
Beachfront holiday rentals in Islamorada
Find and book unique beachfront homes on Airbnb
Quick stats about beachfront rentals in Islamorada

Total holiday rentals
Explore 220 holiday rentals in Islamorada

Nightly prices starting at
Islamorada holiday rentals start at €77 per night before taxes and fees

Verified guest reviews
Over 1,730 verified reviews to help you choose

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

Pet-friendly holiday rentals
Find 150 rentals that welcome pets

Holiday rentals with a pool
210 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wifi availability
210 of Islamorada holiday rentals include wifi access

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

4.6 Average rating
Islamorada stays receive an average rating of 4.6 out of 5 from guests
Top-rated beachfront rentals in Islamorada
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

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.

Amazing Ocean Front Views Key Colony Beach
Everything is brand new in this gorgeous condo with amazing oceanfront views. #40 has two queen beds, well equipped kitchen with full-size appliances and everything you need to cook & serve meals. Fast, reliable WiFi, large SmartTV. Super cold new A/C unit Enjoy stunning views of sunrise from your private balcony & sunsets next door at Sunset Park. Heated pool, beach BBQs & tiki huts for guest use We are centrally located to awesome Keys adventures just a few miles drive from the condo.

🏝 Oceanfront Paradise Awaits You
Bring your boat to next vacation in tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise 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, restaurant, bar, marina with boat ramp and dockage, boat & trailer storage, and more - all situated on 60 lush tropical acres.

My Little Oasis2 Waterfront Retreat, Key Largo
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.

Tropical Getaway
This light, airy two bedroom condo is located in the community of Kawama. Overlooks a small lake, where people swim, kayak and paddleboard. The condo community features two pools, tennis courts, playground, fishing, beach and marina. A long jetty extends out in the ocean where you can watch the beautiful sunrises or sunsets in the afternoons. Centrally located in Key Largo near restaurants, shopping and attractions. Come down and enjoy the peaceful atmosphere of our tropical area.

Waterfront Villa & Sunset Views
Come and relax on your own veranda that overlooks the turquoise waters of the beautiful Duck Key. The outdoor living space is quiet and serene, making it a perfect place to unwind. Families and honeymooners alike can enjoy this island oasis. Centrally located at Mile Marker 61, Duck Key is just a short drive to Key West. Explore everything the Florida Keys have to offer or stay local to enjoy world-renowned restaurants, fishing, snorkeling, and diving. The opportunities are endless.

Vibrant Beachfront Villa
Welcome to Beachfront Villa that has recently been renovated. The 2 bedroom 1.5 bath luxury villa is located in the popular area of Duck key alongside of Hawks Cay Resort. Duck Key marina is located across the street where you can dock your boat or charter a boat for the day. Enjoy stunning sunset views from the back porch. Kitchen includes all amenities including silverware ,plates , cups , and pots. Linens and towels provided. *** Pets welcome with host approval and pet fee. ****

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.

Romantic Bayside Guesthouse peaceful 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. *Guesthouse on bayside not Bayfront ! Same property private from the residence! "No pets inside the Guesthouse "

Reel Large END Unit in Ocean Point Suites
Paradise awaits you in this large END unit, 2 BR/2BA in the highly desirable community of Ocean Pointe Suites! Newly renovated Modern Beach decor unit with breathtaking views from our Private beach and Marina are just a few highlights of this island retreat. Restaurant/Bar on site with beautiful views of the ocean. Live band and happy hour daily.
Popular amenities for beachfront rentals in Islamorada
Pet-friendly beachfront home rentals

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

Houseboat Getaway In Marathon

Relaxing Town home with great water views

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

New Private 4/3 Single Family - Kayaks & Bicycles+

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!

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

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

NEW! Casa Azul - Golf Cart, 2 King, Pool, Kayaks

Oceanfront Resort W/Indoor Pickleball - Speakeasy!

Beachside Unit 33-Private Tropical Beach Plus Pool

NEW luxury RV, Marina, 6 beds&1.5 baths, 2 pools!

Kawama Yacht Club and Molasses Reef Marine

Exceptional vaca in Angler's Reef Islamorada

Closest Oceanfront Home - 3 Stories, Views & Dock

P01 - New 3 bed, 3 bath with private pool
Private beachfront home rentals

Grouper Getaway @ Ocean Isles Fishing Village

Cabana Club Condo: Key Colony Beach, FL

*New* Turtles Pace-Private Beach

First Floor Coastal Escape | Restaurant Onsite

Treetops Apt.Sleep1-4 Beach Steps Away

Panoramic Ocean Views, Ocean Pointe Condo

Key Largo Tiny House, Marina, Beach + Pool Access

Private Beach in Marathons Key Colony Beach
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €293 | €331 | €383 | €313 | €269 | €276 | €331 | €316 | €312 | €269 | €254 | €286 |
| 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 |
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Biscayne National Park
- Calusa Campground
- Schnebly Redland's Winery & Brewery
- Homestead-Miami Speedway
- Coral Castle
- Bahia Honda State Park
- Seven Mile Bridge
- Robbies Marina Of Islamorada
- Everglades Alligator Farm
- Theater of the Sea
- Ernest F. Coe Visitor Center
- Key Largo Kampground And Marina
- Florida Keys Aquarium Encounters
- Harry Harris Beach and Park
- Dolphin Research Center
- Monkey Jungle
- Founder's Park
- History Of Diving Museum
- Homestead Bayfront Park
- Conch Key





