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
4.98 out of 5 average rating, 47 reviews

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

KimberlyRating, 5 stars1 week ago
We had a great stay! House was neat and tidy and in a great location.
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.
Superhost
Home in Key West
4.85 out of 5 average rating, 157 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

SarahRating, 5 stars1 month ago
Had a wonderful stay for 3 nights. The house was super clean and was located right behind the pool. The house had everything you could need for a stay in the Keys, including beach towels and chairs. Our only complaint was the upstairs AC struggled to keep up, with a noticeable difference between the upstairs and downstairs. However, there were plenty of fans for us to use making this less of an inconvenience as it would have been. Overall would recommend this property for anyone who wants to stay close to Key West but far enough to have peace and quiet.
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars2 weeks 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!!!
Top guest favourite
Home in Marathon
5 out of 5 average rating, 51 reviews

Luxury Boating Paradise+Pool+Sailing Kayaks

RickRating, 5 stars1 week ago
We had an amazing family weekend here! The home was spotlessly clean, beautifully maintained, and incredibly well equipped with everything we needed. The ping pong table, video games, and sail kayaks were huge hits with the whole family. We also rented a boat, and having a private dock made that experience seamless and unforgettable. The location was quiet, safe, and perfect for quality time—cozy enough to relax, yet close to everything we needed. It truly felt like a home away from home. For all the amenities and the exceptional condition of the property, the price was a fantastic value. We’ve stayed in many vacation rentals, but this one stands out as one of the best. We’re already looking forward to coming back. Highly recommended!
Top guest favourite
Home in Key West
5 out of 5 average rating, 19 reviews

Funky Chicken Cottage with Shared Pool

LincolnRating, 5 stars1 week ago
Thank you soo much for hosting us Irene! We truly appreciate you having us. We had an amazing Key West! You were a wonderful host. I’d definitely recommend anyone book here!
Superhost
Home in Cudjoe Key
4.8 out of 5 average rating, 92 reviews

Palm Breezes! Room for Everyone on the Ocean.

GerritRating, 5 stars1 month 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!!
Guest favourite
Home in Key Colony Beach
4.95 out of 5 average rating, 20 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

KimberlyRating, 5 stars2 weeks ago
Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!

Weekly house rentals

Guest favourite
Home in Marathon
4.94 out of 5 average rating, 35 reviews

Florida Keys Oceanside Utopia

CaroleRating, 5 stars1 month ago
Shane and Kelly were fabulous! My husband and I enjoyed a week away and loved exploring Marathon. Fishing from the back deck was so much fun. We caught some mangrove snapper that we made for dinner which was exquisite! I also caught a Jack Cravalle and my hubby caught a shark. Definitely fun times! Explored beaches, hiked and went to Key West for a day. Weather did not disappoint. Highly recommend this great vacation home!
Superhost
Home in Cudjoe Key
4.84 out of 5 average rating, 45 reviews

Relaxing Home in the Keys

JamesRating, 5 stars1 month ago
We had a great time in the Florida Keys, and our stay at this Airbnb definitely made the trip even more enjoyable. The ocean is visible from the front door. The amenities that we found upon checking in were exactly what were described to us beforehand. Alain was also very quick to respond to all of our questions.
Guest favourite
Home in Cudjoe Key
5 out of 5 average rating, 6 reviews

Moana Hale Paradise #164 - Venture Out, Cudjoe Key

anthonyRating, 5 stars2 months ago
It’s awesome. The additional fees are worth it. The community is great and the commitment to keeping the neighborhood classy is excellent.
Guest favourite
Home in Marathon
4.96 out of 5 average rating, 26 reviews

Million Dollar View

JohnRating, 5 stars1 month ago
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

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

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

AnneRating, 5 stars1 week 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 Cudjoe Key
4.83 out of 5 average rating, 18 reviews

Tropical Island Getaway

DebraRating, 5 stars2 months ago
Place was sweet, kitchen and bathroom well stocked. We didn’t get an opportunity to try the pool or hot tub. 20 minutes to Key West!! We would stay there again.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars1 week ago
Loved our week-long stay at Marjorie’s! As pictured and described. Checked out the other reviews for useful tips.

Private house rentals

Guest favourite
Home in Marathon
4.96 out of 5 average rating, 23 reviews

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

HaleeRating, 5 stars6 days ago
Thank you so much for such an amazing stay! We loved the gorgeous property and all the lovely decor inside! Property was extremely clean and Sandy was so kind and helpful! We spent almost every evening in the hot tub! The home had everything we neded for an awesome week and was in a great central location, close to everything we wanted to do! We loved TJs Tiki Bar for dinner and a beautiful sunset! Thank you again Sandy! :)
Top guest favourite
Home in Marathon
4.95 out of 5 average rating, 66 reviews

Coral Lagoon #23- Private Villa Home

ReneeRating, 5 stars1 day 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.
Top guest favourite
Home in Marathon
5 out of 5 average rating, 17 reviews

Waterfront with Boat Lift/Kayaks and Hot Tub

JohnRating, 5 stars1 week 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 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!
Guest favourite
Home in Islamorada
5 out of 5 average rating, 18 reviews

Pristine pool front home w/ocean views Anglers 148

LindsayRating, 5 stars5 months ago
We recently had the pleasure of staying at this amazing beachfront house, and I can confidently say it exceeded all of my expectations! The location is simply perfect—just steps away from the water ideal for morning walks or sunrise views. The property itself is comfortable, with stylish and easy interiors that make it feel like a home away from home. The highlight was the pool—perfectly maintained and surrounded by lush greenery, offering a peaceful oasis to relax in when you want a break from the ocean. Whether you’re lounging by the pool with a book or enjoying a refreshing swim, it’s a great place to unwind. The host was also incredibly welcoming and provided thoughtful touches, from local recommendations to ensuring we had everything we needed for a great stay. I highly recommend this property for anyone looking to enjoy a relaxing beach getaway with the added luxury of a pool. Can’t wait to return!
Top guest favourite
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars2 weeks ago
Great place! Very spacious, nice dock and out door and area to enjoy with the pool! It was nice having a large deep freezer for ice and fish!
Top guest favourite
Home in Marathon
5 out of 5 average rating, 12 reviews

Waterfront Oasis w/Private Pool-Dockage-Beach

DaveRating, 5 stars5 months ago
Incredible property. Perfect gathering space for my entire family of 6. Private yet close to commerce like Publix and local gym to work out. Great memories made.
Superhost
Home in Marathon
4.89 out of 5 average rating, 64 reviews

Gorgeous Ocean View Home!

ChristinaRating, 5 stars1 month ago
We had an amazing time with our family and a beautiful Easter dinner with our friends. The location is perfect to travel all of the keys as it's just over an hour to Key West and Key Largo. The sun rose over the top floor guest bedroom with such a beautiful view of the water every day. Morning coffee with the view was awesome. Evenings spent wrapped on the couch watching movies with really nice big TV and unwinding. Sitting down by the water in evenings before sunset hanging with family watching niece play in sand was great too. Highly recommend.

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