Vacation rentals with a patio in Cudjoe Key

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Top-rated patio rentals in Cudjoe Key

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Guest favorite

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 38 reviews

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Dec 3 – 10

G$63,415 GYD per night

Guest favorite

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Residential Condominium! Is located on a 60' wide canal, our Dock is 35 feet. With fish clean table, cleats, bumpers and patio table with 4 chairs. Two porches for outdoor enjoyment over looking the water and front yard. Just a few steps from the pool, hot tub (please be aware that they can close the pool and hot tub for emergency/ regular maintenance without any notice), marina, store, rec hall, tennis. And 23 miles from Key West!

Apr 8 – 15

G$83,321 GYD per night

Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 79 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

Jul 19 – 26

G$160,661 GYD per night

Superhost

Vacation home in Key West

4.87 out of 5 average rating, 230 reviews

Historic Cigar House. 3rd floor Suite W/Kitchen

This unit is located in the historic "Cigar House" of the Island City House Hotel. Unit 12 is on the 3rd floor and is one of the most requested units in the entire hotel. Your private balcony overlooks the pool. Only 3 blocks from Duval street so close everything, yet quiet enough for a good nights sleep. You will have your own private entrance and use of all the hotel amenities. The space is a private 1BR with a kitchen and NEW sleeper sofa (12/23). In Old Town, walk to everything.

Apr 10 – 17

G$79,429 GYD per night

Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

This brand new 5/6 bedroom 4 bath oceanfront home has a private pool and huge outdoor living space. There is beach access, shared dock space and an outdoor gazebo to watch sunsets. You can bring up to a 24' boat or paddle out on one of the shared kayaks onsite. Fully equipped kitchen, linens, beach towels, a propane BBQ grill and 2 washer/dryers. This home is priced based on the number of guests. The base rate is for up to 6 guests. Additional guests fee is $25 per night per person.

Nov 9 – 16

G$143,796 GYD per night

Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 49 reviews

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $113 directly to security upon entry into the park***

Jan 7 – 14

G$80,084 GYD per night

Superhost

Villa in Marathon

4.89 out of 5 average rating, 146 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Aug 29 – Sep 5

G$79,036 GYD per night

Guest favorite

Townhouse in Key West

4.91 out of 5 average rating, 109 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the Seaport and world famous Duval Street! Bikes, kayaks, paddle boards and golf carts can be rented locally

Apr 19 – 26

G$89,371 GYD per night

Guest favorite

Camper/RV in Big Pine Key

4.93 out of 5 average rating, 41 reviews

Having fun in the lower Keys

Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

Aug 31 – Sep 7

G$25,233 GYD per night

Superhost

Home in Cudjoe Key

4.88 out of 5 average rating, 73 reviews

Island Oasis ~ YOUR Paradise Awaits!

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!

Mar 22 – 29

G$73,641 GYD per night

Superhost

Home in Cudjoe Key

4.92 out of 5 average rating, 12 reviews

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

Bring your boat to this charming two bedroom home with 35’ sea wall! Direct access to some of the best fishing and snorkeling in the Keys! Beautiful neighborhood loaded with amenities. Our home renovation was completed in late 2023. Visit YouTube “The Barnacle at Venture Out” filmed during renovation.

Dec 21 – 28

G$90,146 GYD per night

Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 33 reviews

Keys getaway

Relax with the whole family at this peaceful place to stay. Welcome to Florida Keys. This house is 1 bedroom with 1 .5 bath sleeps 6 Large, screened lanai overlooking canal with direct access to Atlantic Ocean. Cudjoe Key fishing is one of the best in Keys! 35 ft seawall

Oct 3 – 10

G$69,856 GYD per night