Holiday houses in Monroe County

4.9 out of 5 average rating, 420 reviews

Guest suite in Homestead

Honeymoon Suite~full kitchen & free parking

🌴Come and relax in our clean and cozy private guest suite, nested within a beautiful and safe gated community. Located just north of Key Largo, near Everglades National Park and Biscayne National Park. Whether you plan on exploring the fun city of Miami or enjoy the gorgeous Florida Keys, you will be in a great central location! Our guest suite has a luxurious and comfortable bed, high end amenities and a Smart TV. Everything you need to unwind, relax and recharge after a fun day of exploring! 😴

4.97 out of 5 average rating, 235 reviews

Tiny home in Cutler Bay

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

4.92 out of 5 average rating, 445 reviews

Cottage in Homestead

Redlands Bungalow

Newly remodeled guest house with private entrance,yard with privacy fence,patio with gas grill and dining,detached from main house.10 mins walk to RF Orchids.15 mins drive to Everglades or Biscayne Ntl Parks,40 mins to the Keys and 45mins to Miami and the beaches. Featuring 2 bdrms with superior quality mattress and TVs, Netflix included. New bathroom, washer/ dryer.The kitchen is equipped with a cook top,NO OVEN,microwave, dishwasher and a full size refrigerator. Outdoor security cameras

Superhost

Boat in Marathon

4.79 out of 5 average rating, 272 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.

4.99 out of 5 average rating, 335 reviews

Sanctuary Salt water heated pool BBQ Grill Oasis

Come and create unforgettable memories in this modernly designed single-family home with a spacious layout and a range of comfortable bedrooms. It features two king-size beds, one queen-size bed, and a twin fold-up bed, as well as an Italian queen-size sofa bed. The house is bathed in natural light and boasts modern amenities that cater to your convenience. Located in a prime location, this house is close to all the tourist areas!! The pool is salt water with heater, Also a grill area

4.93 out of 5 average rating, 134 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.

4.98 out of 5 average rating, 206 reviews

Guest suite in Miami

Peaceful & Private Miami Getaway

Escape to tranquility at our lovely Miami space. Our private space offers a serene 1 bed / 1 bath haven. Immerse yourself in a peaceful retreat adorned with modern comfort. Our kitchen invites culinary adventures, while our cozy bedroom assures restful nights. Relax in the tastefully furnished living area, complete with a TV for entertainment & a dining table meant to share moments between all guests. With a great location close to city attractions, we have the space for you!

4.91 out of 5 average rating, 322 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, 184 reviews

Barn in Homestead

Glamping Farmstyle - on a beautiful 5 acre farm!

When you come and stay with us, it’s a deeply immersive experience with our horses and chickens. Often you will find them in your front door or window. There is something profoundly impactful about being around horses and sharing close-quarters with them. You are in their energy field, receiving all that they have to offer. Without even realizing it, your energies are being grounded and regulated through their presence.

Superhost

Apartment in Marathon

4.84 out of 5 average rating, 126 reviews

Knight's Key Suites Deluxe King Room w/ Kitchen

One-of-a-kind place accommodations located next to the 7-Mile Bridge. These rooms feature one king bed that can accommodate up to two people. The room comes equipped with a kitchen. Perfect for long or short-term stays! Knights Key Suites will be performing some concrete work to the exterior facade and adding new railings, the work will be done September 3, 2024- October 10, 2024 Monday-Friday 9:00am- 5:00pm

4.98 out of 5 average rating, 796 reviews

Boat in Miami

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Apartments

Convenient locations with everyday essentials

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Monroe County holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Monroe County

4.95 out of 5 average rating, 20 reviews

Houseboat in Key West

Shanty Pineapple Key West

BlakeRating, 5 stars4 days ago

Tony was an excellent host! We are locals and did this as a staycation. Beautiful views, and really comfortable space. Highly recommend this spot! The kayak was an awesome addition, there’s a little sandbar and island close by. Would definitely do this again.

5 out of 5 average rating, 19 reviews

Houseboat in Marathon

Adventurers escape breathtaking off-grid houseboat

YulieskaRating, 5 stars3 weeks ago

Una gran experiencia, hermoso lugar. Joe fantastico. Siempre pendiente y dispuesto a ayudar.

4.89 out of 5 average rating, 79 reviews

Farm in Homestead

Unplug and Unwind in our Wine Barrel

RobinRating, 5 stars2 weeks ago

Es war ein gemütlicher Ort. Entsprach voll der Beschreibung und war schön ruhig. Uns hat es sehr gefallen und wir können es sehr empfehlen und würden es wieder buchen. Die Feuerstelle war ein schöner Platz zum verweilen.

5 out of 5 average rating, 11 reviews

Serene Meadows Ranch

YeseniaRating, 5 stars2 weeks ago

This place is a hidden gem! We really enjoyed our stay and couldn't have asked for a better weekend. The space was just amazing, both kids and adults had a blast. Jorge was an amazing host, very responsive and everything is as the listing states. Would definitely recommend.

4.94 out of 5 average rating, 17 reviews

Lake Of Dream Miami House ( New Paradise)

NatalieRating, 5 stars1 week ago

This rental is just as described! Very private and go median between Miami and the Keys. The host was very responsive and when it’s time to check out you don’t need to worry about doing anything like most other rentals. There are birds on the property and cool fish in the lagoon. My teens loved the activities and random peacocks walking around. Like other reviews stated, there are workers on the far edge of the property (it is located in a farming zone and the property is huge) but they were hardly noticed and not a bother. You can also hear low animated animal noises, maybe from the nearby Monkey Jungle, but my kids loved that too. I don’t have anything negative to say about our stay. Maybe just out of personal preference I would prefer a taller and more firm mattress in the master suite.

4.87 out of 5 average rating, 23 reviews

Houseboat in Islamorada

2/1 Aqua Lodge with Full Kitchen

CherylRating, 5 stars1 month ago

This was the first time staying on a houseboat and it was well worth it! We were only able to stay the one night to fit it into our schedule. Toni was very responsive. She even moved our stay before we checked in to another house boat because the a/c was not working in the one we booked. There were 3 of us staying and we had plenty of room. The beds were comfy. There is a deck from which you can view beautiful sky colors around sunset. We would recommend staying at this resort if you would like to switch things up from a typical hotel stay.

4.92 out of 5 average rating, 13 reviews

A new favorite house in Miami HeatedPool |GameRoom

JeffreyRating, 5 stars1 week ago

Super host, the home is an older home that has been updated beautifully, plenty to do there with or without kids. 7 of us stayed for a week and NO complaints. We will definitely be back and will recommend friends when they travel to the area.