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

Total vacation rentals
Explore 220 vacation rentals in Islamorada

Nightly prices starting at
Islamorada vacation rentals start at $127 CAD per night before taxes and fees

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

Family-friendly vacation rentals
100 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 150 rentals that welcome pets

Vacation rentals with a pool
210 properties feature pools

Rentals with dedicated workspaces
180 properties have a dedicated workspace

Wifi availability
210 of Islamorada vacation 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.

NEW! NO Traveler FEES! - Golf Cart, 2 King, Kayaks
No Hidden Fees! Book with confidence. No added Airbnb, resort, guest, or management fee when booking any of my homes. Casa Azul - Where the Salt Life Meets Luxury Welcome to your Key Largo vacation rental. No animals permitted, including service animals, due to owner allergies. This villa includes a private golf cart, pools, one adult kayak, three kids' kayaks, pickleball, tennis courts, a swimming lagoon, and a beach area. Enjoy kayaking, fishing, and snorkeling. Hundreds of 5-star reviews!

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.

🏝 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.

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 Resort W/Indoor Pickleball - Speakeasy!
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Key Largo's most upscale oceanfront community. The area has the distinction of being Key Largo's newest oceanfront gated destination, with some of the most unique amenities in all of the keys. It caters to those who simple desire the very best in luxury accommodations. Unique amenities include a Speakeasy Themed Rec. Area.

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 "

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.

Oceanfront Sunrise Condo Private Beach Heated Pool
Impeccable condo with some of the best direct ocean views in the Keys. Well equipped kitchen with full size appliances is stocked with everything you need to cook and serve meals. Enjoy stunning views of sunrise from our private beach and sunsets next door at Sunset Park. Heated pool, beach BBQs and tiki huts for guest use. We are centrally located to awesome Keys adventures just a few miles drive from the condo.
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

Coco Plum Beach Paradise w Heated Pool & Boat Slip

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

Relaxing Town home with great water views

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

SeaEsta! Bring your boat & 1 block to the beach!
Beachfront home rentals with a pool

2BR - Key Largo Sunshine Getaway

Lagoona-Matata

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

P87 - Modern 4 bedroom, 4 bath home on open water

Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool

Beachside Unit 33-Private Tropical Beach Plus Pool

*NEW* Private Beach, pool & fully loaded kitchen

Lazy Daze Beach House - Modern 5 Star Oceanfront
Private beachfront home rentals

Villa 5027 on Duck Key BOAT SLIP available

Grouper Getaway @ Ocean Isles Fishing Village

Treetops Apt.Sleep1-4 Beach Steps Away

Panoramic Ocean Views, Ocean Pointe Condo

Private Beach in Marathons Key Colony Beach

Paradise found! Sea-Esta Condo beach and pool.

Corner townhouse w/saltwater lagoon views

Cabana Club Condo: Key Colony Beach, FL
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $482 CAD | $546 CAD | $631 CAD | $443 CAD | $824 CAD | $443 CAD | $546 CAD | $521 CAD | $515 CAD | $443 CAD | $419 CAD | $471 CAD |
| 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
- Schnebly Redland's Winery & Brewery
- Calusa Campground
- Coral Castle
- Homestead-Miami Speedway
- Bahia Honda State Park
- Robbies Marina Of Islamorada
- Theater of the Sea
- Seven Mile Bridge
- Everglades Alligator Farm
- Ernest F. Coe Visitor Center
- Key Largo Kampground And Marina
- Monkey Jungle
- Florida Keys Aquarium Encounters
- Harry Harris Beach and Park
- Dolphin Research Center
- Founder's Park
- History Of Diving Museum
- Conch Key
- Homestead Bayfront Park





