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House vacation rentals in Lower Sugarloaf Key

Find and book unique houses on Airbnb

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Popular amenities for Lower Sugarloaf Key house rentals

House rentals with a pool

Superhost

Home in Cudjoe Key

4.85 out of 5 average rating, 33 reviews

Keys Island Villa - Venture Out Home 354

SunnyRating, 5 stars3 months ago
The accommodation was exactly as described and exceptionally clean. It's a truly delightful place with a walkable area nearby. I highly recommend staying here for a pleasant experience.
Guest favorite

Home in Marathon

4.98 out of 5 average rating, 53 reviews

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

JackieRating, 5 stars2 weeks ago
Daileny's house was perfect for our family . It was well equipped and very comfortable. Unfortunately Hurricane Milton provided some uncertainty with the weather but Dailey was great at keeping us updated. The house is in a lovely residential area and although near the little airport very peaceful. A car is essential for most restaurants and activities but everything is within a few minutes drive , even a gym for my husband and son! The highlight of our week was the Sunset Tour with Marathon Mermaid , would highly recommend. Thanks again Daileny for allowing us to stay in your lovely house.
Guest favorite

Home in Key Largo

4.96 out of 5 average rating, 78 reviews

The Paradise 2

SaraRating, 5 stars6 days ago
We had a great vacation. The view and accommodations were fantastic!!!
Superhost

Home in Cudjoe Key

4.9 out of 5 average rating, 39 reviews

Cozy 2 br/2 bath home in Cudjoe

YusufRating, 5 stars3 weeks ago
It was an easy and stress free trip
Guest favorite

Home in Key Colony Beach

4.91 out of 5 average rating, 127 reviews

The Snapper House 3/2.5 45' dock sleeps 8+ pets OK

StaciRating, 5 stars1 month ago
The location was perfect if you bring your own boat! The house set up was perfect for my group with plenty of space. The only con I had was when I messaged Fred a question on day of check in he did not respond. I also messaged him about leaving early and he did not respond to that either. It seems like he has automatic messages set up to be sent at certain times during the trip about check in and check out policy and that was only time I heard from him.
Guest favorite

Home in Big Pine Key

4.9 out of 5 average rating, 68 reviews

Fishermen's Paradise | Pool, dock, gorgeous home

CassyaRating, 5 stars2 months ago
The house is huge. The view is amazing. Great location, so relaxing and peaceful. We saw Key deers walking across the yard, they were so friendly . The dock had electricity and water hose at the end, which was a big extra. Very easy to communicate with the host Karen . We also had the perfect view of a full moon rising from the ocean . It was a wonderful weekend. It exceeded our expectations.
Superhost

Home in Summerland Key

4.92 out of 5 average rating, 25 reviews

Pelico Palms Sunset Cottage

NathanRating, 5 stars4 months ago
If you’re looking for a quiet and secluded place to stay that is clean, then this is your place. I thoroughly enjoyed my time at the Sunset Cottage. Downtown Key West was a short 30 minute drive.
Superhost

Home in Cudjoe Key

4.89 out of 5 average rating, 83 reviews

Island Oasis ~ YOUR Paradise Awaits!

AlexisRating, 5 stars3 months ago
Bonnies place was located in a great location. There is a separate $125 fee that is paid upon arrival for the amenities of a pool, jacuzzi and swim area. Amazing cuban and coffee shop up the street! Kitchen was stocked and bathrooms had tolietries and plenty of towels. Good space for 4 people and additional 2 were provided an air mattress. The price we paid was a little hefty (over $400 for a night) with all fees added but we did book it 2 days before during lobster season so there wasn’t too many options available

Weekly house rentals

Guest favorite

Home in Marathon

4.96 out of 5 average rating, 24 reviews

Florida Keys Oceanside Utopia

BlakeRating, 5 stars1 month ago
This home is in a perfect location and provided quick access to the marina, gulf side and the ocean. Kitchen has everything you need for a home cooked meal. Grill outside works Back porch was our favorite place to hangout There are tons of fish right behind the house
Guest favorite

Home in Cudjoe Key

4.89 out of 5 average rating, 18 reviews

Pelican's Roost, Waterfront comfort at Venture Out

DavidRating, 5 stars2 months ago
Super clean, great cookware, great location, overall a very nice place and I would definitely come back!
Guest favorite

Home in Marathon

5 out of 5 average rating, 36 reviews

100' Dockage, Pool, Kayaks, Paddle Board, Bikes!

