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

Villa 5027 on Duck Key BOAT SLIP available
Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. 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.

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.

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.

Beachside Unit 22 - Private Beach on Atlantic
Unit 22 Details: Main Floor, Walk-in Shower, 2 Queen Beds and Queen Sofa Pull-out, Maximum Occupancy 4 Guests, Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

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.

Luxury Top Floor Suite W/ Unobstructed Ocean View
Our spacious, 2 bedroom, well-appointed condo provides the perfect home away from home. Step onto your private balcony and soak in the mesmerizing views of the azure ocean and lush mangrove gardens. Escape to a tropical paradise and experience the ultimate keys retreat! Nestled in Tavernier, this property offers a perfect blend of comfort and breathtaking natural beauty. Indulge in the array of fantastic amenities available to our guests.
Popular amenities for Islamorada beachfront rentals
Pet-friendly beachfront home rentals

Beach Home and Boater’s Paradise Sombrero

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

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

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

Relaxing Town home with great water views

Vibrant Beachfront Villa

Boaters delight! 1 min to open water, Dock & Beach
Beachfront home rentals with a pool

Bayside Townhome in Islamorada with Boat Slip

Private Beach in Marathons Key Colony Beach

Canal/Dock - Cabana Club - Pickleball - Remodeled

Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool

Beach Breeze

Welcome to Paradise

2 Bdrm Oceanfront Complex Private Beach & Pool

Corner townhouse w/saltwater lagoon views
Private beachfront home rentals

Peaceful Island Getaway in Islamorada! Parking!

BayFront Cottage,Bay Front Porch,Central AC,Beach

Keys Cottage with Sleeping Loft Sleeps 6

Sunny Beach Suite. 2 beds bath

AMAZING VIEWS FROM THIS OCEANFRONT FLA.KEYS CONDO

SeaEsta! Bring your boat & 1 block to the beach!

Oceanfront community 114 Anglers Reef Islamorada

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 | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $561 NZD | $687 NZD | $659 NZD | $547 NZD | $1,018 NZD | $547 NZD | $674 NZD | $643 NZD | $636 NZD | $742 NZD | $545 NZD | $558 NZD |
| 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 250 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at $157 NZD per night before taxes and fees

Verified guest reviews
Over 1,620 verified reviews to help you choose

Family-friendly holiday rentals
130 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 180 rentals that welcome pets

Holiday rentals with a pool
230 properties feature pools

Rentals with dedicated workspaces
220 properties have a dedicated workspace

Wi-Fi availability
240 of Islamorada holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Islamorada rentals

4.5 Average rating
Islamorada stays receive an average rating of 4.5 out of 5 from guests
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- Beachfront rentals Monroe County
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Calusa Campground
- Biscayne National Park
- Florida Keys Aquarium Encounters
- The Turtle Hospital
- Coral Castle
- Calusa Beach & Loggerhead Beach
- Sea Oats Beach
- History Of Diving Museum
- Everglades Alligator Farm
- Conch Key
- Monkey Jungle
- Long Beach
- Theater of the Sea
- Schnebly Redland's Winery & Brewery
- Bahia Honda State Park
- Key Largo Kampground And Marina
- Homestead-Miami Speedway
- Seven Mile Bridge
- Curry Hammock State Park
- Dolphin Research Center




