House holiday rentals in Sugarloaf Key

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Popular amenities for house rentals in Sugarloaf Key

House rentals with a pool

Guest favourite
Home in Cudjoe Key
5 out of 5 average rating, 16 reviews

Keysie Does It at Cudjoe Key

MeganRating, 5 stars3 months ago
We absolutely loved our stay! Our checkin was smooth and flexible. The home was squeaky clean, linens and beds were unbelievably soft and comfortable, and there were more supplies/ amenities in the home than listed. We felt right at home and would love to come back! Absolutely 5 star place!
Top guest favourite
Home in Marathon
5 out of 5 average rating, 41 reviews

Discount Available! 100' Dock, Lots of Amenities!

DanaRating, 5 stars3 weeks ago
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars1 month 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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars3 weeks ago
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.
Superhost
Home in Marathon
4.93 out of 5 average rating, 61 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars1 month ago
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!
Guest favourite
Home in Key West
4.93 out of 5 average rating, 104 reviews

Paradise found

JenniferRating, 5 stars1 month ago
The house was clean and a great option for traveling as a large group. It was away from the bustle of Key West, but still easy to get around, and the restaurants nearby are delicious.
Top guest favourite
Home in Key Colony Beach
4.98 out of 5 average rating, 107 reviews

Waterfront House with 37 ft Dock & Cabana Club

MelanieRating, 5 stars2 weeks ago
Jorge’s place was super beautiful! We loved staying in key colony. Charming little neighborhood. The windows give you a beautiful view of the canal, everything was clean, we had everything we needed! We loved keeping the boat right there on the canal. We fit our large truck and trailer at the place. The patio provided lots of coverage through some rainy and windy weather. Jorge was always friendly and responsive. Also super close to the cabana club! He even left us champagne and chocolates which we enjoyed for our anniversary! Looking forward to booking our stay next year.
Superhost
Home in Cudjoe Key
4.8 out of 5 average rating, 92 reviews

Palm Breezes! Room for Everyone on the Ocean.

GerritRating, 5 stars2 months ago
10 out of 10 stay. Beautiful, serene property where we often felt we had the mangrove and key to ourselves. Several days were spent on a recurring rotation of kayaking, pool, hot tub, repeat. Perfect distance from Key West for adventuring there, but plenty on Cudjoe Key and Big Pine if you don't want to venture to the hustle and bustle. Sincerely hope to return!!

Weekly house rentals

Guest favourite
Home in Cudjoe Key
4.98 out of 5 average rating, 47 reviews

Waterfront 35’ Dock,80’ pool,20 min Key West

KimberlyRating, 5 stars2 weeks ago
We had a great stay! House was neat and tidy and in a great location.
Top guest favourite
Home in Marathon
4.95 out of 5 average rating, 66 reviews

Coral Lagoon #23- Private Villa Home

ReneeRating, 5 stars2 weeks ago
Wonderful Stay! Place was super clean and nicely decorated with minimal decor. (Sometimes places are over decorated and busy) Beach Towels were provided. Kitchen was organized & clean. Pool was nice! We brought our small dogs and the grounds were very pet friendly. Jessica’s recommended list of restaurants was spot on! Had a great time eating at several of the places. Would visit again and recommend to others.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 25 reviews

Private Home,Hot Tub,BBQ.Boat & RV Parking FL Keys

CarolRating, 5 stars1 week ago
Sandra’s conch cottage was comfortable and beautiful and very clean. Provided all the necessary items for the week. The location of the house in Marathon is perfect to all amenities. I would definitely come again.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

KCB Tropical Escape

JosephRating, 5 stars2 months 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.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Vaca Vista 3

DoreenRating, 5 stars2 months ago
What a wonderful place to vacation. My entire family had a fabulous time. A bonus was seeing the manatees in the canal. The home was very clean and was very spacious. We all highly recommend this home!!
Guest favourite
Home in Cudjoe Key
4.95 out of 5 average rating, 20 reviews

Sea Turtle Cove

ThomRating, 5 stars2 months ago
Philip's listing described the place perfectly. Zero unexpected surprises and it had absolutely everything to make our vacation super enjoyable. When it comes to location, so much to do in under 30 minutes. Smack dab in the middle when it comes to driving to Marathon or Key West. It was also great to be able to keep a boat right outside and to have a marina as part of the park. Access to great places to fish are 15-30 minutes away.
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 59 reviews

Cozy 2 br/2 bath home in Cudjoe

MariannRating, 5 stars1 month ago
Marcela's place was exactly as described and very clean. One master bedroom with master bath, and another bedroom with a twin/trundle bed, and sofa in living room. Kitchen had good amenities with cutlery and glasses, etc. We didn't use the washer but the dryer was very handy for drying bath towels and pool towels. We sat outside in the back yard the first night and heard a mysterious animal call, we thought it was a bird but then using google we found out it was a tokay gecko! So cool. We used the large saltwater pool which was very very nice. It's just a short drive to several great restaurants in neighboring keys, and we made a day trip to Key West which was awesome! I recommend Tonio's Seafood Shack & Tiki Bar, great key lime pie. Forks & Stix is a great little sushi place with great lemonade, Island Fish Company in Marathon had a great outdoor vibe right on the water. Best beach is Bahia Honda State Park. Note there is a $125 community fee upon check-in to the resort.
Top guest favourite
Home in Key Colony Beach
5 out of 5 average rating, 85 reviews

“La casa azul” step 3’ to a private pool

RickRating, 5 stars3 weeks ago
We spent an amazing week in this home. Very comfortable and quiet. The pool was amazing. Will definitely be back.

