetian ShoresPlantation by the Sea
Offering lush landscapes and proximity to the coastline, this neighborhood provides a tranquil environment for seaside living. Vacation rentals here are perfect for guests looking for comfort and natural beauty during their visit.
View 736+ Rentals in Plantation by the SeaBonefish Bay
This peaceful bay area is renowned for its fishing and quiet ambiance, making it an appealing option for anglers and relaxation seekers alike. The available vacation rentals are ideally located to enjoy the area's aquatic adventures.
View 346+ Rentals in Bonefish BayPlantation Lake Estates
Surrounded by scenic lakes and lush greenery, this neighborhood is ideal for those who appreciate waterside views and outdoor recreation. Vacation rentals here offer a blend of comfort and serenity in a picturesque setting.
View 709+ Rentals in Plantation Lake EstatesSeabreeze Trailer Park
A casual community with a relaxed vibe, this area provides affordable options for travelers seeking a convenient and informal place to stay near the region's beaches and attractions. It’s perfect for an unpretentious getaway close to the water.
View 818+ Rentals in Seabreeze Trailer ParkBest Times to Visit Islamorada
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit this destination can enhance your experience, whether you're seeking warm weather for outdoor activities or a quieter atmosphere for relaxation in Islamorada’s exceptional vacation rentals.
Peak Season Highlights
Winter (December to February)
During these months, you can enjoy the warm climate and vibrant marine life, making it an ideal time for outdoor and water activities.
Spring Break (March to April)
This period tends to be lively with holidaymakers seeking pleasant weather and excellent fishing conditions in this destination.
Off-Season Highlights
Summer (June to August)
Although hotter and more humid, the summer months offer fewer crowds and great opportunities for snorkeling and relaxing on the beaches.
Fall (September to November)
As the region transitions into cooler weather, you'll find more affordable rates and a quieter atmosphere for exploring and enjoying local scenery.
Weekly Weather Forecast for Islamorada
How to Book Your Islamorada Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Islamorada
Common Vacation Rentals Amenities
What amenities can you expect?
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy access to private or shared outdoor pools for relaxing under the sun.
- Take advantage of waterfront views with direct access to the bay or ocean.
- Relax in your own outdoor seating area or patio designed for outdoor dining.
- Utilize outdoor grills or barbecue facilities to prepare fresh seafood and local cuisine.
- Make the most of fishing docks or piers available at many properties here.
- Benefit from lush landscaped gardens or tropical yards that enhance your outdoor experience.
- Explore nearby sandy beaches or tranquil boat slips for water-based activities.
Top Attractions Around Islamorada
What attractions are nearby?
Within this vibrant region, you can enjoy a variety of activities such as fishing, snorkeling, and exploring scenic waterways, all conveniently accessible from your stay here in Islamorada, Florida.
Family Activities
- Fishing Charters: Experience a family-friendly fishing adventure in the waters surrounding this destination, known for its abundant marine life and scenic ocean views.
- John Pennekamp Coral Reef State Park: Explore the underwater world with snorkeling or glass-bottom boat tours that showcase stunning coral reefs and vibrant aquatic life, perfect for all ages.
- History of Diving Museum: Discover fascinating exhibits on the evolution of diving technology, offering an educational and engaging experience for curious family members.
- Florida Keys Eco-Discovery Center: Learn about the region’s unique ecosystems through interactive exhibits and nature walks designed to inspire young explorers and nature lovers alike.
Adult Activities
- Deep-Sea Fishing Adventures: You can experience some of the best deep-sea fishing here, where you have opportunities to catch a variety of game fish in the abundant waters surrounding the area.
- Snorkeling and Diving Excursions: Explore vibrant coral reefs and underwater ecosystems that make this destination a premier spot for snorkeling and diving enthusiasts.
- Charter Boat Tours: Embark on scenic boat tours that showcase the region's stunning coastline, marine life, and unique natural beauty.
