Vacation rentals in Islamorada
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Islamorada
Guests agree: these stays are highly rated for location, cleanliness, and more.
Florida Keys Houseboat, unique waterfront stay-
Escape to the laid-back luxury of the Florida Keys aboard your own floating oasis. This fully equipped houseboat offers the perfect blend of comfort, adventure and true waterfront living. Wake up to breathtaking sunrises, sip your morning coffee as the marine life glide by, and fall asleep to the gentle sway of the water. Whether you’re celebrating something special or simply craving a one-of-a-kind getaway, this houseboat is the ideal home base for both keys adventures and peaceful retreats 💫
Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!
Waterfront Sunsets, Great Price, Relaxing Spot!!!
Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!
Flakey's
Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.
360 DEGREE WATERVIEW HOUSEBOAT
IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.
Blue Haven Key Largo | Ocean Pointe 1315
Tastefully decorated and newly renovated 2 Bedroom & 2 Bathroom Condo with a wonderful view of Florida Keys Nature. Relax and escape to this beautiful getaway in the heart of Tavernier, ideally located between Key Largo & Islamorada. The property itself has amenities galore: sparkling pool with hot tub and newly re opened POOL BAR, boat ramp and marina, tennis courts which convert into pickle ball courts, beach with pier, free parking and charcoal grills to cook your catch!
New Aqua Lodge 2Beds 1 Bath with Full Kitchens
This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!
Ocean views at “Sangria Sunrise” 10% off Charters
Welcome to Sangria Sunrise at Ocean Pointe Suites in the beautiful Tavernier Key Florida. Relax and enjoy all of the options offered such as Jr. Olympic sized pool, beach, marina, kayak rentals, tennis courts, and so much more! We invite you to come stay at this cozy and updated one bedroom and one bathroom top floor condo with the most amazing ocean views. We offer a very comfortable queen sized bed and also a queen sleeper sofa that's equally as comfortable.
2br/1ba w heated pool, 1 mile to robbies marina
Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!
Exquisite Oceanfront Paradise - Key Colony Beach
Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated ground floor with a stunning, clean white interior and just a few steps from our private beach and heated pool. Continental Inn Unit #10 offers one King size bed that sleeps two people. A fully equipped kitchen with essentials (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Reliable WiFi and Smart TV.
Cottage By The Sea
Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals
Villa in Paradise. Plunge pool. Middle of the Keys
Baja Breeze 🏝, a freshly updated, family-friendly, resort-style villa in the ♥ of the Keys. ♥ Please save Baja Breeze by clicking on the heart in the top right hand corner, this will help you find it again and share with others! 🛶 Waterfront canal view 🌴 Gated Resort Area 👙 Private spa pool 📍 Halfway between Key Largo and Key West ☀️ Outdoor dining/lounge area 🍳 Fully stocked Kitchen 📶 300Mbps+ Wifi
Popular amenities for Islamorada vacation rentals
Stay near Islamorada's top sights
Islamorada beach vacation rentals
LIC. MGR. - 2/2 VILLA - OCEANFRONT BEACH RESORT!
Charming Beach House directly ON the beach
Houseboat Getaway In Marathon
Renovated Anglers Reef 2BR + Sleeper + Ocean Views
NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!
Beachfront Villa - Florida Keys
Panoramic Ocean Views, Ocean Pointe Condo
Oceanfront 3‑Stories of Bliss • Dockage & Gameroom
Islamorada condo rentals
Gorgeous lagoon-front 2BR Townhouse with 2 pools
Your Happy Place - Oceanfront
Stylish & Secluded | Pool, Dock, Key Largo Living
Ocean Views at Ocean Pointe
Condo in Tavernier
Island Getaway at Ocean Point
Modern and Coastal Ocean Pointe 2307
Tequila Sunrise
Beach condo rentals in Islamorada
Villa 5027 on Duck Key BOAT SLIP available
Luxury Top Floor Suite W/ Unobstructed Ocean View
Deluxe Oceanfront 1/1 sleeps 4. Cafe & Pool Bar.
