
Beachfront holiday rentals in Islamorada
Find and book unique beachfront homes on Airbnb
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 €79 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
Top-rated beachfront rentals 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 an additional $100 per night. Ask about availability. This villa boasts breathtaking sunsets and is just minutes from watersports, charter fishing, waterfront restaurants, and local attractions, all while being surrounded by one of Duck Key’s most exclusive island neighborhoods with lush tropical landscaping. Duck Key is perfect for families or a serene couples retreat. Dine while watching spectacular sunsets from the rear deck, or explore the Middle Keys. No smoking/Pet

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.

🏝 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.

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!

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.

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 beachfront rentals in Islamorada
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

Relaxing Town home with great water views

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

Banana Cabana

Beachside Retreat w/ Pool, Boat Ramp Dock for Rent
Beachfront home rentals with a pool

Reel Large END Unit in Ocean Point Suites

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

Closest Oceanfront Home - 3 Stories, Views & Dock

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

Tropical Getaway
Private beachfront home rentals

Grouper Getaway @ Ocean Isles Fishing Village

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Treetops Apt.Sleep1-4 Beach Steps Away

Marathon 2BR Waterfront property on Resort

Panoramic Ocean Views, Ocean Pointe Condo

Private Beach in Marathons Key Colony Beach

Canal/Dock - Cabana Club - Pickleball - Remodeled

Corner townhouse w/saltwater lagoon views
When is the best time to visit Islamorada?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €300 | €339 | €392 | €275 | €512 | €275 | €339 | €324 | €320 | €275 | €260 | €293 |
| 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
- Everglades Alligator Farm
- Seven Mile Bridge
- Ernest F. Coe Visitor Center
- Monkey Jungle
- Florida Keys Aquarium Encounters
- Key Largo Kampground And Marina
- Harry Harris Beach and Park
- Dolphin Research Center
- History Of Diving Museum
- Founder's Park
- Conch Key
- Homestead Bayfront Park





