
Beachfront holiday rentals in Islamorada
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Islamorada
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!
This hidden gem is anything but ordinary!!! Come enjoy a piece of paradise in Key Largo while you relax in this spacious NEW luxury RV. It has a BOAT RAMP, indoor/outdoor kitchen with a TV, outdoor speakers, 2 hammock chairs, outdoor sofa, outdoor dining, separate bedrooms including a bunk room that can sleep 5-6, 1.5 baths, 2 heated pools, 2 beaches, volleyball court, playground, & shuffleboard. There are so many outdoor activities to enjoy right at the Kampground, you'll never want to leave!

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.

Romantic cozy peaceful Guesthouse beach Sunsets.
Private Romantic Bayside Cabin/Guesthouse, peaceful settings, lovely sunsets, beach, fishing pier, lush gardens surrounded by nature and wildlife, birds, iguanas, manatees, dolphin’s, eagles, the beach is just a short walk away from the Guesthouse enjoying a cocktail, fishing, boats cruising by, kayaking, snorkeling or an amazing sunset. *This Guesthouse is on bayside not Bayfront ! Same property but private from the residence! "No pets, Airbnb-granted pets Exemption cus allergies reasons"

🏝 Oceanfront Paradise Awaits You
Bring your boat to next vacation in tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise Fl. Keys waters. Welcome to the most visited resort in the beautiful Florida Keys. Ocean Pointe is one of the most luxurious resorts in Tavernier, Florida Keys. The resort offers a private sandy beach, heated swimming pool, jacuzzi, tennis courts, oceanfront marina with boat ramp and dockage, boat & trailer storage, and more - all situated on 60 lush tropical acres.

NEW! CASA AZUL - Golf Cart, 2 Kings, 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, pools, one adult kayak, and three kids, kayaks, pickleball and tennis courts, and a unique swimming lagoon. Spend your days kayaking, fishing, boating, snorkeling, or visit the beach at John Pennekamp. Our villa has earned hundreds of 5-star reviews on all major platforms. No Hidden Fees!

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.

Turtle Nest 1 Private beach,Pool, 2bed 2bath
Ocean Pointe Suite is located on the Atlantic. Featuring ocean views from living room, master bedroom and balconies. King bed in master bedroom, Queen bed in guest bedroom, pull out queen sofa, 2 bathrooms, Smart TV's with cable WIFI. Completely stocked kitchen with all appliances. Amenities include heated swimming pool, private beach, marina with boat launch & dockage for extra fee book through marine info in pictures. Tennis courts, gazebo, located on 60 tropical acres.

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike
Enjoy a Key Largo adventure in our deluxe oceanfront condo WHICH INCLUDES 2 KAYAKS, 2 PADDLEBOARDS, 2 BIKES, TENNIS RACKETS/BALLS AND FISHING GEAR in a private beach resort community with a fishing jetty, a 24/7 boat ramp & a 3-acre salt-water lagoon for swimming, snorkeling, kayaking & paddleboarding. The condo sleeps 6 & is in the gated Kawama Community of Key Largo, surrounded by JOHN PENNEKAMP CORAL REEF STATE PARK. Marina boat slips may be available for rent.

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Ask for availability. 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 and NO pets.

Houseboat Getaway In Marathon
Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Exquisite Oceanfront Paradise - Key Colony Beach
Experience a wonderful ocean view from our beachfront condo in Key Colony Beach. Newly renovated studio condo in Key Colony Beach, Florida Keys. Unit #10 offers one king bed, a fully equipped kitchen with full-size appliances and essentials, reliable WiFi, and a SmartTV for a comfortable stay. Enjoy the heated pool and private sandy beach just steps away. Sunset Park is next door-perfect for catching a beautiful Florida Keys sunset.
Popular amenities for beachfront rentals in Islamorada
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Coco Plum Beach Paradise w Heated Pool & Boat Slip

2 BR/2 BA Oasis Kayaks, Pool, Beach & Dock Rental

Sale! Lux Home, Walk to Beach, 90' Dock, Pool

Relaxing Town home with great water views

Luxury Home at SeaGlass Cove by SoFLA Vacations

New Private 4/3 Single Family - Kayaks & Bicycles+
Beachfront home rentals with a pool

Seaside Villa~ Charming Beachfront Condo w/ Pool!

Deluxe Oceanfront 1/1 sleeps 4. Cafe & Pool Bar.

Grouper Getaway @ Ocean Isles Fishing Village

Private Beach in Marathons Key Colony Beach

Canal/Dock - Cabana Club - Pickleball - Remodeled

Paradise found! Sea-Esta Condo beach and pool.

2 Bdrm Oceanfront Complex Private Beach & Pool

Corner townhouse w/saltwater lagoon views
Private beachfront home rentals

BayFront Cottage,Bay Front Porch,Central AC,Beach

Charming Beach House directly ON the beach

Island Breeze

Sunny Beach Suite. 2 beds bath

Bayside Townhome in Islamorada with Boat Slip

Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool

Vibrant Beachfront Villa

Lazy Daze Beach House - Modern 5 Star Oceanfront
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $436 SGD | $493 SGD | $570 SGD | $400 SGD | $744 SGD | $400 SGD | $493 SGD | $470 SGD | $465 SGD | $400 SGD | $378 SGD | $426 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 beachfront rentals in Islamorada

Total holiday rentals
Explore 260 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 1,580 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 190 rentals that welcome pets

Holiday rentals with a pool
250 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wifi availability
260 of Islamorada holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Islamorada rentals
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
- Flat rentals Islamorada
- Bungalow rentals Islamorada
- Rentals with a firepit Islamorada
- House rentals Islamorada
- Rentals with a hot tub Islamorada
- Waterfront rentals Islamorada
- Family-friendly rentals Islamorada
- Rentals with beach access Islamorada
- Rentals with a fireplace Islamorada
- Beach house rentals Islamorada
- Resort rentals Islamorada
- Fitness-friendly rentals Islamorada
- Serviced apartment rentals Islamorada
- Rentals with a kayak Islamorada
- Rentals with a patio Islamorada
- Rentals with an EV charger Islamorada
- Townhouse rentals Islamorada
- Rentals with pools Islamorada
- Hotel rooms Islamorada
- Pet-friendly rentals Islamorada
- Rentals with breakfast Islamorada
- Villa rentals Islamorada
- Apartment rentals Islamorada
- Rentals with a washing machine and dryer Islamorada
- Beach apartment rentals Islamorada
- Rentals with outdoor seating Islamorada
- Luxury rentals Islamorada
- Beachfront rentals Monroe County
- Beachfront rentals Florida
- Beachfront rentals United States
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Long Beach
- Coral Castle
- Homestead-Miami Speedway
- Sea Oats Beach
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Theater of the Sea
- Everglades Alligator Farm
- Conch Key
- Calusa Campground
- Sunset Park
- Key Largo Kampground And Marina
- Seven Mile Bridge
- The Turtle Hospital
- Dolphin Research Center
- Florida Keys Aquarium Encounters
- Robbies Marina Of Islamorada
- Monkey Jungle
- Homestead Bayfront Park





