Beach house holiday rentals in Key West

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Popular amenities for Key West beach house rentals

Beachfront house rentals

Guest favourite
Home in Cudjoe Key
4.9 out of 5 average rating, 52 reviews

Keys Island Villa - Venture Out Home 354

ClaudiaRating, 5 stars1 month ago
Fantastic stay w great views. House made us feel right at home. place was in gated community. it felt safe and well maintained. Fun to walk around in the evenings.
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 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.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 11 reviews

Endless Summer

LisaRating, 5 stars3 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.
Guest favourite
Home in Key Colony Beach
4.94 out of 5 average rating, 16 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 Summerland Key
4.78 out of 5 average rating, 9 reviews

Sailfish Dream on Cudjoe Key-28 day minimum

DougRating, 5 stars2 months ago
Had a very comfortable and enjoyable stay. Accommodations were excellent. Weather was excellent! Warm balmy breezes most days kept humidity down. Lots to do, explored the keys from Islamorada down to Key West, caught the sunset. Spotted deer on Big Pine Key. A very fine month long vacation. Thank you Jeanene.
Guest favourite
Home in Cudjoe Key
4.93 out of 5 average rating, 54 reviews

Private Ocean Oasis by Key West, Florida

EricaRating, 5 stars3 weeks ago
Just what our family needed. As a new Florida resident it’s safe to say the Keys rank up there as one of my favorite places to visit. Rhonda’s home felt like our home. We enjoyed the pool and bikes. A local restaurant The Bent Prop bar and grill was a treasured find. My husband and I met the owner who is from the same area as us in Maryland. If you’ve ever wondered what Maryland Cream of Crab soup taste like… that’s the place to get it from! Can’t wait to book us again for next year!
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 179 reviews

Beachfront Villa - Florida Keys

MorganRating, 5 stars1 month ago
We had a great stay at Loretta’s place. The location offered a good jumping off point to explore the keys. The beach nearby along with canal access and kayaks was a huge plus. The garden area was nice though the mosquitos were intense. The place accommodated our group of 7 ppl well and everything was clean and well furnished. Overall, the place worked great for our group and we’d stay again!

Beach house rentals with a pool

Top Guest favourite
Home in Marathon
5 out of 5 average rating, 38 reviews

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

JillRating, 5 stars1 month ago
If I could rate this stay a 20, I would. We came across the listing last June, after wanting to try something different on our annual trip to Marathon. It looked perfect for our family. What I didn’t expect when we arrived on April 16, 2025, was to be blown away. The pictures don’t do it justice. The house is STUNNING. I felt like we were walking in/staying at a brand new house as the very first guests. The colors, the furnishings, the level of coziness brought to this luxury beach house was unmatched. The towels (bath and beach) were plush and soft. Pool speakers. The bar! I mean everything. The kitchen was stocked with what you need - high end gadgets, utensils that actually work, and every pot and pan (organized). Immaculately cleaned. And then the views. Holy guacamole. My dad parked himself on the main floor deck and didn’t move for seven days. Airbnb was right- RARE FIND. Amanda - you are the hostiest host in the world. Your communication was 💯. And we pray to make it back to yo
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 29 reviews

Luxe Super Snapper-Heated Pool, Tiki, Dock, Lanai

NickRating, 5 stars6 days ago
Book this house! Very comfortable and well stocked with everything you need from pool towels to kitchen amenities! The house is in a quiet area with ample parking and only a couple minute drive from all the restaurants and attractions Marathon has to offer. A few key features to note. The screened in pool and outdoor outdoor shower were such a nice touch after being on the boat all day, the ice machine was priceless to refill the boat coolers everyday and not have to spend a fortune on ice at the bait shop! Beds were comfortable, couch was large and accommodating for my family of 4! The house was clean and bed linens were good quality. Plenty of outdoor seating from chairs to loungers. The fish cleaning station and power plug in station for the boat were a nice touch. Vaca Cut was a short 5 minute boat ride North or you can head South by boat 5 minutes to the 7 mile bridge. We will definitely stay here again!
Top Guest favourite
Home in Marathon
4.99 out of 5 average rating, 137 reviews

Cancellation Deal: 08/02 thru 08/09

KevinRating, 5 stars1 week ago
The house was very clean and inviting upon arrival. Nice location short drive to great restaurants and local grocery stores also less than 5min walk to the beach. Mr Eddie responded in a timely manner when we had questions. All in all we had a great time and very much enjoyed our stay! Thanks Mr Eddie
Guest favourite
Home in Marathon
4.95 out of 5 average rating, 60 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars3 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!!!
Guest favourite
Home in Key West
5 out of 5 average rating, 24 reviews

Catherine House: A charming Old Town Key West

MichaelRating, 5 stars4 months ago
We thoroughly enjoyed our stay at the Catherine house and it was a perfect location to explore Key West. Beautiful space and well thought out. Perfect for two couples! A welcome retreat when you wanted to get out of the Key West hustle and bustle. We loved our time there!
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!!
Guest favourite
Home in Cudjoe Key
4.89 out of 5 average rating, 18 reviews

Oceanside home 109, dock,kayaks,bikes,pool,fishing

JeffRating, 5 stars3 weeks ago
Perfect place and really love cudjoe key
Superhost
Home in Cudjoe Key
4.86 out of 5 average rating, 93 reviews

Spanish Queen @Venture Out

ElizabethRating, 5 stars1 week ago
We had such an amazing time at this AirBB. The home was very cozy, clean and it had everything we needed for a relaxing and fun stay. The resort had wonderful amenities and beautiful scenery. We enjoyed taking the kayaks and bikes around the resort. Hana was very accommodating and responsive. I highly recommend staying here and I hope to come back one day.

Private beach house rentals

Guest favourite
Home in Marathon
5 out of 5 average rating, 37 reviews

Waterfront Escape -VACA-23-408

NatalieRating, 5 stars2 weeks ago
we were a family of 6 staying and had more then enough room. the house was perfect and had everything you needed. we enjoyed fishing off the deck and watching the manatees everyday day swimming by. the backyard was absolutely perfect to hang out and relax. Carmen is a great host and communicates fast. would absolutely stay here again.
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.
Guest favourite
Home in Key West
5 out of 5 average rating, 12 reviews

Solaris Pair-a-dise ~ A Garden Lovers Dream

CarolynRating, 5 stars6 months ago
We had a wonderful stay. Very close to Duval so we walked most places.
Guest favourite
Home in Marathon
5 out of 5 average rating, 9 reviews

Sandbox

CretiaRating, 5 stars6 days 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
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.
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 14 reviews

P36 - Charming and immaculate 2 Bedroom, 2 bathroo

BradleyRating, 5 stars3 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!
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.
Guest favourite
Home in Marathon
4.91 out of 5 average rating, 34 reviews

Viamarhe House-Private beach, Kayak, yard games

AmandaRating, 5 stars2 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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