Reel Large END Unit in Ocean Point Suites
2BR - Key Largo Sunshine Getaway
Beach Heaven-Private Beach, Pool
Turtle Nest 1 Private beach,Pool, 2bed 2bath
Beachside Unit 33-Private Tropical Beach Plus Pool
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R5,291 ZAR | R6,105 ZAR | R6,235 ZAR | R5,340 ZAR | R6,300 ZAR | R5,258 ZAR | R5,405 ZAR | R5,291 ZAR | R4,998 ZAR | R4,868 ZAR | R4,965 ZAR | R5,584 ZAR |
| Avg. temp | 20°C | 22°C | 23°C | 25°C | 27°C | 28°C | 29°C | 29°C | 28°C | 27°C | 24°C | 22°C |
Frequently Asked Questions
What are the best places to stay in Islamorada?
Islamorada has a range of guesthouses, private rentals, and waterfront cottages, especially around the marina and near the coastline. Many visitors explore areas close to the water to enjoy snorkeling, local restaurants, and sunset views.
What are the best things to do in Islamorada with kids?
Families frequently enjoy exploring marine life exhibits, interactive aquariums, and sandy beaches. Guided snorkeling tours and paddleboard rentals are also popular ways for kids to discover sea creatures in shallow, clear waters.
What are some of the best things to do in Islamorada?
You can explore local museums, try sport fishing, and visit art galleries. Many visitors also join snorkeling or diving excursions to see vibrant reefs, or enjoy waterfront dining with fresh seafood.
How is the weather in Islamorada?
Islamorada has a tropical climate with winter temperatures around 61–78°F (16–26°C) and summers getting up to 91°F (33°C). Rain is more frequent in late spring and summer, so packing layers and sun protection is often recommended.
When is the best time to visit Islamorada?
Late winter through spring is often suggested for mild temperatures and lower rainfall, making it comfortable for beach activities and outdoor exploration. Summer brings warmer days and more rainfall, along with a vibrant fishing season.
What are the best places to visit in Islamorada?
Islamorada has museums focused on diving and local history, as well as marina areas with waterfront views. Explore artisan shops, marine life centers, and sculpture gardens for a taste of the area's culture.
What are some hiking trails in Islamorada?
You can walk shaded loops through tropical hammock preserves or follow nature trails in local parks. Paths wind past native plants, birdwatching spots, and occasional interpretive signs about the habitat.
What are some family activities we can do in Islamorada?
Families often explore touch tanks at marine centers, kayak calm waters, or join guided eco-tours. Beach picnics and shallow snorkeling are also frequently suggested for groups with children.
What are some of the best day trip ideas from Islamorada?
Many visitors plan outings to nearby state parks, animal sanctuaries, or botanical gardens. Guided boat tours, art village visits, and trips to other islands in the Keys are also frequently suggested.
Are there any pet friendly accommodations available in Islamorada?
Islamorada has pet-friendly rentals, including cottages and beachside homes. Some local parks and waterfront paths also welcome dogs on a leash, making it easier to enjoy the outdoors with your pet.
What are some local tips for visiting Islamorada?
Pack reef-safe sunscreen, as preservation of marine life is prioritized. Local eateries get busy at sunset, and water shoes can help when exploring rocky shorelines or tide pools.
What is Islamorada known for?
Islamorada is known for sport fishing, vibrant coral reefs, and a relaxed Florida Keys atmosphere. Visitors frequently highlight its clear waters, seafood cuisine, and picturesque sunsets.
What are the best hidden gems to explore in Islamorada?
Look for small artists’ studios, tucked-away hammocks with native flora, or local preserves not always on tourist maps. Independent galleries and small historic sites often give a different perspective on the area.
What are the best foods to try in Islamorada?
Islamorada is known for locally caught seafood like yellowtail snapper, stone crab, and Florida lobster. Key lime pie and conch fritters are frequently suggested treats, reflecting flavors of the region.
What should I bring for a trip to Islamorada?
Bring breathable clothing, swimwear, reef-safe sunscreen, and a sun hat for outdoor comfort. Water shoes and a reusable water bottle are helpful for exploring beaches and staying hydrated.
What is the nightlife in Islamorada like?
Nightlife in Islamorada is relaxed, with locally owned bars, seafood spots, and live music venues by the water. Evenings often feature acoustic performances, tropical cocktails, and sunset views.
What are the most popular events or festivals in Islamorada?
