Top 5 Holiday home in Monroe County

99360 Overseas Hwy, Key Largo, FL 33037, United States

“We stayed in cottage 8. Simple couples accommodation with comfortable bed. Full kitchen a big bonus. Private beach area to watch the sunset, that's never crowded. Complimentary kayaks. Outstanding/helpful service from Gisela and her …”

160 Sterling Rd, Tavernier, FL 33070, United States

“This was a very beautiful place to stay! The staff were extremely helpful and friendly and the rooms were always very clean. The resort is right next to the beach which makes it the perfect place to relax and just read a good book. They …”

198 Harborview Dr, Tavernier, FL 33070, United States

“This inn was a wonderful experience all around! The location is idyllic and calm, looking out on a small inlet in the Gulf of Mexico. The beach has hammocks, a fire pit, a bungalow, and numerous chairs throughout all facing the western edge of the property for the ever changing sunsets over the Gulf. I spent hours in the hammocks and loved every minute relaxing there! The room we stayed in was quaint and appropriately decorated in tropical decor and looked out on the beach. The best thing about the room was the ability to walk directly out onto the beach (Sandpiper Room 3). While the price may seem steep for some, you get SO much for the price you pay. Everything I listed above plus kayaks, paddle boards, a heated pool with 24/7 access, and bikes! Given how much I loved this inn, we will definitely be staying here in the future!!”

1327 Duval St, Key West, FL 33040, United States

“Great location! Breakfast was decent. Our room was easily accessible. There was a pool we didn’t get to use. due to our short stay but overall great place. Just steps away from the southern most tip *photo op*”

1212 Simonton St, Key West, FL 33040, United States

“Due to flight cancellations from winter storms, we stayed in three different rooms in one week. The rooms are compact, but luxurious. All three rooms, from the superior pool suite, to the regular pool suite, and the balcony suite, were …”

6000 Peninsular Ave, Key West, FL 33040, United States

“Warm and inviting!!! Clean and pretty spot! They serve adult drinks from Jack's lounge, but the only downfall is there is not a place to grab a bite to eat! Bring your cooler with sandwiches pre made from publix 😋 We did, and it was perfect! Enjoy!!! …”

701 Spanish Main Dr, Cudjoe Key, FL 33042, United States

“How can you go wrong? Best view ever. What a great house for 2 couples (could have held another)! The owners of this property must be incredibly attentive to the maintenance of their “home away from home”. Everything WELL DONE!|The resort …”

2950 Overseas Hwy, Key West, FL 33040, United States

“I expected better. The sites on the water and overall RV park were beautiful. Our daughter stayed in Site 7 and we could see Site 8 and they were amazing and updated and clean. Site 47 was awful. The furniture was old and moldy and the refrigerator and bar were dirty. See the pictures below. Someone told us it belonged to someone who was never there. If so, management needs to check these things before they are rented for $350 a night. The pool and laundry facilities need updated and cleaned. We had nice neighbors and met nice owners and people, but it did feel a little like big brother was watching. My husband went to rinse off our RV when management appeared five minutes later and told us we needed to pay $20. Okay. I guess the $350 we paid per night did not cover those extra five gallons of water? We paid it. No problem. But seemed a little silly. We left two days early and cancelled a six week reservation for next year.”

95320 Overseas Hwy, Key Largo, FL 33037, United States

“We stayed here during my 2 grandsons Scuba Diver training. The place is exceptionally clean. The staff is personable, accommodating and welcoming. The beds are very comfortable. The kitchenette has cutlery, dishes, hot plate, frying pan, a sauce pot, and microwave. They have free paddle boards, kayaks and bicycles. There are also outdoor grills. The place is like an offbeat tropical oasis and very quiet. It is also centrally located to everything on the island.”

511 Eaton St, Key West, FL 33040, United States

“My wife and I stayed here in October 2023. The short of it is - we absolutely loved our stay. We were nervous going in because it feels like online reviews can be hit or miss. But everything at Old Town Manor was an incredible experience. First of all, the location cannot be beat. You're steps away from Duval, but not so close that there's constantly people coming by or constant noise. The staff was so kind and helpful (Doc the cat was also great). Breakfast was delicious and was so enjoyable to eat in the adorable courtyard. And the room was great - full of character and very comfortable. Old Town Manor didn't disappoint.”

4 Woodward Way, Key Largo, FL 33037, United States

“My husband and I had the pleasure of having our wedding at Dream Bay. We honestly wouldn’t have had it anywhere else! It was the most amazing weekend and everything was so perfect and special. Lana was truly such an amazing person to work with and she took such good care of us and was so helpful leading up to the wedding, she gave me so much relief! All of our guests were so in love with the venue and their stay on the property. Everything was so well maintained and clean. We experienced the most beautiful sunsets, especially on our wedding day. I would 1000% recommend this venue for your special day or for a weekend getaway!”

1435 Simonton St, Key West, FL 33040, United States

“We had a great stay here for the week. It was nice to have the little bit of beach to chill on in the morning then head out on the town before lunch. The food and drinks are a little more expensive than other restaurants and bars, but to be expected. The front desk were very nice and accommodating, quickly addressed anything we needed and even looked up my rewards account so I could get the points.”

820 White St, Key West, FL 33040, United States

“Such a perfect place to stay, right in the middle of everything! They have bikes to rent which is super convenient as its just a short bike ride to anything you want to see. The staff are all super kind, we especially had a great experience with Indra - we had a ton of questions and she was always ready to help and super kind! The rooms are great, looks like they have recently remodeled as they are even better than the pictures! Only thing, wish the room had a microwave. Pool was nice as well. Overall a terrific stay and perfect place to experience Key West!”

601 Caroline St, Key West, FL 33040, United States

“We love this place! Location location location. Super close to Duval street but not too close. Which is good because every single bar and restaurant has live music. We enjoyed the heated pool so much after a rainy wintery day at the beach. The three stars are because our room wasn’t made in the three days we were there.”

622 Fleming St, Key West, FL 33040, United States

“This b&b is very conveniently located near Duval street and all the old town points of interest. Yet it is in a surprisingly quiet and calm neighborhood. The checkin procedure was very easy and we were lucky to find a parking spot. It cost …”

99306 Overseas Hwy, Key Largo, FL 33037, United States

“A quaint little village of beautifully hand-painted cottages. Jenn welcomed us immediately upon our arrival and made us feel just like family. Everyone is so friendly and the amenities are plentiful (sailboats, kayaks, paddle boards). Rooms are super clean and comfortable. Thank you for a wonderful stay and we hope to be back soon!!”