Private house rentals

Top guest favourite
Home in Marathon
5 out of 5 average rating, 18 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars3 weeks ago
The place was amazing!! plenty of room for our family of 5. All of the fishing equipment was awesome!! From the rods and tackle, to the deep freezer with bait, the extras made the whole trip more enjoyable. Loved the house. It was perfect!!! Will definately be back in the future!! 10 out of 10 would recommend!!
Guest favourite
Home in Marathon
5 out of 5 average rating, 9 reviews

Sandbox

CretiaRating, 5 stars1 week ago
⭐️⭐️⭐️⭐️⭐️ Absolute Paradise in the Heart of the Keys! Our stay at this vacation house in Marathon was nothing short of incredible. From the moment we arrived, we felt like we had found our own private slice of paradise. The house was spotless, beautifully decorated, and had all the comforts of home—plus the added bonus of breathtaking ocean views and island vibes. The location couldn’t have been better. Tucked away in a peaceful part of Marathon, we were just minutes from everything—the beach, boat rentals, amazing restaurants, and the iconic Seven Mile Bridge. The property itself was incredibly well-equipped: a fully stocked kitchen, super comfortable beds, high-speed WiFi. What really made this place stand out was the outdoor space. The private dock was perfect for fishing and sunset cocktails, and the pool made it hard to ever want to leave. We even spotted dolphins just off the dock one morning—unreal! The hosts were friendly, responsive, and went out of their way to make sure we
Top guest favourite
Home in Marathon
4.97 out of 5 average rating, 39 reviews

Grouper Getaway @ Ocean Isles Fishing Village

JessicaRating, 5 stars6 days ago
One of the best airbnbs we have stayed in. They had everything including paddle board, kayak, bikes, bogg bag, yeti cooler, fishing gear, bait cooler full of bait, fishing poles, life jackets, and even sunscreen. Also anything you could imagine for a kid (pack and play, stroller, toys). Will definitely be returning.
Superhost
Home in Summerland Key
4.59 out of 5 average rating, 86 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

JessicaRating, 5 stars2 days ago
Great spot for our family. Lovely to be right on the water and walking distance to Kiki's Sandbar--where they cooked our fresh catch! The screened-in porch has a huge table, ceiling fan to keep the air moving and a great view. It's not luxe, it's a family place--clean, comfortable, in an awesome location with beautiful sunrise views, and the kitchens have everything you need. The two units are completely separate and you need take outdoor stairs to get between the units. We put the teenagers downstairs and the parents upstairs. If kids were younger, that wouldn't have worked. Both units have a kitchen, bathroom and laundry. Wifi was fast and reliable. Winn Dixie is 5 min away for groceries. Close to Bahia Honda, 25 min to Key West and 5 min boat ride to Picnic Island. Alex was super responsive to questions throughout our stay.
Guest favourite
Home in Key Colony Beach
4.94 out of 5 average rating, 17 reviews

Paradise Cove!30ft Dock Pool BBQ

BryceRating, 5 stars1 month ago
Had a great week at Yunis place! Her house was extremely clean and had everything we needed and more especially for cooking which was nice. She had probably the most comfortable bed, sheets and pillows I’ve ever used. I loved how it was clutter free and didn’t have any breakable decorations down low around since we had our two toddlers with us. The pool was the perfect size for us and it was great to relax outdoors. We even saw Manatees swim up to the dock. 10/10 would recommend this spot.
Guest favourite
Home in Key Largo
5 out of 5 average rating, 15 reviews

NEW! Oceanside Casa Largo Modern Tropical Getaway

AnnabelaRating, 5 stars1 month ago
amazing stay at Martha's place. it's prestine. she's super responsive and very kind. I'd stay at any of her places because she's on top of it.
Superhost
Home in Cudjoe Key
4.86 out of 5 average rating, 43 reviews

Relaxing and Inviting home with 35' dock

MichelleRating, 5 stars2 months ago
The place was small and cozy fit our family of five, just 30 minutes from Key West and about 30 minutes from Marathon. Venture Out has a heated pool, heated kids pool, and hot tub as well as a Lagoon to swim in. . Lots of amenities in the rec room as well as tennis courts, pickle ball, and a small playground . There are nearby restaurants. Location was great!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars3 weeks ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

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