Islamorada hosts annual seafood festivals and sport fishing tournaments, with some events timed around winter and spring. Local art walks and culinary celebrations also draw visitors during peak travel periods.
Are there family friendly vacation rentals in Islamorada?
Family-friendly rentals are available throughout Islamorada, including waterfront homes and cottages with outdoor spaces. Many provide convenient access to beaches, playgrounds, and marine activities.
All about Islamorada
Islamorada’s beaches make for a great retreat, but the area is also known for its water sports. Whether you’re an angler looking to go tarpon fishing, an adventurer hoping to go dolphin spotting, or a boater who wants to cruise the backwaters before heading back to the Islamorada Marina’s protected dockage, there’s a getaway with your name on it. Known as the Village of Islands, Islamorada comprises five islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and Indian Key. Approximately halfway between Miami and Key West in the Florida Keys, it’s about 10 miles south of Tavernier, 16 miles south of Key Largo, and 81 miles north of Key West.
What are the top things to do in Islamorada?
Founders Park
This 45-acre park is the most popular of the village’s parks, especially because of its shallow beach on the bay side. In addition to tiki huts, picnic tables, volleyball courts, and a playground, there’s also an Olympic-size pool, walking trails, a driving range, and courts for basketball, tennis, and pickleball.
Windley Key Fossil Reef Geological State Park
Walk along the eight-foot-high walls of the former quarry, formed of Key Largo limestone (fossilized coral). The land was once owned by the Florida East Railroad, a company that helped build the Overseas Railroad in the early 20th century, connecting the mainland to Key West — but it was eventually damaged by hurricanes and shut down.
Alligator Reef Lighthouse
The namesake for the 136-foot-tall lighthouse, built in 1873, is not the reptile, but rather the USS Alligator, whose remains are deep underwater. Nowadays, the area is known for its reef with 500 sea life species, including barracudas and spiny lobsters.
Quick stats about vacation rentals in Islamorada
Total vacation rentals
Explore 800 vacation rentals in Islamorada
Nightly prices starting at
Islamorada vacation rentals start at R651 ZAR per night before taxes and fees
Verified guest reviews
Over 8,460 verified reviews to help you choose
Family-friendly vacation rentals
570 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 400 rentals that welcome pets
Vacation rentals with a pool
620 properties feature pools
Rentals with dedicated workspaces
460 properties have a dedicated workspace
Wi-Fi availability
790 of Islamorada vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Beachfront, and Gym across Islamorada rentals
4.7 Average rating
Islamorada stays receive an average rating of 4.7 out of 5 from guests
Destinations to explore
- Seminole Vacation rentals
- Central Florida Vacation rentals
- Miami Vacation rentals
- St Johns River Vacation rentals
- Orlando Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Four Corners Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Fitness-friendly rentals Islamorada
- Rentals with breakfast Islamorada
- Rentals with a kayak Islamorada
- House rentals Islamorada
- Rentals with a fire pit Islamorada
- Rentals with a fireplace Islamorada
- Apartment rentals Islamorada
- Rentals with beach access Islamorada
- Luxury rentals Islamorada
- Rentals with pools Islamorada
- Condo rentals Islamorada
- Family-friendly rentals Islamorada
- Beach house rentals Islamorada
- Rentals with a hot tub Islamorada
- Pet-friendly rentals Islamorada
- Rentals with a washer and dryer Islamorada
- Waterfront rentals Islamorada
- Villa rentals Islamorada
- Rentals with a patio Islamorada
- Beachfront rentals Islamorada
- Rentals with outdoor seating Islamorada
- Beach condo rentals Islamorada
- Townhouse rentals Islamorada
- Resort rentals Islamorada
- Rentals with an EV charger Islamorada
- Serviced apartment rentals Islamorada
- Hotel rooms Islamorada
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- The Turtle Hospital
- Coral Castle
- Calusa Beach & Loggerhead Beach
- History Of Diving Museum
- Sea Oats Beach
- Everglades Alligator Farm
- Conch Key
- Long Beach
- Theater of the Sea
- Monkey Jungle
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Sunset Park
- Florida Keys Aquarium Encounters
- Key Largo Kampground And Marina
- Seven Mile Bridge
- Calusa Campground
- Dolphin Research Center
- Robbies Marina Of Islamorada