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House vacation rentals in Sunset Key

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Popular amenities for Sunset Key house rentals

House rentals with a pool

Superhost
Home in Marathon
4.88 out of 5 average rating, 17 reviews

Salty kisses beach house

JulieRating, 5 stars1 month ago
Salty Kisses is a gorgeous home that comfortably sleeps 12 people. The kitchen is well equipped to make meals and it was an added bonus being permitted to use the washer and dryer throughout our stay. The home is well located near the best sunset view EVER as well as great beaches. The hosts were absolutely terrific to deal with. I would rent with them again in a heartbeat.
Superhost
Home in Marathon
5 out of 5 average rating, 8 reviews

Sandbox

MikeRating, 5 stars1 month ago
The stay experience exceeded our expectations. The only recommendation would be to have a listing of recommended restaurants, beaches, boat rental places, etc to go see in both Marathon and key west. We visited key west and found out afterwards where we should have gone.
Guest favorite
Home in Cudjoe Key
4.97 out of 5 average rating, 154 reviews

Cudjoe Key Home with a View

KatieRating, 5 stars2 weeks ago
Beautiful home and location. They have everything you could think of needing and staying entertained. Plenty of seating inside and out. We enjoyed the rocking chairs on the deck watching the sunrise over the water. The pool and hot tub right there across the parking lot. And so thoughtful by having a Keylime pie in the fridge to greet you.
Superhost
Home in Cudjoe Key
4.88 out of 5 average rating, 56 reviews

Cozy 2 br/2 bath home in Cudjoe

AshleyRating, 5 stars1 week ago
Marcela’s place is exactly as pictured. We had a hiccup but Marcela was extremely responsive, proactive and kind about it. We enjoyed our stay in her home, it had everything we needed - full kitchen, 2 baths, full size washer/dryer, plentiful sleeping arrangements and extra blankets, beach towels, etc. Venture Out was a quiet and peaceful place to stay with a wonderful pool and well located between Key West and Marathon where majority of our activities took place. We would book again.
Superhost
Home in Key West
4.85 out of 5 average rating, 155 reviews

Coral Hammock Poolside Home 3 bdrm 3 bath10 minute

LetíciaRating, 5 stars2 months ago
Beautiful place to stay with family and friends. The location is great. Everything was as described in the listing. We really enjoyed our time there.
Guest favorite
Home in Key West
4.92 out of 5 average rating, 106 reviews

Mango Cottage, a charming Key West home ready for

AndrewRating, 5 stars2 months ago
Lovely house, lovely week for my wife and I. The house seems recently renovated and everything was very well done, all new appliances and cabinets. Beds very comfortable. Nice quiet street aside from the planes coming in overhead but that seems unavoidable in key west.
Top guest favorite
Home in Key West
5 out of 5 average rating, 15 reviews

Funky Chicken Cottage with Shared Pool

NicholasRating, 5 stars6 days ago
Came to Key West for a long weekend with friends and couldn’t have asked for a better spot to stay. The place is spacious, clean, and comfortable. The kitchen has everything you could possibly need. Irene even left us some fresh bagels, cream cheese, coffee beans, and OJ for our first morning! The bathrooms and showers are amazing, and there is some complimentary shampoo and body soap available. Everyone had a great time and would absolutely come back and stay here again.
Superhost
Home in Summerland Key
4.88 out of 5 average rating, 34 reviews

Pelico Palms Sunset Suites

TimRating, 5 stars2 weeks ago
fantastic cottage and pool with plenty of privacy, close to the water. basically 3 master suites with adjoining bathrooms, one living area and a kitchen. really big pool deck with seating and cornhole, Webber grill and outdoor dining table. (bring bug spray). we had a great time, close to key West and Bahia Honda, a great cottage!

Weekly house rentals

Guest favorite
Home in Cudjoe Key
4.98 out of 5 average rating, 42 reviews

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

VanessaRating, 5 stars1 week ago
I stayed at Alison and Jonathan's home with my husband and 9 yr old son. Super convenient spot. Its about 35 minutes from the most southern point of the US, Duval Street, Mallory Street, and all the other touristy things to do. The restaurant super close to there Tonios Restaurant was our ultimate place to eat dinner near the water and the coffe spot Morning Joint is super close too. The actual home was just perfect has the cutest beach decor and we felt right at home. The beds were super comfy and it had everything we needed. We watched the sunrise through our window and sat outside by the deck to see the stars. We would definitely stay there again. The community has a pool and a lot of outdoor things to do within even a park.
Guest favorite
Home in Summerland Key
4.86 out of 5 average rating, 37 reviews

Powell Family Resort

AnitaRating, 5 stars11 months ago
Great property all around!! The pool was big enough for 10 people without being crowned. We utilized the kayaks, paddle boards and hammocks multiple times. The kitchen was fully stocked with everything except a blender. We even could have baked cupcakes if we wanted!! We were able to catch enough fish to have a taco night for everyone, which was an extra bonus. It was 35-40 min. to Key West, which was far enough for peace and quiet, but not too far to enjoy the fun there. We were able to walk to Kiki’s down the street, which was also nice. I would definitely recommend and stay again!
Guest favorite
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviews

Sea Turtle Cove

ThomRating, 5 stars1 week 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.
Guest favorite
Home in Upper Sugarloaf Key
4.93 out of 5 average rating, 88 reviews

Lighthouse - Beach Houses Key West

CharisRating, 5 starstoday
Stayed one night here with my husband. It was exactly as described and we even saw quite a lot of sea creatures just from the dock. Very cool and private area. Beautiful interior design! Clean! Friendly and prompt communication. So glad we stayed here!
Guest favorite
Home in Marathon
4.81 out of 5 average rating, 63 reviews

7 Mile Ocean Bliss

DawnRating, 5 starstoday
Great location in Marathon. Walking distance to a restaurant. Dock was nice to sit on and watch the fish and manatee in the bay. Wish the shuffleboard had the type of sand that allowed it to work.
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Sailors Paradise

CrystalRating, 5 stars1 month ago
Sailors Paradise was a very nice, clean with a quiet neighborhood. The house was comfortable. The back area was very relaxing with the channel right there. The kitchen had plenty of counter space. Water pressure in shower was good. Water got hot quickly. All in all a great place. I would definitely recommend it.
Guest favorite
Home in Cudjoe Key
4.9 out of 5 average rating, 41 reviews

Relaxing and Inviting home with 35' dock

MichelleRating, 5 stars1 week 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 favorite
Home in Cudjoe Key
4.92 out of 5 average rating, 52 reviews

Betty's Place

GaryRating, 5 stars1 day ago
Great spot for our first visit to the Keys! Very comfortable and super clean. In a quiet and safe (gated) neighborhood 30 mins from Key West. Loved the available activities. Played tennis every morning. The place was perfect for us. Thanks Jacqueline!!

Private house rentals

Home in Summerland Key
4.81 out of 5 average rating, 53 reviews

Kelly’s Kabin - Private FL Keys Cottage

TaraRating, 5 stars1 week ago
Really cute homey place. Was perfect for what we needed. Would definitely recommend !
Home in Marathon
4.6 out of 5 average rating, 10 reviews

Salty Air Retreat. 2/1 Half Duplex. Dockside.

stephanieRating, 5 stars25 months ago
Such a lovely home in a great location. Comfy beds and well equipped home from kitchen to deck space. Spotlessly clean with thoughtful touches such as welcome treats, beach bag and towels - even a sunshade umbrella. Great stay, great place, great host!
Home in Cudjoe Key
4.73 out of 5 average rating, 30 reviews

Wonderful Chalet - 20 miles from Key West

MariaRating, 5 stars2 weeks ago
We stayed for about a week, and were beyond happy with the house. It definitely exceeded our expectations. We felt right at home from the moment we walked in the door. All of the rooms were spotless, the house was adorably decorated and so cozy! Everything was supplied if we needed, even down to beach chairs and an umbrella. We really enjoyed our stay, and would 100 percent stay there again. The Venture Out community was so cute too, the employees were very sweet and helpful! Thank you for making us feel right at home during our lovely stay.
Home in Cudjoe Key
4.83 out of 5 average rating, 6 reviews

Heavenly Hideaway-284

DeannaRating, 5 stars2 months ago
Lovely secure location on the canal. Also close proximity to the pool, activity center and store! Lots to do or just sit on the upper patio and soak in the local beauty with your favorite beverage. Hostess was always quick to respond! We look forward to our next stay here!!
Home in Cudjoe Key
4.84 out of 5 average rating, 19 reviews

Venture Out- #10

HollyRating, 5 stars4 weeks ago
We loved the location. The view was amazing. We are very familiar with this area as we have stayed at different locations within Venture out for many years. This place had such an amazing view especially with the sunrise in the a.m. We also loved that you could relax in the sun and cool down in the shade down below. We seen alot of fun things swim up from the water and that was fun memories for our kiddos. Neighbors were extremely friendly. Throughly enjoyed our stay!
Home in Marathon
4.89 out of 5 average rating, 84 reviews

4 Bed/3.5 bath with private pool, tiki hut & dock!

SofiaRating, 5 stars7 months ago
great location and great views
Superhost
Home in Key West
4.76 out of 5 average rating, 21 reviews

Renovated Corner Unit

PatriciaRating, 5 stars1 month ago
Our stay at Paola's place was exactly what we were looking for during this getaway. The unit is spacious, open, airy, lovely and very comfortable. We enjoyed the private small deck area out back and were greeted the first morning with a rooster at the door! Many shops, restaurants and attractions are within walking distance, such as Mallory Square and the Hemmingway House. Paola's response time was immediate and a slight glitch with parking was rectified promptly. We are looking forward to our return visit!
Top guest favorite
Home in Big Pine Key
5 out of 5 average rating, 9 reviews

Hibiscus House

ChelseaRating, 5 stars3 weeks ago
Hibiscus House was such a tranquil and beautiful place to stay. The nature is so up close and personal and watching the sunrise and sunset from the wildlife refuge is a real treat. Margret was an amazing host providing a cozy stay. She relayed a quick response with any questions regarding the property that allowed us to have the best stay. If you plan your adventure here, treat the Key Deer with respect, visit The Blue Hole and enjoy the front porch sitting in the Florida Keys sunshine. Thanks again to Margret and Hibiscus House!

Destinations to explore

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  3. Florida
  4. Monroe County
  5. Key West
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