SarahRating, 5 stars4 months ago
Beautiful home in a great location for boating. The host was great and very accommodating.
Guest favorite

Home in Key Largo

4.92 out of 5 average rating, 13 reviews

Private Waterfront Home with lots of WATER TOYS

HillaryRating, 5 stars2 weeks ago
We loved our stay in Key Largo!! Carlos’s home was perfectly stocked and located for a great long weekend while in town to dive. Having access to the golf cart and jet skis was so convenient. He was super responsive and communicative when we feared the hurricane might impact our trip. Thankfully we were still able to come and boy are we happy we booked this house! We will definitely be back
Superhost

Home in Summerland Key

4.83 out of 5 average rating, 18 reviews

Waterfront Forever Summer house

MarkRating, 5 stars5 months ago
Beautiful house and location, especially the pool right by the seawall. Nice little Tiki hut to sit under right by the seawall. Great neighbors which is always nice. I had a boat on the seawall, 5 minutes to get out into Summerland Bay. Mike is an excellent host, extremely responsive. The TV broke after I'd been there a week. Within a day or so Mike showed up with with a huge brand new TV and installed it right away! They also brought over a couple of new Kayaks. All in all, a great experience and I'd recommend it to someone especially if they have a boat.
Superhost

Home in Cudjoe Key

4.88 out of 5 average rating, 33 reviews

Relaxing and Inviting home with 35' dock

MarshellRating, 5 stars2 months ago
it was a great place to stay.. a little confusing in the park where the place is but once we got the hang of it was ok.. the parking wasn't great we drove motorcycles 3 of us we could've easily parked all 3 in the drive way but we had to pay for 1 bike to be parked in overflow which cost more and 1 bike was over at the entrance where I couldn't keep and eye on it.. should've been better explained.. other than that was a great place people there were very nice and helpful... the lady across from us allowed us to park the bike in her driveway so we wouldn't have keep it in overflow... that was very nice ...
Guest favorite

Home in Key Largo

5 out of 5 average rating, 23 reviews

Private 2+ Acre House~Private Beach~Tiki Hut~Dock

SarahRating, 5 stars3 weeks ago
This is a fantastic Airbnb! The property is just as pictured with the beach in the backyard. The beach is perfectly appointed with lots of seating, a tiki hut, fire pit and multiple hammocks. We loved having the use of kayaks and paddle boards. The kids jumped off the end of the dock and swam with schools of little fish. The home is full of Old Florida charm and had everything we needed for our stay. The large, screened porch had many activities too and nice fans to keep cool. Kelley is a wonderful host and was very friendly and helpful. We can’t wait to visit again!
Guest favorite

Home in Marathon

5 out of 5 average rating, 7 reviews

*NEW!*Serenity Oasis~Kayaks~Bikes!~Walk2Ocean

KaylaRating, 5 stars1 week ago
The Serenity Oasis was a beautiful home! It was very easy to check in and find everything. The house had ample amenities. They had everything you needed for a beach day including beach towels, kids life jackets, beach chairs, and even sunscreen and bug spray! Their home was just as pictured and very clean. We especially enjoyed the game room on rainy days. Katie and Cody were very responsive the entire stay and even left us a sweet gift since we stayed for our honeymoon! We would definitely recommend anyone to stay with them!

