
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!!!

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 💫

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

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

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.

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.

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.

NEW! CASA PALMA - Golf Cart, 2 King-Size Beds, Pool, Kayaks
NO RESORT, GUEST OR MANAGEMENT FEES WHEN BOOKING MY HOMES! Welcome to your Key Largo vacation rental. This oceanside villa is family friendly and filled with amenities, including a private golf cart, one adult kayak and three kids kayaks, pickleball and tennis courts, multiple pools, and a unique swimming lagoon. Spend your days kayaking, fishing, boating, snorkeling, or the beach John Pennekamp. Our villa has earned hundreds of 5-star reviews on all major platforms. No hidden fees!

6. Waterfront Key Largo Studio, Near Kayaks & Reef
Unwind in this Modern Key Largo waterfront studio, nestled on a canal with ocean access near Rodriguez Key, Mosquito Bank, and shipwrecks. Just minutes from John Pennekamp Park. Enjoy a full kitchen, ice-cold A/C, Smart TV, Wi-Fi, and assigned parking. Boaters can reserve our dock or use nearby Pilot House Marina. Snorkel reefs, kayak mangroves, or dine at local favorites like The Fish House, Sundowners, and Key Largo Fisheries. Comfort, adventure, and location in one perfect stay.

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.

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

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

New Coastal Escape 2BR/2BA Oceanfront Condo

Beachside Unit 22 - Private Beach on Atlantic

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

New Waterfront Views | Pool & Tiki Bar

When Paradise is Key: Tropical Oceanfront Condo

Panoramic Ocean Views, Ocean Pointe Condo

Ocean Pointe | Pool, Hot Tub, View, Beach, Parking
House rentals with beach access

Heated&Cooled PrivatePool/CabanaClub/Bikes/PaddleB

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

Oceanfront mermaid house pool and dock

Waterfront Key Largo Home - Tropical Paradise

Escape to the Seaside!

Viamarhe House-Private beach, Kayak, yard games

Waterfront Paradise Key Largo. Casa Luna

Private Pool! Luxury Paradise Pointe, Pet Friendly
Apartment rentals with beach access

Sea Side Whimsy Ocean Pointe -06

Villa 5087 on Duck Key BOAT SLIP available

Reel Large END Unit in Ocean Point Suites

2BR - Key Largo Sunshine Getaway

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Key Largo Oceanside 3/3 Golf Cart & kayaks

Ocean Views at Ocean Pointe

Condo in Tavernier
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $415 SGD | $494 SGD | $491 SGD | $447 SGD | $643 SGD | $415 SGD | $424 SGD | $425 SGD | $410 SGD | $393 SGD | $426 SGD | $447 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
- Kissimmee Holiday rentals
- Four Corners Holiday rentals
- Villa rentals Islamorada
- Flat rentals Islamorada
- Rentals with pools Islamorada
- Rentals with a patio Islamorada
- Bungalow rentals Islamorada
- Apartment rentals Islamorada
- Family-friendly rentals Islamorada
- Rentals with breakfast Islamorada
- Rentals with a washing machine and dryer Islamorada
- Townhouse rentals Islamorada
- Rentals with a fireplace Islamorada
- Luxury rentals Islamorada
- Hotel rooms Islamorada
- Rentals with a firepit Islamorada
- Rentals with a kayak Islamorada
- Pet-friendly rentals Islamorada
- House rentals Islamorada
- Rentals with an EV charger Islamorada
- Beach house rentals Islamorada
- Serviced apartment rentals Islamorada
- Beach apartment rentals Islamorada
- Beachfront rentals Islamorada
- Resort rentals Islamorada
- Rentals with a hot tub Islamorada
- Fitness-friendly rentals Islamorada
- Waterfront rentals Islamorada
- Rentals with outdoor seating Islamorada
- Rentals with beach access Monroe County
- Rentals with beach access Florida
- Rentals with beach access United States
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Long Beach
- Coral Castle
- Sea Oats Beach
- Homestead-Miami Speedway
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Theater of the Sea
- Everglades Alligator Farm
- Conch Key
- Calusa Campground
- Key Largo Kampground And Marina
- Sunset Park
- Seven Mile Bridge
- Monkey Jungle
- Dolphin Research Center
- Robbies Marina Of Islamorada
- Florida Keys Aquarium Encounters
- Founder's Park
- The Turtle Hospital