- Water Sports Activities: Take advantage of paddleboarding, kayaking, or jet skiing in the calm, clear waters perfect for adult adventure and relaxation.
Other Places to Stay in Islamorada, FL
Islamorada Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead for Water Activities: Schedule your fishing, snorkeling, or boating excursions early to secure the best spots and make the most of the area's renowned aquatic adventures.
- Explore Local Cuisine: Take time to savor fresh seafood at local eateries or enjoy beachfront dining that captures the true flavors of the region.
- Discover Hidden Gems: Wander beyond the popular spots to find secluded beaches and unique natural settings that offer a peaceful retreat in this destination.
- Respect the Environment: Practice eco-friendly habits, such as proper waste disposal and observing wildlife from a distance, to preserve the area's pristine beauty for future visits.
Transportation Options
- Rental Car Services: You can conveniently explore the area with rental car options, providing flexibility to visit nearby attractions and enjoy the scenic views at your own pace.
- Public Transportation: Buses and shuttles operate within the region, offering an affordable way to get around and reach popular destinations without the hassle of parking.
- Bike Rentals: For a more immersive experience, consider renting bikes to navigate the local waterways and charming streets of this tropical destination.
- Taxi and Ride-Sharing: Taxis and ride-sharing services are readily available, giving you quick and reliable transportation directly from your vacation rental here.
Local Customs Options
- Greeting with Respect: When visiting the area, you’ll notice locals often greet each other with a warm "Hello" or "Good morning," reflecting the region’s emphasis on hospitality rooted in Islamic tradition.
- Dress Modestly: Modest attire is appreciated here, especially during visits to local mosques or religious sites, fostering respect for cultural customs in this destination.
- Observance of Prayer Times: Many residents observe daily prayers at designated times, which is a common practice that influences the local rhythm of daily life in the region.
- Respect for Local Religious Events: During Islamic festivities or community gatherings, it’s customary to show respect and participate quietly, enhancing your experience of the area's cultural diversity.
Frequently Asked Questions About Islamorada?
1. What are the top vacation rentals in Islamorada?
There are a lot of options in Islamorada. If you plan on staying in the Islamorada area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Islamorada:
- ISLAMORADA PARADISE in ANGLERS REEF - Pool, Dock, Beach, Kayaks, Paddle Boards
- Islamorada home in Anglers Reef with Ocean Views, Dock, Com Pool & Private Beach
- The Caribbean Resort
- AQUAMARINE OCEANVIEW+”SPECIAL RATES”+nDOCK+POOL+GYM+SPA+”153”5 STAR REVIEWS!
- Beautiful Island Home in Anglers Reef! Ocean front community. Pool & boat slip.
- WATERFRONT FISHING COTTAGE/DOCKAGE + Walking distance to world famous Lorelei
- 5 bedroom - Deep Dockage & Heated Pool in Islamorada.
- Serenity by the Sea! Anglers Reef with Boat Slip Available!
- 4 Bedroom House in Angler's Reef, Includes 31' Boat Slip. Islamorada, FL
- Beautiful Islamorada Home In Angler's Reef. Amazing Views. Boatslip Included.
2. How many vacation rentals have private pools in Islamorada?
There are 251 vacation rentals with private pools near Islamorada. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Islamorada are best for families?
If you are looking for a family-friendly vacation home in Islamorada, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Islamorada:
4. How many Rentbyowner vacation rentals are available in Islamorada?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 1547 in the Islamorada area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Islamorada.
5. What is the cancellation policy for vacation rentals in Islamorada, Florida?
6. Are there any additional fees I should be aware of when booking a vacation rental in Islamorada?
7. How do I ensure my booking in this destination is secure and trustworthy?
8. What amenities are usually included with vacation rentals in the area?
9. Is there a minimum night stay requirement for vacation rentals here?
Islamorada Top Rated Vacation Rentals
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Private Pool
- Oceanfront
- Pool
- Ocean View
10.0- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
10.0- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
10.0- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
10.0- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
10.0- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