Private house rentals

Guest favorite

Home in Marathon

4.91 out of 5 average rating, 11 reviews

1 Free Night-Ask Us How - Tropical Private Home

DawsonRating, 5 stars2 weeks ago
We loved staying at sandys for our honeymoon, the place was so nice, clean and private! The house is beautiful and everything was extremely clean and well taken care of. We enjoyed the hot tub and local attractions of the area were great! Sandy was super nice and responsive when needed! Instructions were clear and intuitive for check in, checkout! We will definitely stay here again when we come back!!
Guest favorite

Home in Marathon

5 out of 5 average rating, 26 reviews

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Joe & JulieRating, 5 stars2 months ago
Amanda was a wonderful host! We will definitely book her beautiful home again!
Superhost

Home in Marathon

5 out of 5 average rating, 8 reviews

Salty kisses beach house

DawnRating, 5 stars6 months ago
This is a beautiful home great for family, reunions or friend gatherings. Plenty of spaces for people to tuck away. Gorgeous view at all times of the day: sunrise and sunset. Great amenities like the light up tiki bar, barstools in the pool, and game room. Very clean and well decorated. Has everything you need including fishing equipment, beach chairs, and pool toys. Host is very responsive. Great location near Seven mile bridge, marinas, and great restaurants. Our favorite restaurant food wise was Keys Steak and Lobster, but there are many others. Don’t miss Stuffed Pig and Cracked Conch for breakfast. Fun excursions nearby included the aquarium, sea turtle rescue, and the Dolphin Research Center.
Guest favorite

Home in Marathon

4.94 out of 5 average rating, 17 reviews

Oasis Canal-Front Home: Pool, Dock, BBQ, and more!

KarenRating, 5 stars1 month ago
From check in to check out, Daymi was responsive, helpful, friendly and accommodating. We arrived a couple hours early with our boat, she allowed us to leave that a little early in the driveway so we could do errands without towing the boat around. She responded quickly with any questions we had or suggestions we needed. The home is wonderful! Beds are comfortable, water pressure is good, the ping pong and air hockey tables were a great amenity! We enjoyed a week full of manatee encounters right off the dock and fished in the comfort of the back yard! Boat dock was very accommodating and the fish cleaning station (with hose!) was a great offering for the plethora of fresh fish we enjoyed for dinner! All in all, we truly loved the home and Daymi deserves not just the 5 stars this review will allow me to give but an additional 5 stars for being one of the best hosts we have ever dealt with! God willing, we will be back for another stay!
Superhost

Home in Cudjoe Key

4.79 out of 5 average rating, 24 reviews

Wonderful Chalet - 20 miles from Key West

JulesRating, 5 stars4 months ago
Jessica was very nice and helpful. Her home was exactly as described and very clean. The only complain I have is the extremely unwelcoming security guards. I thought I was on a military base!
Guest favorite

Home in Marathon

5 out of 5 average rating, 11 reviews

Pool & Spa, Walk to Beach, Dock, Tiki, Lux Home

JosephRating, 5 stars2 weeks ago
Will definitely stay again!
Superhost

Home in Cudjoe Key

4.85 out of 5 average rating, 26 reviews

Lower Keys Paradise

MariaRating, 5 stars6 months ago
Excellent host, very responsive. The manufactured home was clean and with all what was needed for our short stay at the florida keys. Check in was fine (people at the gate are kind of rude) but our attitude helped to ease the situation. I recommend Ms. Jana's place
Guest favorite

Home in Cudjoe Key

5 out of 5 average rating, 9 reviews

Blue Heaven in Cudjoe Key #99

LoriRating, 5 stars1 month ago
We made a last-minute decision to stay here. I messaged the host, and we checked in an hour later. Hurricane Helene was making her presence known with high winds as we checked in, so we were gracious of the ability to reserve the place on such late notice. The location is in a gated community and is really easy to find. We enjoyed being right on the water. Sitting outside on the covered porch overlooking the water while drinking my morning coffee was my favorite thing. The sunrise is beautiful from the porch. The kitchen is fully stocked with all the amenities, including spices and a few pantry staples. We used the washer and dryer and they worked great. We loved this space and would stay here again.

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