Cudjoe Key

Cudjoe Key Hotels with Pools

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Amazing 9+Great 8+Good 7+Pleasant 6+

Top Hotels with Pools in Cudjoe Key

Check out our recommended hotels with pools in Cudjoe Key.
Most Booked
Lowest Price
Closest to Downtown
Highest Rated
Sugarloaf Key Hotel at Koa Resort
Sugarloaf Key Hotel at Koa ResortSugarloaf Key Hotel at Koa ResortSugarloaf Key Hotel at Koa ResortSugarloaf Key Hotel at Koa ResortSugarloaf Key Hotel at Koa ResortSugarloaf Key Hotel at Koa Resort
99+
Hotels in Cudjoe Key
With a stay at Sugarloaf Key Hotel at KOA Resort in Summerland Key, you'll be 7.2 mi (11.5 km) from Florida Keys Beaches and 16.2 mi (26.1 km) from Florida Keys Wilderness. This hotel is 20 mi (32.2 km) from Duval Street and 20.4 mi (32.9 km) from Mallory Square. Head down to the water and enjoy a day at the private beach, or take advantage of other recreational amenities including an outdoor pool and a hot tub. Additional amenities at this hotel include complimentary wireless internet access, gift shops/newsstands, and tour/ticket assistance. Satisfy your appetite at the hotel's coffee shop/cafe, or stop in at the snack bar/deli. Wrap up your day with a drink at the bar/lounge. To-go breakfasts are available daily from 8:00 AM to noon for a fee. Featured amenities include laundry facilities and an elevator. Free self parking is available onsite. Make yourself at home in one of the 44 individually decorated guestrooms, featuring kitchenettes with full-sized refrigerators/freezers and stovetops. Rooms have private furnished balconies. 65-inch Smart televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Conveniences include microwaves and coffee/tea makers, and housekeeping is provided on request.
Outstanding
100 reviews
9.8/10
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Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
28
with Terrace & Private Patio – 20 miles from Key West.
Hotels in Cudjoe Key
1Bd/1Ba Highrise UnitLocated in a gated community, just 20 miles from Key West, this cottage is the perfect place if you are looking to lay back, relax, and re-energize after a day of adventures and activities during your time in paradise. If you are looking for peace and quiet in a safe environment, this is the place for you.This cozy chalet has all the comforts of a home. It offers a bright and comfortable living room, 2 TVs with access to log into applications, Wi-fi, washer and dryer, kitchen equipped with everything you need to prepare your meals at home, a cozy master bedroom with ample closet space and a sofa bed for an extra guest in the living room. Enjoy the breeze from the keys on the spacious porch equipped with a dining area and comfortable chairs and end the day in the private patio surrounded by a beautiful and well-kept garden with comfortable chairs to rest and an additional dining room where you can enjoy a delicious barbecue.Our home is located in the Venture Out, on Kemp Channel, which is one of the most accessible boating channels to both the beautiful back country, as well as a quick, ten-minute ride to the open Atlantic, coral reefs, and world-famous Looe Key National Marine Sanctuary.Beautiful open water views abound! Easy access to great fishing, catching lobsters, boating, scuba diving and snorkeling. Amenities include a marina with store, boat ramps, swimming pool, spa, tennis courts, and much more, in a gated 24-hour security resort. Cudjoe Key is close to both Key West and Marathon in the section of the Florida Keys known as the Lower Keys. This provides easy access to events such as the offshore powerboat races, sailing regattas, fishing tournaments, Fantasy Fest, Star Party, and many more. The Lower Keys include well-known destinations such as Big Pine Key, Summerland, and Sugarloaf.Check in after 4pm on date of arrival and Check-out is 10am on departure date.Please note that maximum occupancy for this property is 3 people. There is a queen bed in the bedroom and a sleeper sofa in the living room which can accommodate an extra guest if necessary. No pets are allowed. No smoking is allowed inside the property and no smoking is allowed on the terrace. No inappropriate conduct or partying will be tolerated. The property is monitored by security guards. Violation of any of these rules are grounds for security to ask you to leave immediately without a refund.ADDITIONAL CHARGES:Venture Out charges a one-time resort fee upon entry of ($125.00), payable at the gate upon arrival. When you arrive at Venture Out , you will go to the Venture Out Office (or the Guard Gate if it is after hours) to pay the fee and to receive your parking pass. Credit Card or Cash only are accepted for this fee. Only one car is permitted at each lot. Transportation vehicles must fit in the driveway or will have to be moved into overflow parking for a small nightly fee. If you have an extra car you will need to park in the overflow parking lot and pay the appropriate nightly fee up to 14 days maximum pending availability. There is no jet ski trailer parking available. Boat trailer