Compare vacation rentals in Cudjoe Key, FL from 100+ sites!

438 available vacation rental offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Cudjoe Key, FL vacation rentals
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

Best Vacation rentals and Airbnb offers in Cudjoe Key, FL

Best Cudjoe Key, FL vacation rentals with a balcony

Casa Kiwi #472 - Ocean Views On Cudjoe Key - Cudjoe Key, FL
10 2 reviews
Cudjoe Key, FL
06/18 – 06/29
$333/nighttotal: $3663 (11 )

Casa Kiwi #472 - Ocean Views On Cudjoe Key

2 2
apartment , Cudjoe Key
Casa Kiwi, located in the Venture Out community on Cudjoe Key, offers ocean views and is a short 20-minute drive from Key West, near restaurants like the Square Grouper and Morning Joint.
This 860-square-foot vacation home features two bedrooms (King and Queen), two bathrooms, a modern kitchen, private pool, Jacuzzi, tennis court, and four bikes, accommodating up to six guests.
Vo 173 2 Bed 2 Bath Silt Canal-front, Ocean View - Cudjoe Key, FL
9.8 77 reviews
Cudjoe Key, FL
10/14 – 10/20
$456/nighttotal: $2736 (6 )

Vo 173 2 Bed 2 Bath Silt Canal-front, Ocean View

2 2
apartment , Cudjoe Key
This canal-front vacation home, located in Summerland Key near Cudjoe Key, offers direct Gulf and Ocean access via a 35-foot seawall and proximity to Florida Keys attractions.
This 900-square-foot rental boasts two bedrooms, two bathrooms, sleeps six, and includes a private dock with ocean views, a swimming pool, tennis court, and features such as a full kitchen, washer/dryer, and free Wi-Fi.
Key Lime Hideaway - Oceanfront Gated Community, Amenities, 3br Stilted Retreat - Cudjoe Key, FL
Cudjoe Key, FL
10/14 – 10/20
$365/nighttotal: $2190 (6 )

Key Lime Hideaway - Oceanfront Gated Community, Amenities, 3br Stilted Retreat

3 2
apartment , Cudjoe Key
This three-bedroom, two-bathroom Cudjoe Key vacation rental, located in the gated Venture Out community, offers easy access to Key West (20-minute drive) and other Florida Keys attractions.
The 840-square-foot stilt home features ocean views from dual porches, a private patio, a fully equipped kitchen, and community amenities including a pool, Jacuzzi, tennis courts, and a marina store; it comfortably sleeps six guests.
Wonderful Chalet, With Terrace & Private Patio  20 Miles From Key West. - Cudjoe Key, FL
10 44 reviews
Cudjoe Key, FL
10/14 – 10/20
$294/nighttotal: $1764 (6 )

Wonderful Chalet, With Terrace & Private Patio 20 Miles From Key West.

1 2
cottage , Cudjoe Key
This smoke-free cottage is located in Summerland Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, and less than four miles from Florida Keys Beaches. This "Little Gem In Paradise" is rated excellent by guests and offers a peaceful garden setting perfect for relaxing.
This one-bedroom, one-bathroom cottage can accommodate up to four guests and features a private garden, terrace, and patio. Enjoy amenities like a fully equipped kitchen, washer/dryer, free WiFi, a swimming pool, a tennis court, and barbecue grills.

Guest-Favorite Family Vacation Rentals in Cudjoe Key, FL

Find the perfect family vacation rental or Airbnb in Cudjoe Key, FL with plenty of room to spread out near local beaches.

Oceanfront 2br Retreat | 35' Dock, Open Views, Boater's Paradise - Cudjoe Key, FL
9.6 53 reviews
Cudjoe Key, FL
10/14 – 10/20
$590/nighttotal: $3540 (6 )

Oceanfront 2br Retreat | 35' Dock, Open Views, Boater's Paradise

2 2
apartment , Cudjoe Key
Coconut Telegraph #221 is a 2-bedroom, 2-bathroom condo located in the Venture Out resort community on Cudjoe Key, offering direct open ocean waterfront with a 35-foot concrete dock and a 20-minute drive to Key West. This 860 sq ft residence accommodates up to 4 guests and features central air, Wi-Fi, a full kitchen, an outdoor propane grill, and access to resort amenities including a heated saltwater pool, hot tub, and sports courts, with proximity to Looe Key for snorkeling and diving.
Relax By Florida Keys Beaches, Just A 7-min Drive Away - Cudjoe Key, FL
9.8 207 reviews
Cudjoe Key, FL
10/14 – 10/20
$306/nighttotal: $1836 (6 )

Relax By Florida Keys Beaches, Just A 7-min Drive Away

2 2
apartment , Cudjoe Key
This waterfront vacation home is located in Cudjoe Key, Florida, within a 15-minute walk of Venture Key and Venture Out Keys, and within 6 miles of Upper Sugarloaf Key and Florida Keys Beaches.
This 2-bedroom house comfortably accommodates 5 guests and features a private pool, a spa tub, and a fully equipped kitchen with a refrigerator, oven, stovetop, and microwave.
Open Water Views |  32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape - Cudjoe Key, FL
9.0 2 reviews
Cudjoe Key, FL
10/14 – 10/20
$396/nighttotal: $2376 (6 )

