Holiday houses in Islamorada

4.94 out of 5 average rating, 104 reviews

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

4.9 out of 5 average rating, 288 reviews

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.

4.94 out of 5 average rating, 146 reviews

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!

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 109 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

4.87 out of 5 average rating, 447 reviews

Guesthouse in Key Largo

Romantic Cabin/Guesthouse, beach Sunsets, fishing.

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"

Holiday home in Key Largo

4.99 out of 5 average rating, 210 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Superhost

Boat in Marathon

4.79 out of 5 average rating, 273 reviews

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

4.97 out of 5 average rating, 193 reviews

Home in Islamorada

Flakey's

Flakeys, short for Florida Keys is everything you would expect to find on the small Caribbean island. Its paradise! Located in the heart of Islamorada there is no need for a car. You can walk or bike to the best restaurants, bars, beaches and shops this island has to offer. On Morada Way in the middle of the Art and Culture district. Everything at Flakeys is brand NEW! All new appliances, furniture and decor. Shabby Island Chic! Affordable, super clean and you can't beat the location.

4.93 out of 5 average rating, 136 reviews

Guesthouse in Key Largo

Seaside Bungalow

Very private entire Cottage brand new walking distance to world famous Tiki Bar jet ski rentals kayaks Extremely private surrounded by exotic flowers and orchids.Less than 2 miles from Baker's Cay and close to the Key Largo and Islamorada wedding venues. We have a fully stocked home size kitchen. All the condiments coffee creamers sugar ketchup mustard etc. Giant stone shower with shampoos and conditioner and plenty of plush towels. Beach towels and chairs as well as 2 bicycles.

4.93 out of 5 average rating, 350 reviews

Boat in Islamorada

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.

4.96 out of 5 average rating, 113 reviews

Cottage in Islamorada

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

4.94 out of 5 average rating, 118 reviews

Home in Key Colony Beach

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

Holiday rentals for every style

Get the amount of space that is right for you

Apartments

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Bungalows

Intimate homes, inviting architecture

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Luxurious estates for the ultimate escape

Popular amenities for Islamorada holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Islamorada

5 out of 5 average rating, 7 reviews

Villa in Islamorada

Isla Key Lime: FREE Boat Dockage Sept-Oct Only!

Ricky Rating, 5 stars1 month ago

Key Lime Villa & Newman Hospitality were all around fantastic! We really enjoyed our weeklong stay at this beautiful property! They were a great host, very helpful and easy to deal with, super responsive too. The property itself was just as described, very nice, spacious and squeaky clean, very comfortable, we were able to settle in right away. Being big dog friendly was really nice as well, our boys were very comfortable and really enjoyed the place. We really love the pool and the fire pit area along with the dock area for sunset, it was very peaceful. Also, the location is perfect, it was right in the heart of the island so we were able to do a ton of walking to all of our restaurants and bars. We will definitely be back to stay here again for another trip soon! Thanks again to the team at Newman for making our stay a great one!

5 out of 5 average rating, 38 reviews

Condo in Duck Key

Oceanfront and Sunrise Views!

StephenRating, 5 stars1 month ago

We had an amazing stay in this wonderful Condominium! The host was absolutely fabulous - super responsive, friendly, and made sure we had everything we needed. The apartment itself was clean, comfortable, and perfectly located. The whole experience was top-notch, and we highly recommend this place to anyone looking for a great stay. Thanks again to the host for making it so special!

5 out of 5 average rating, 49 reviews

Apartment in Tavernier

When Paradise is Key: Tropical Oceanfront Condo

JoelRating, 5 stars6 days ago

We had a wonderful time staying at Michael’s place. It was exactly as described, clean, modern, and very comfortable. The attention to detail in the decor made it feel like a true home away from home. The location was perfect, close to everything we needed, yet quiet enough for a relaxing stay. Michael was a fantastic host: communicative, helpful, and respectful of our privacy. We especially appreciated the well-stocked kitchen, fast Wi-Fi, and cozy balcony area for morning coffee. We would absolutely stay here again and highly recommend it to anyone looking for a hassle-free and enjoyable stay. Thanks again, Michael!

4.98 out of 5 average rating, 81 reviews

Townhouse in Islamorada

Bayside Townhome in Islamorada with Boat Slip

SteveRating, 5 stars2 months ago

Claire had an emergency which caused her to forget to contact house cleaning but she was awesome to work with and went over and above to make it right when we told her of the problem. You won’t find a more beautiful private place to stay. Location is as good as it gets. Claire was a great host and we really appreciated it.

4.9 out of 5 average rating, 10 reviews

Apartment in Islamorada

Bungalows King Bed

CourtneyRating, 5 stars4 weeks ago

I loved it so much I booked another stay in October. Great location. Great staff. Quiet and peaceful. Walking distance to great restaurants. enough kitchen space to eat in. I was very happy with my stay.

Houseboat in Islamorada

4.5 out of 5 average rating, 10 reviews

Perfect escape to the ocean

ArnoldoRating, 5 stars2 weeks ago

Amazing place! Very peaceful and pet friendly!! The hosts are the best always available for us and always asking how we are doing if it’s everything okay! 10/10 experience don’t miss it.

4.92 out of 5 average rating, 53 reviews

Home in Key Largo

Treetops

LilyRating, 5 stars3 months ago

This place was such a nice experience. The views were gorgeous and the area was peaceful. It was really a bargain for the price. I highly recommend it!