parking may be available, subject to availability and for a fee. The rates are $5-$10 per night depending on size. NO COMMERCIAL VEHICLES ALLOWED. THERE IS NO GUARANTEE, IMPLIED OR OTHERWISE, THAT VENTURE OUT WILL PROVIDE ANY OVERFLOW PARKING SPACES FOR ADDITIONAL UNIT BOAT TRAILERS OR VEHICLES. PLEASE PLAN ACCORDINGLY.IF YOU ARRIVE WITH MORE THAN THE MAXIMUM ALLOWED IN THE RENTAL UNIT, YOU WILL NOT BE PERMITTED INTO THE PARK AND NO REFUND WILL BE ISSUED.COVID-19-Related Information:- Additional cleaning measures are being enforced at all units so NO EARLY CHECK INS or OUTS will be accommodated so we can have the maximum amount set to sanitize each unit properly for the safety of our guests. CHECK IN TIMES are 4 PM and OUT 10 AM please make your travel accommodations accordingly or book a day earlier / later if arriving early or departing late.- No baggage holding will be allowed- All additional back up supplies and additional bedding will be removed from each unit to avoid cross contamination.AMENITIES: EssentialsInternetLinens providedTowels providedAir conditioning KitchenMicrowaveRefrigeratorDishes & UtensilsCoffee MakerKitchenStoveToasterOvenGrill Pool & SpaCommunal PoolCommunal Spa (for adults only) EntertainmentTelevision LaundryWashing MachineClothes Dryer Suitability:Minimum Age limit for RentersOccupancy:3 person maximum capacity - ENFORCEDAbout pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:Please review Venture Out's Rules and Regulations, found in the rental agreement section..Please fill out the Renter Registration Information Sheet, found in the rental agreement, and email it to ----@--------.--- prior to check-in..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 26.About events:No events allowed.
Outstanding
10.0/10
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Relaxing and Inviting home in gated community
Relaxing and Inviting home in gated communityRelaxing and Inviting home in gated communityRelaxing and Inviting home in gated communityRelaxing and Inviting home in gated communityRelaxing and Inviting home in gated community
7
Hotels in Cudjoe Key
The community charges a security/registration fee upon arrival to the renter. The fee will be $116.28 plus $8.72 in tax. This fee is not included in your reservation. Also, there are fees for more than one car or trailer storage. The overflow parking is a first come , first served basis.These fees are not included in the price of the home. This 2 bedroom, one bath is located in Venture Out on Cudjoe Key, FL. Featuring 35 feet of dock space on a clean canal. 23 miles outside of Key West!. Venture Out is a gated community that features a community pool, hot tub, tennis courts, basketball court, boat ramp and much more. This unit has been recently updated with paint, decor and much more. There is a dishwasher, grill, TV and free wifi. The unit includes a 2 person Kayak and Paddle board at no extra charge. Holiday and seasonal rates may differ. Please contact me for rates. Lot 439.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:You will be responsible for any damage to the rental property caused by you or your party during your stay..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Outstanding
8 reviews
9.8/10
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Cudjoe Key
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Relaxing  Home in gated community
Relaxing  Home in gated communityRelaxing  Home in gated communityRelaxing  Home in gated communityRelaxing  Home in gated communityRelaxing  Home in gated communityRelaxing  Home in gated community
17
Hotels in Cudjoe Key
This 2 bedroom, one bath home is located in Venture Out on Cudjoe Key, FL. 23 miles outside of Key West!. Venture Out is a gated community that features, community pool, hot tub, tennis courts, basketball court, a private ramp, unit is 85 yards from ramp, easy for lunching kayaks. This unit was built in 2017. There is a dishwasher, grill, TV and free WIFI. The unit includes 2 adult bikes, 2 person Kayak and Paddle board at no extra charge. ATTENTION: The community charges a security/registration fee upon arrival to the renter. The fee will be $116.28 plus $8.72 in tax. This fee is not included in your reservation. Also, there are fees for more than one car or trailer storage. Overflow parking is first come, first served basis.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About customRules:You will be responsible for any damage to the rental property caused by you or your party during your stay..About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Amazing
20 reviews
9.6/10
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Waterfront home with numerous amenities on popular Cudjoe Key!
Waterfront home with numerous amenities on popular Cudjoe Key!Waterfront home with numerous amenities on popular Cudjoe Key!Waterfront home with numerous amenities on popular Cudjoe Key!Waterfront home with numerous amenities on popular Cudjoe Key!Waterfront home with numerous amenities on popular Cudjoe Key!Waterfront home with numerous amenities on popular Cudjoe Key!
