
Waterfront holiday rentals in Islamorada
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Top-rated waterfront rentals in Islamorada
Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

Island Sanctuary Islamorada
Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

Paradise Casa Bayfront sunsets,pool,King bed ,dock
Welcome to Paradise Casa! Just five feet from the waterfront, you will think your on a cruise ship when you look out the windows. Breathtaking Unobstructed views of the sunset every night. This Glamping at its finest with an amazing pool. 2 bedrooms plus loft, with the main bedroom having a king size bed. Fireplace, fully stocked kitchen, massage chairs, 2 AC units for your comfort. 2 miles from John Pennekamp that has kayak rentals, glass bottom boats, create memories scuba diving/snorkeling

Sunrise Escape - Ocean Front Villa - Sleeps 10
Enjoy the sunrise while sitting on one of two terraces and sipping your morning coffee in the exclusive part of Kawama Yacht Club overlooking the Marina and Ocean. Enjoy the many choices for the day: Kayaking/paddle boarding just 20 steps from your door, walking to the south beach just 100 yards away, or walking to the beach jetty just across the marina. Or take a swim/snorkel in our swimmable lagoon or one of our two pools. Then bring a glass of wine to watch the breathtaking sunsets from our o

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 💫

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi
Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

Your Happy Place - Oceanfront
Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

Oasis2 in Key Largo With a million dollar view
Million Dollar view at a fraction of the price! This property is on the water with amazing bay views. It includes one kayak for 2 people, paddle board, fishing rod, washer and dryer, kitchen with all cooking utensils. Note: The upstairs room is not comfortable for seniors or adults, the ceiling height is 4 feet (an adult has to walk on his knees). The property is located on a residential island, restaurants, bars, stores and grocery stores are within a 15 minute drive from the property.

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.

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.

Turtles Nest 2 Beach, Pool, Restaurant 2bed 2bath
Turtle lovers rejoyce! Enjoy this Two Bedroom/Two Bath Condo with the perfect blend of style, comfort and convenience. Featuring a spacious living room and a fully stocked Kitchen. The Master bedroom features a King size bed and ensuite master bathroom. The guest bedroom features a Queen bed with a unattached bathroom. Both bathrooms feature a walk-in shower. The balcony offers views of the nature preserve and peek-a-boo views of the Atlantic Ocean!

Paradise in Key Colony Beach + Cabana Club
Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Waterfront Tiny House w Pool, Beach, and Boat Dock
Private community with 2 small beach areas, boat ramp, swimming pool, beach volleyball, children's area with playground, laundry facilities and more. Experience a tastefully decorated, modern 2-bedroom/1-bathroom waterfront tiny house. Relax outdoors with high-top bar seats, lounge chairs, and a grill, perfect for enjoying evenings under the twinkling patio lights.
Popular amenities for waterfront rentals in Islamorada
Waterfront apartment rentals

Ocean View Duplex Penthouse | Pool | Vista Two

Oceanfront Bliss • Wall-to-Wall Water Views + Pool

Ocean View 2br/2ba w/pool, bar, gym + dockage 28ft

Villa 4204 on Duck Key - Boat Slip available

Hidden Gem Islamorada | 1st Floor

Panoramic Ocean Views, Ocean Pointe Condo

Ocean Pointe Condo | Beach, Pool, Hot Tub & Tennis

4 Flr |2 Mastr |Oceanview |Jacuzzi |Beach |Marina
Waterfront house rentals

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks

Keys to Ohana. Ocean views. Private Pool, Hot Tub

Conch Cottage at Hawks Cay - Chic Tropical Retreat

Florida Keys Resort-Style Home w/ Pool & Dock 5/3

Large Waterfront Home, w/Efficiency, Pool, Kayaks

Beachfront Villa - Florida Keys

FL Keys Ocean Front Escape

Gorgeous Ocean View Home!
Waterfront apartment rentals

Beachside Unit 36 Private Patio & Beach Plus Pool

Reel Large END Unit in Ocean Point Suites

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Waterfront Apt Key Largo #4, 10% Off 7+, 5% Off 4+

Enjoy sunsets & sunrise in your home away home.

Ocean Views at Ocean Pointe

Modern and Coastal Ocean Pointe 2307

🏝 Oceanfront Paradise Awaits You
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $445 SGD | $496 SGD | $504 SGD | $420 SGD | $577 SGD | $410 SGD | $425 SGD | $384 SGD | $384 SGD | $361 SGD | $402 SGD | $463 SGD |
| 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 |
Quick stats about waterfront rentals in Islamorada

Total holiday rentals
Explore 460 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $115 SGD per night before taxes and fees

Verified guest reviews
Over 3,720 verified reviews to help you choose

Family-friendly holiday rentals
320 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 280 rentals that welcome pets

Holiday rentals with a pool
370 properties feature pools

Rentals with dedicated workspaces
320 properties have a dedicated workspace

Wifi availability
450 of Islamorada holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islamorada rentals

4.7 Average rating
Islamorada stays receive an average rating of 4.7 out of 5 from guests
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- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Long Beach
- Coral Castle
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Sea Oats Beach
- Theater of the Sea
- Everglades Alligator Farm
- Homestead-Miami Speedway
- Conch Key
- Calusa Campground
- Seven Mile Bridge
- Key Largo Kampground And Marina
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- Sunset Park
- Dolphin Research Center
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- Robbies Marina Of Islamorada
- Founder's Park




