
Holiday rentals with beach access in Islamorada
Find and book unique rentals with beach access on Airbnb
Quick stats about holiday rentals with beach access in Islamorada

Total holiday rentals
Explore 470 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 3,350 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 270 rentals that welcome pets

Holiday rentals with a pool
410 properties feature pools

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wifi availability
470 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
Top-rated rentals with beach access in Islamorada
Guests agree: these rentals with beach access are highly rated for location, cleanliness and more.

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!! 28 day rental. Enjoy sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Baycation Houseboat | Florida Keys 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 💫

Toes in the Sand - 2 Bedroom Condo Sleeps 4
Two bedrooms and two full bathrooms on the 4th floor with ocean views. Amenities include a huge heated pool and hot tub with a bar, a beach cafe serving food and drinks, a private Key's beach, viewing pier, rentable boat slips & boat trailer storage, tennis, pickleball courts, basketball, children's swings, and BBQ areas, and gated entry with 24-hour security! Just remember that you're on "Island Time," mon, relax and enjoy! Perfectly located between Key Largo and Islamorada, close to Penneka

Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

Escape to the Seaside - Tiburon Cottage
Our one bedroom suite features separate bedroom and living areas, giving you the space and comfort to relax, sleep and eat. Set yourself up in a large in-suite space with private entrance. The suite provides all the comforts of home. Unpack and stretch out in a stylish suite with a sofa, flat screen TV, complimentary Wi-Fi and premium cable programming or explore all the Keys have to offer. Here, you’ll have everything you need, because to us it’s not a temporary accommodation, it’s your home.

Best View Ocean Pointe Pool Beach King Bed, Gated
***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

Villa 5087 on Duck Key BOAT SLIP available
Enjoy a Fully Renovated Villa on Duck Key. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors, NO pets. Please do not take any items from the Villa. No pool access

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 Ocean Pointe
Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.

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!
Popular amenities for rentals with beach access in Islamorada
Apartment rentals with beach access

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

Beachside Unit 22 - Private Beach on Atlantic

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

Waterfront Escape | Pool, Tiki, Breakfast & Marina

Panoramic Ocean Views, Ocean Pointe Condo

Ocean Pointe | Pool, Hot Tub, View, Beach, Parking

Ocean Pointe 2309 with Ocean Views

Welcome to the Pelican Lodge !
House rentals with beach access

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

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

Lagoon View Retreat • 2 Kings• Pickleball• Marina

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

4BR 3B, Heated Pool & Spa, 60' Dock

Waterfront Key Largo Home - Tropical Paradise

Beach House, Private Pool, Dock, Gulf View Sunsets

Beachfront Villa - Florida Keys
Apartment rentals with beach access

Reel Large END Unit in Ocean Point Suites

Your Happy Place - Oceanfront

2BR - Key Largo Sunshine Getaway

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Key Largo Oceanside 3/3 Golf Cart & kayaks

Ocean views at “Sangria Sunrise” 10% off Charters

🏝 Oceanfront Paradise Awaits You
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $437 SGD | $497 SGD | $488 SGD | $450 SGD | $647 SGD | $418 SGD | $427 SGD | $428 SGD | $412 SGD | $396 SGD | $429 SGD | $450 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 |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Havana Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Kissimmee Holiday rentals
- Rentals with a washing machine and dryer Islamorada
- Rentals with a fireplace Islamorada
- Rentals with outdoor seating Islamorada
- Hotel rooms Islamorada
- Rentals with a kayak Islamorada
- Resort rentals Islamorada
- Beachfront rentals Islamorada
- Apartment rentals Islamorada
- Rentals with breakfast Islamorada
- Beach house rentals Islamorada
- Rentals with an EV charger Islamorada
- Rentals with a hot tub Islamorada
- Flat rentals Islamorada
- Rentals with a patio Islamorada
- Waterfront rentals Islamorada
- Fitness-friendly rentals Islamorada
- Serviced apartment rentals Islamorada
- Villa rentals Islamorada
- Family-friendly rentals Islamorada
- Rentals with pools Islamorada
- Bungalow rentals Islamorada
- Rentals with a firepit Islamorada
- House rentals Islamorada
- Luxury rentals Islamorada
- Townhouse rentals Islamorada
- Pet-friendly rentals Islamorada
- Beach apartment rentals Islamorada
- Rentals with beach access Monroe County
- Rentals with beach access Florida
- Rentals with beach access United States
- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Schnebly Redland's Winery & Brewery
- Coral Castle
- Homestead-Miami Speedway
- Calusa Campground
- Robbies Marina Of Islamorada
- Everglades Alligator Farm
- Seven Mile Bridge
- Theater of the Sea
- Bahia Honda State Park
- Ernest F. Coe Visitor Center
- Monkey Jungle
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Conch Key
- Key Largo Kampground And Marina
- Dolphin Research Center
- Founder's Park
- Harry Harris Beach and Park
- History Of Diving Museum