Open Water Views | 32' Boat, King Beds, Fish Cleaning Station, Waterfront Escape

2 2
apartment , Cudjoe Key
This waterfront condo is located in Venture Out on Cudjoe Key, a private gated community, approximately 20 miles from Key West and 10 miles from popular Florida Keys restaurants.
This 860 sq ft condo offers 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests with direct waterfront access, a 35' seawall for boats up to 32', a private fish-cleaning station, and full access to Venture Out's resort amenities.
3 Night Minimum! Spectacular Ocean Views! - Cudjoe Key, FL
8.6 29 reviews
Cudjoe Key, FL
10/14 – 10/20
$400/nighttotal: $2400 (6 )

3 Night Minimum! Spectacular Ocean Views!

2 2
apartment , Cudjoe Key
This Cudjoe Key vacation home is located in Summerland Key, a short walk from Venture Key and within 10 kilometers of Upper Sugarloaf Key and other Florida Keys beaches. Travelers will enjoy the peaceful and laid-back ambiance of the surrounding area. The house has received very good user ratings.
The house has two bedrooms and two bathrooms, comfortably accommodating up to six guests. Enjoy modern amenities such as free Wi-Fi, a fully equipped kitchen, a private pool, a tennis court, and a barbecue grill, perfect for al fresco dining.

Frequently Asked Questions about vacation rentals in Cudjoe Key, FL

Destinations nearby

Best Cudjoe Key, FL vacation rentals with parking

Seascape Vacation!!! - Cudjoe Key, FL
8.3 70 reviews
Cudjoe Key, FL
06/18 – 06/29
$210/nighttotal: $2310 (11 )

Seascape Vacation!!!

1 2
apartment , Cudjoe Key
This waterfront vacation home is located on Cudjoe Key, just a short walk from Venture Key, Venture Out Keys, and Out Key, with Florida Keys Beaches a quick drive away. Guests have consistently rated this property as very good for cleanliness and location, and excellent overall.
This 1-bedroom, 1-bathroom property offers 730 square feet of space, comfortably accommodating up to 4 guests. Enjoy amenities like a swimming pool, jacuzzi, and a fully equipped kitchen, perfect for relaxing and enjoying the beautiful Cudjoe Key surroundings.
The Lookout #659 Venture Out - Gated Community - Cudjoe Key, FL
9.8 24 reviews
Cudjoe Key, FL
10/14 – 10/20
$304/nighttotal: $1824 (6 )

The Lookout #659 Venture Out - Gated Community

2 2
apartment , Cudjoe Key
This Cudjoe Key vacation rental, located in the gated Venture Out community, is a short 20-minute drive from Key West and offers oceanfront access to resort amenities including a heated pool and hot tub.
The two-bedroom, two-bathroom condo features a fully equipped kitchen with a dishwasher, a BBQ grill, and sleeps four guests comfortably, providing access to tennis, pickleball, and other recreational facilities within the community.
Mermaid House - Venture Out Lot 089 - Cudjoe Key, FL
9.4 3 reviews
Cudjoe Key, FL
06/18 – 06/29
$437/nighttotal: $4807 (11 )

Mermaid House - Venture Out Lot 089

2 2
apartment , Cudjoe Key
Mermaid House, a waterfront home in Summerland Key, offers easy access to Bahia Honda State Park and other Florida Keys attractions.
This 860-square-foot house features two bedrooms, two bathrooms, and accommodates up to six guests, boasting a private dock, swimming pool, Jacuzzi, and proximity to kayaking and snorkeling.
Cottage With Swimming Pool And Dockage, Just Minutes To Key West! - Cudjoe Key, FL
9.0 314 reviews
Cudjoe Key, FL
10/14 – 10/20
$270/nighttotal: $1620 (6 )

Cottage With Swimming Pool And Dockage, Just Minutes To Key West!

1 2
cottage , Cudjoe Key
This Cudjoe Key oceanfront cottage, located within three miles of Upper Sugarloaf Key, Upper Sugarloaf Sound, and Venture Key, offers stunning ocean views and easy beach access.
This 390-square-foot, one-bedroom, one-bathroom vacation home sleeps two guests and features a fully equipped kitchen, laundry facilities, a patio, a swimming pool, and on-site barbecue grills.

Check Out Vacation Rentals with a Pool in Cudjoe Key, FL

A vacation rental with a pool in Cudjoe Key, FL is the ideal way to complement your daily coastal adventures.

Judy's Place ~ 2 Bedroom, 1 Bathroom Home In Venture Out Community! - Cudjoe Key, FL
9.0 14 reviews
Cudjoe Key, FL
10/14 – 10/20
$254/nighttotal: $1524 (6 )

Judy's Place ~ 2 Bedroom, 1 Bathroom Home In Venture Out Community!

