Holiday rentals in Florida Keys

4.94 out of 5 average rating, 103 reviews

Apartment in Tavernier

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

4.94 out of 5 average rating, 146 reviews

Apartment in Tavernier

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!

4.96 out of 5 average rating, 104 reviews

Home in Key Colony Beach

Captain’s Quarters Ahoy Mateys! Florida, Keys

This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.

4.96 out of 5 average rating, 191 reviews

Apartment in Tavernier

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.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 108 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!

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

Guest house in Biscayne Park

4.95 out of 5 average rating, 498 reviews

Cozy and charming cottage

Our cottage is located in a very quiet residential area, 15mn to the beach (Bal Harbor area).20mn from both Miami and Fort Lauderdale Airports, Located in the backyard of the main house but separate and with an independent entry. Enjoy our tropical garden and beautiful pool, in the back of our house. Share with owner only, we give priority to our guests to enjoy it! Parking available in our front yard. No kitchen but microwave and fridge. TV, cable and WIFI. It is suggested to have a car.

4.79 out of 5 average rating, 267 reviews

Boat in Marathon

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.

4.91 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!

4.88 out of 5 average rating, 756 reviews

Flat in Miami

Luxury ICON Brickell Condo @47th Floor / POOL

This Unique and Deluxe 5-star Condo, Fully Equipped and located in the same building of the famous W Hotel, Icon Brickell, at 47th-floor with the biggest SWIMMING POOL in town. We are located on the mouth of Miami river on the sea, with amazing views of the sunrise in the morning and sunsets in the dusk. Steps from City Centre Mall, downtown, restaurants, cafés, and nightclubs. Five to six miles from Design District & South Beach. THIS IS THE PLACE TO STAY!

4.89 out of 5 average rating, 119 reviews

Houseboat in Marathon

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.

4.98 out of 5 average rating, 222 reviews

Cottage in Miami Lakes

* Lake Cottage * SpaLike Bath *

The cottage is centrally located in the serene hidden gem of Mia Lakes. Perfect for couples, solo adventurers or business travelers. You will feel hidden away from it all but yet only 5- 10 min walk from restaurants, shopping, groceries, movie theater, spa, gym etc. Our lakefront guest cottage is surrounded by lots of native plants, trees & wild life. You may swim, fish (catch & release) on the lake, as well as use of a kayak.

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Popular amenities for Florida Keys holiday rentals

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Other great holiday rentals in Florida Keys

Apartment in Key Colony Beach

4.96 out of 5 average rating, 206 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

YolandaRating, 5 stars3 weeks ago

Kim was a wonderful host. Always responsive and provided a ton of recommendations for restaurants and things to do. They really thought of everything and I was completely satisfied with the amenities. The biggest issue we had was that we couldn’t swim at the beach. Full of Sargassum every day. There are jetty’s on each side of the beach that trap it there unfortunately. Pool was warm so not very refreshing. We ended up using the outdoor showers to cool off mostly. The balcony is facing the side of the property versus the ocean, so u are looking at the building next door. Also very small and directly in the sun most of the day. None of our concerns had anything to do with our host. Just providing tips and feedback. Would highly recommend this host!

5 out of 5 average rating, 3 reviews

Home in Marathon

KCB Tropical Escape

JosephRating, 5 stars1 month ago

This was better than I expected. A very spacious 2 bedroom with large kitchen, family room. The screened in porch was huge, and a great place to have meals and watch TV and the sunrise. The fully equipped kitchen was awesome for those like us that love to cook. It was a great home away from home. This place was so comfortable and was the best we ever rented.

4.85 out of 5 average rating, 94 reviews

Apartment in Duck Key

Villa 5087 on Duck Key BOAT SLIP available

JadenRating, 5 stars2 weeks ago

Great stay, would highly recommend, home was clean and quiet. Can’t wait to come back to duck key so I can book again.

4.97 out of 5 average rating, 314 reviews

Home in Naples

Brick Enclave with Mini Golf & SPA, 5mins to beach

LindseyRating, 5 stars1 week ago

My best friend and I had a great stay! The house was perfect for what we needed. Super clean and cozy and in a great location. We will definitely be back😊

4.97 out of 5 average rating, 192 reviews

Home in Islamorada

Flakey's

EmmaRating, 5 stars1 month ago

Cheryl’s place is in the perfect location in the heart of Islamorada. Listening to the live music on the back deck to wind down every night was an added plus! Cheryl was super accommodating & definitely thinks about bettering her guests’ stay. Couldn’t recommend this place more!

4.91 out of 5 average rating, 11 reviews

Home in Marathon

Endless Summer

LisaRating, 5 stars2 weeks ago

We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.