
Condo vacation rentals in Islamorada
Find and book unique condos on Airbnb
Top-rated condo rentals in Islamorada
Guests agree: these condos are highly rated for location, cleanliness, and more.

Sugar Cane - Florida Keys tropical retreat
We have just completely renovated this condo at Ocean Pointe Resort and it's Insta-worthy. Every detail has been designed and considered. Sugar Cane is conveniently located near the best of the Florida Keys - close to Islamorada and Key Largo. The property boasts a large outdoor pool with a pool bar, hot tub, oceanfront beach and boardwalk, boat ramp, marina, tennis courts and children's play area. We manage Sugar Cane ourselves and live nearby so we have local knowledge and are very responsive

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.

Condo in the Keys, Peaceful ocean view retreat!
Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is close to state parks and coral reefs great for diving, fishing, and snorkeling. Relax on the private beach where kayak and paddle board rentals are available. Then enjoy a stroll on the pier to the gazebo. Splash around in the beautifully renovated heated pool and hot tub with mermaid bar! You can also enjoy food and beverages in the on-site cafe and bar

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
***9/2/25 to mid-November, building , elevator and balcony improvements will take place and our rates are heavily discounted for the inconvenience. Balcony access may be affected. No work on weekends , holidays or Thanksgiving week. All amenities are open.*** Stay at our tropical hideaway rated one of the “Coolest Airbnb’s in the Keys” by Trips to Discover! Our romantic condominium (sleeps 4) is located at the gated Ocean Pointe resort with full amenities- pool, beach, marina, tennis, cafe

SPECTACULAR VIEWS OCEAN FRONT MODERN BEACH CONDO!
Enjoy a Top Floor condo with stunning ocean views from your living room and balcony. This condo features a King bed in the bedroom, updated kitchen, a queen pull out sofa and a new washer and dryer. Enjoy the wonderful amenities the property offers to include a Large pool/ spa area or relax on the private beach with lounge chairs provided. There are lighted tennis courts, areas to grill out and a small playground. This property sits on 68 acres and one side is surrounded by a nature preserve.

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach
Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

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.

Your Happy Place - Oceanfront
Experience the ultimate coastal getaway at Ocean Point in the Florida Keys. Nestled along the Atlantic Ocean, our 2 bed/2 bath condo offers unrivaled ocean views from the moment you step inside. Indulge in the array of amenities available at our property including a private beach, pier, marina, snorkeling, family pool and a full service restaurant. Our condo comfortably sleeps 6-7 guests. Equipped with full kitchen and washer/dryer, we provide all the conveniences for a seamless stay.

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.

Toes in the Sand - 2 Bedroom Condo Sleeps 4
2-bedrooms, 2 full baths located on the 4th floor with ocean views. This condo has a beach, viewing pier, rentable boat slips, & boat trailer storage, café and a very large heated pool with a bar and gated entry with 24 hour security! Perfectly located between Key Largo and Islamorada, close to Pennekamp State Park, Harry Harris State Park, popular restaurants on the water, and the best fishing, snorkeling, kayaking, paddle boarding and diving the world has to offer at your footsteps.

Oceanfront Breeze, Stunning Views, Beach/Pool
Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

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.
Popular amenities for Islamorada condo rentals
Weekly condo rentals

Newly Renovated Piece ofParadise

Oceanside Spacious Studio Escape

Key Largo Oasis

Two Panoramic Ocean Front Views in 4314

P42 - Gulf Front condo with 3 bedrooms 2.5 baths,

Million dollar view in Key Largo!

Island Getaway at Ocean Point

2-story condo w/ panoramic bay views and balconies
Pet-friendly condo rentals

180 Degrees of Ocean Views, Lagoon and Florida Bay

Gorgeous lagoon-front 2BR Townhouse with 2 pools

Keys Getaway- 2 bedrooms w/Boat Dock, Pet Friendly

Sunrise, Award winning Ocean Front Condo

Seashells Getaway - Boat Slip, Ramp, Pool

Key Largo Condo

key Largo 3 Bedroom Townhouse Gated Community

Sunrises - Sunsets - Free Kayaks/Paddleboard
Condo rentals with a pool

Enjoy the Floirda Keys 28 nights minimum

Ocean view condo with Balcony/Ocean View

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

500 Burton Drive Tavernier, Key Largo

1BR Snowbird-friendly condo w/heated pool, BBQ, AC

Condo in Tavernier

Islamorada Oceanfront 2 bdrm, 2 bath, View, Pool

Key Largo 2 Bedroom Condo with Bay View & Sunset!
Quick stats about condo rentals in Islamorada
Total rentals
80 properties
Nightly prices starting at
€ 60 before taxes and fees
Total number of reviews
780 reviews
Family-friendly rentals
50 properties are a good fit for families
Rentals with a pool
80 properties have a pool
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Destinations to explore
- Seminole Vacation rentals
- Miami Vacation rentals
- Central Florida Vacation rentals
- Orlando Vacation rentals
- Saint Johns River Vacation rentals
- Gold Coast Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Tampa Vacation rentals
- Kissimmee Vacation rentals
- Key West Vacation rentals
- Rentals with an EV charger Islamorada
- Rentals with a washer and dryer Islamorada
- Fitness-friendly rentals Islamorada
- Apartment rentals Islamorada
- Villa rentals Islamorada
- Rentals with a fireplace Islamorada
- Family-friendly rentals Islamorada
- Luxury rentals Islamorada
- Rentals with a patio Islamorada
- Beach house rentals Islamorada
- Waterfront rentals Islamorada
- Rentals with a kayak Islamorada
- Rentals with beach access Islamorada
- Resort rentals Islamorada
- Rentals with a fire pit Islamorada
- Rentals with pools Islamorada
- Rentals with a hot tub Islamorada
- Pet-friendly rentals Islamorada
- Beachfront rentals Islamorada
- Townhouse rentals Islamorada
- House rentals Islamorada
- Rentals with outdoor seating Islamorada
- Rentals with breakfast Islamorada
- Condo rentals Monroe County
- Condo rentals Florida
- Condo rentals United States
- Everglades National Park
- Sombrero Beach
- Zoo Miami
- John Pennekamp Coral Reef State Park
- Biscayne National Park
- Coral Castle
- Cannon Beach
- Cocoa Plum Beach
- Calusa Beach & Loggerhead Beach
- Conch Key
- Theater of the Sea
- Everglades Alligator Farm
- Far Beach
- Monkey Jungle
- Sea Oats Beach
- Horseshoe Beach
- Long Key State Park
- EAA Air Museum
- Windley Key Fossil Reef Geological State Park
- Bahia Honda State Park
- Keys' Meads
- Sandspur Beach
- Long Beach
- Schnebly Redland's Winery & Brewery