21
Hotels in Cudjoe Key
Crystal Clear Canal front home with open water view! Home is located in a desirable community called Venture Out. Fully furnished, and beautifully decorated with popular Key West colors! Spacious and bright rooms are waiting for you! 3 Beds Cable TV throughout! Master bedroom features a queen bed, full bath, TV, and storage. Guest bedroom includes two twin beds, TV, storage and stackable washer and dryer. Living has lots of windows, sliding glass doors that lead to the porch, TV, 5 electric recliners in recliner, loveseat and couch. Kitchen is nicely equipped and includes coffee pot and Keurig maker, microwave and toaster. Home has ramp in front of property, and steps in back. Porch offers beautiful views with a small seating area. Out back is seating area seawall dock has grill, fish cleaning station, and swim ladder. Seawall can accommodate a boat up to35'! We have two bikes for your use! This privately owned community offers amazing amenities that include: a guarded and patrolled gate 24/7, Recreation Hall, Pavillion, heated pool, Jacuzzi, Fishing, Diving, Tennis and Basketball courts, bocce ball, pickle ball, mini golf, Volleyball, Horse shoes, Shuffleboard and playground! Security cameras are located near the pool, jacuzzi and throughout the common areas of the property. Community events like yoga, pancake breakfasts on Saturday, pool aerobics, church bingo and more! One parking space for the home. Overflow parking is available for one other vehicle OR trailer. For convenience, be sure to visit the Venture Out Ships Store for those last minute necessities! There, you will also find two boat ramps and gas! Venture Out charges a one time registration fee of $125.00 for security and amenities of the community. It is due upon arrival and collected at the guard gate. You will be given a parking pass that needs to be displayed in your vehicle. Cash or credit card only. Book your much needed and well deserved stay, today!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.No baby items supplied. Sorry.About customRules:Please place all trash in the garbage can that's built into the ground in the front yard. No candles please..Please do not keep windows or doors open with a/c on as it may freeze up the unit.,Please load and run the dishwasher prior to departing if necessary..About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 25.About events:No events allowed.
Great
9.2/10
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Island Therapy
Island TherapyIsland TherapyIsland TherapyIsland TherapyIsland TherapyIsland Therapy
20
Hotels in Cudjoe Key
Amazing
9.6/10
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20 MINUTES TO KEY WEST , BOATERS PARADISE
20 MINUTES TO KEY WEST , BOATERS PARADISE20 MINUTES TO KEY WEST , BOATERS PARADISE20 MINUTES TO KEY WEST , BOATERS PARADISE20 MINUTES TO KEY WEST , BOATERS PARADISE20 MINUTES TO KEY WEST , BOATERS PARADISE20 MINUTES TO KEY WEST , BOATERS PARADISE
14
BOATERS PARADISE
Hotels in Cudjoe Key
COMPLETELY RENOVATED TOP TO BOTTOM , GOLF CART INCLUDED !,2 BEDROOM , 35' DOCK WITH ALL NEW PAVERS AND 13' UMBRELLA , FISH CLEANING TABLE , HOSE AND ELECTRIC AT DOCK. COMMUNITY STORE , GIANT NEW RAM, ICE, BAIT, AND GROCERY. COMMUNITY POOL AND HOT TUB. DOG FRIENDLY. GATED COMMUNITY WITH FULL TIME GUARDS. ****PLEASE NOTE THERE IS A $120 REGISTRATION FEE IMPLEMENTED BY THE ASSOCIATION AND COLLECTED AT THE GATE. About pets:Pets allowed: dogs and cats less than 50 lbs per pet (limit one pet total).About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 35.About events:No events allowed.
