Holiday rentals in Islamorada

4.94 out of 5 average rating, 103 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, 285 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!

4.87 out of 5 average rating, 442 reviews

Guest house 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, 208 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, 267 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, 192 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, 131 reviews

Guest house 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.

4.96 out of 5 average rating, 138 reviews

Ocean View Corner Penthouse Ocean Pointe 5416

Coastal decor greets you in this serene Penthouse unit with all around views of the Atlantic ocean. This end unit is located in fabulous Ocean Pointe Suites, complete with small beach, pier, marina, large pool, jacuzzi, tennis and pickle ball court and even basket ball hoop. This unit is smack dab in the middle between Key Largo and Islamorada in the Florida Keys. Very close to amazing waterfront dining, snorkeling, diving, fishing, paddle boarding and kayaking. Must stay to believe!

4.93 out of 5 average rating, 349 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.

4.92 out of 5 average rating, 191 reviews

Home in Marathon

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in the beautiful Florida Keys! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

4.91 out of 5 average rating, 318 reviews

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

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Popular amenities for Islamorada holiday rentals

Kitchen

Wifi

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!

4.94 out of 5 average rating, 98 reviews

Your Happy Place - Oceanfront

JeffreyRating, 5 stars3 weeks ago

We thoroughly enjoyed our stay, the property was as described and the pool and bar/restaurant were great! The room in building 4 and floor 4 was perfect for views off the small balcony! Would 100% stay here again!!

5 out of 5 average rating, 41 reviews

Flat in Tavernier

Island Time at Ocean Pointe Luxe 2 King Spa BR/BA

AliciaRating, 5 stars1 week ago

Decorated so cute! Very beachy vibes! Laurie had thought of everything we needed and more! The spa shower was wonderful! We had a great time in the keys and loved our condo! Highly recommend staying here!

4.91 out of 5 average rating, 372 reviews

Boat in Tavernier

Island Sanctuary Islamorada

MelanieRating, 5 stars1 week ago

Amazing place! I loved everything about the boat and the location. Kelly was also very helpful and gave us clear instructions. A unique experience that I would recommend to anyone!

5 out of 5 average rating, 5 reviews

Oceanfront 2 bdrm, 2 bath, View, Pool, Islamorada

MichalRating, 5 stars6 months ago

We stayed here for the Thanksgiving week. The place was nice, clean, and quiet. My kids enjoyed the playroom and the pool. The condo had plenty of board games to keep the kids entertained. The Keys have lots to offer, so there is always plenty to do. Donna was very responsive, the check-in was very simple, and we had a great time. Thank you for hosting us.

5 out of 5 average rating, 75 reviews

Townhouse in Key Largo

New Listing! Tropical Oasis at the Mariners Club!

JonathanRating, 5 stars5 days ago

No joke — this was the best Airbnb experience we’ve had to date. The unit is beautifully decorated, spotless, and stocked with absolutely everything you could want or need. Clearly, every detail was thoughtfully considered. It’s just perfect! The walk to the pool is super short, and the pool itself is fantastic. Overall, an A++ stay — highly recommend!

Superhost

Apartment in Islamorada

4.77 out of 5 average rating, 91 reviews

Studio with Balcony, Kitchen, Open Living Space

AnaRating, 5 stars2 weeks ago

I loved the place. It had everything i needed and i enjoyed my stay. There was quiet during the night. I was able to wake up late since it had black out curtains. Staff was friendly and respectful. Lots to do in the near by areas. Sunset on a hammock was my favorite with a coconut drink i got at the nearby farmers market. The pool was excellent too and Very clean. Lots of parking. Will def. do it again! Great service and hospitality.