Amazing
48 reviews
9.4/10
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Waterfront Venture Out Home
Waterfront Venture Out HomeWaterfront Venture Out HomeWaterfront Venture Out HomeWaterfront Venture Out HomeWaterfront Venture Out HomeWaterfront Venture Out Home
11
Hotels in Cudjoe Key
Mandatory $125 Fee paid to Venture Out Community upon arrival. Waterfront home with concrete seawall for boat dockage. Open water views from the bedroom. Located in Venture Out community with many amenities including pool, kiddie pool, jacuzzi, bocce, tennis courts, pickleball, marina, dual boat ramps, playground area, convenience store, etc.Overflow parking fee for extra vehicle and or trailer 20ft and under is $5 per night, over 20ft is $10 night paid to the guard booth. Overflow parking is on first come first serve basis, not guaranteed. Must abide by community rules.About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Great
9.0/10
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waterfront cottage near key west, sleeps 6
waterfront cottage near key west, sleeps 6waterfront cottage near key west, sleeps 6waterfront cottage near key west, sleeps 6waterfront cottage near key west, sleeps 6waterfront cottage near key west, sleeps 6waterfront cottage near key west, sleeps 6
39
sleeps 6
Hotels in Cudjoe Key
This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!About this spaceThis reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat right outside your door, you will be able to enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, pickle ball, board games, wifi & roku) and of the community (Pools, spa, boat launch, sports courts, even a library and a general store!). You can use this magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!The space:Calypso Cottage is a re-imagined Florida-style mobile home. It is spacious and well appointed, with a jaunty tropical motif. The open floor plan provides perfect entertaining space with sight lines between common rooms as well as the canal front patio. The roomy screen porch offers comfortable seating amidst a lush, tropical setting. The master bedroom is oversize while the smaller bedroom still has plenty of space and lots of storage. Both beds are equipped with thick, new memory foam mattresses and there are also a queen size sofa bed and a smaller futon. The bathroom is small but fully outfitted, and for extra bathroom space there is a 24 hour bath house (absolutely immaculate!) directly across the way. Whole family need to shower at once? perfect solution. Need to do a load of laundry? there is a laundry niche with a modern washer and dryer in the cottage. Free use of Kayaks, bikes, beach gear and everything in the cottage means you'll never want to leave!Guest access:Parking at the unit is for one vehicle only. Guests can park additional vehicles in the overflow lot on a first-come first-serve basis for a small fee. This is arranged through the front gate. boat trailers are also parked in the overflow lot.It is a short walk to the common areas or guests can bike the community or travel by boat, float or other vessels in the abundant canals.Other things to note:100.00 plus tax entrance fee to the community paid on arrival. This is a flat fee no matter what the duration. This is a fee charged of every group admitted to Venture Out and has nothing to do with VRBOAbout Venture Out:Venture Out is a gated resort community located at mile marker 22 which makes it less than 20 miles to Key West and close to the key deer refuge, Bahia Honda State park and much much more. Amenities in the community include 2 pools, a hot tub, a protected swimming area, a boat launch, general store, community center with a post office and reading library, game room, tennis, pickle ball and bocce ball courts, multiple bath houses and so much more!About pets:No pets allowed.About checkOut:Check out before 11:00 AM.About children:Children allowed: ages 0-17.Canal front property.About checkIn:Check in after 4:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 21.About events:No events allowed.
Amazing
14 reviews
9.4/10
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Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
21
Hotels in Cudjoe Key
Enjoy our little peace of paradise! Come and make memories at this laid back and family-friendly waterfront home. Located in a gated community, just 20 miles from Key West, this cottage is the perfect place if you want to relax and re-energize after a day of adventures and activities during your time in the Florida Keys!VO 453 - Island Oasis Open Water Views 17' SeawallEnjoy expansive open water views from this beautiful midrise, a 2bd/1.5Ba vacation home in a highly desired 24 hour gated community. This home features a 17' seawall overlooking a 60' wide canal and Atlantic Ocean, great for launching your kayaks, paddleboards or small boat. Enjoy stunning sunrises and peaceful evenings right from your porch!Both bedrooms feature a queen sized bed and flat screen tv. The smaller bedroom is attached to a half bath. The main bathroom has a standup shower and plenty of counter space. The kitchen is fully equipped, including a coffee maker, filters, sugar and tea.Additional amenities include: Central air conditioning, ceiling fans, WIFI, streaming cable, family games, iron, dishwasher, queen size blowup mattress for the surprise extra guest/s, BBQ Grill and BBQ utensils.We are located in a spotlessly clean gated community with 24 hour security, marina, ship store, boat ramps, picnic garden, heated pool, hot tub, basketball, playground, pickle ball, bocce ball and tennis, pavilion and club house for activities, over 4 miles of paved streets.SECURITY DEPOSIT REQUIRED, NO SMOKING,7 DAY MINIMUM LOBSTER SEASON, FREE WIFI IN REC HALL, OVERFLOW PARKING ADDITIONAL FEE 14 DAYS MAX*** IMPORTANT *** WHEN ENTERING, THERE IS A ONE TIME AMENITIES FEE OF $125.00 - DUE UPON ARRIVAL. THIS FEE IS PAID DIRECTLY TO VENTURE OUT AND GOES TOWARDS ALL OF THE GREAT AMENITIES THIS RESORT HAS TO OFFER.About pets:No pets allowed.About checkOut:Check out before 10:00 AM.About children:Children allowed: ages 0-17.About checkIn:Check in after 3:00 PM.About smoking:Smoking is not permitted.About minBookingAge:Minimum age to rent: 20.About events:No events allowed.
Amazing
10 reviews
9.4/10
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See All Hotels With Pools in Cudjoe Key

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Cudjoe Key Hotels with Pools Information

Total Properties13
Number of Reviews233
Average Price (Weekdays)PKR 66,369
Average Price (Weekends)PKR 72,844