2 2
apartment , Cudjoe Key
This two-bedroom, one-bathroom apartment rental in Summerland Key, near Cudjoe Key, offers convenient access to Blue Hole and Wilhelmina Harvey Park.
The 670-square-foot unit at Venture Out Resort features a kitchen with a fridge and microwave, a terrace, a swimming pool, pet-friendly accommodations for two small dogs under 40 pounds, and sleeps up to six guests with two queen beds and a sleeper sofa; on-site amenities include tennis and pickleball courts, a heated pool, a spa, and BBQ grills.
Paradise Palms In Cudjoe Key #635 - Cudjoe Key, FL
9.9 23 reviews
Cudjoe Key, FL
10/14 – 10/20
$281/nighttotal: $1686 (6 )

Paradise Palms In Cudjoe Key #635

1 2
apartment , Cudjoe Key
This Keezy home is located in the Venture Out gated community on Cudjoe Key, 19 miles from Key West, offering easy access to local restaurants and attractions.
The two-bedroom, two-bathroom vacation rental sleeps five, features a fully equipped kitchen with stainless steel appliances, a private porch, and access to community amenities including a heated saltwater pool, hot tub, and marina.
Sirena Key Cottage In Venture Out - Cudjoe Key, FL
8.0 18 reviews
Cudjoe Key, FL
06/18 – 06/29
$363/nighttotal: $3993 (11 )

Sirena Key Cottage In Venture Out

2 2
apartment , Cudjoe Key
This Cudjoe Key condo rental boasts a waterfront location, a 15-minute walk from Venture Out Keys, Venture Key, and Out Key, and 2.4 miles from Florida Keys Beaches.
The 860-square-foot apartment features three bedrooms, two bathrooms, sleeps six, and includes a furnished balcony, swimming pool, jacuzzi, and free WiFi in common areas.
Waterfront Fl Keys Cottage @ Venture Out - Cudjoe Key, FL
9.5 64 reviews
Cudjoe Key, FL
10/14 – 10/20
$299/nighttotal: $1794 (6 )

Waterfront Fl Keys Cottage @ Venture Out

1 2
apartment , Cudjoe Key
The Keys Cottage 116 is located on Cudjoe Key, just 20 minutes from Key West, offering a peaceful retreat in the heart of the Florida Keys. This charming cottage is part of the Venture Out community, providing access to a range of amenities and activities.
The cottage features two bedrooms, one bathroom, and can accommodate up to six guests. Enjoy the spacious backyard with its coconut palms, large BBQ, and outdoor seating, perfect for relaxing and soaking up the tropical atmosphere.

Top-Rated Oceanfront Vacation Rentals in Cudjoe Key, FL

These seaside vacation rentals in Cudjoe Key, FL provide an excellent base for exploring the coast. Browse top local properties and plan your beach-town trip.

Vo Community 501 Midrise 2bd/1.5ba Large Open Deck - Cudjoe Key, FL
9.3 126 reviews
Cudjoe Key, FL
10/14 – 10/20
$221/nighttotal: $1326 (6 )

Vo Community 501 Midrise 2bd/1.5ba Large Open Deck

1 2
apartment , Cudjoe Key
Island Oasis ~ Your Paradise Awaits! - Cudjoe Key, FL
9.7 123 reviews
Cudjoe Key, FL
10/14 – 10/20
$313/nighttotal: $1878 (6 )

Island Oasis ~ Your Paradise Awaits!

2 2
apartment , Cudjoe Key
Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West - Cudjoe Key, FL
8.8 96 reviews
Cudjoe Key, FL
06/18 – 06/29
$254/nighttotal: $2794 (11 )

Old Florida Style, Dockage, Swimming Pool (Shared), Just 20 Miles From Key West

2 2
cottage , Cudjoe Key
Enjoy Caribbean Weather In The Usa. Openings April 2026 - Cudjoe Key, FL
9.4 142 reviews
Cudjoe Key, FL
06/18 – 06/29
$255/nighttotal: $2805 (11 )

Enjoy Caribbean Weather In The Usa. Openings April 2026

2 2
apartment , Cudjoe Key

Discover 5-Star Vacation Rentals in Cudjoe Key, FL

Refined interiors and prime locations make these luxury waterfront vacation rentals in Cudjoe Key, FL the ideal choice for your stay.

Quaint Cottage, Pool, Dockage Just Minutes To Key West! - Cudjoe Key, FL
9.1 323 reviews
Cudjoe Key, FL
10/14 – 10/20
$321/nighttotal: $1926 (6 )

Quaint Cottage, Pool, Dockage Just Minutes To Key West!

2 2
cottage , Cudjoe Key

Best Vacation Rentals with a Steam Room in Cudjoe Key, FL

Maximize your recovery with an on-site sauna, a standard feature at these premier Cudjoe Key, FL vacation rentals.

Oceania... Water Front Cottage Retreat ~ - Cudjoe Key, FL
9.4 227 reviews
Cudjoe Key, FL
10/14 – 10/20
$437/nighttotal: $2622 (6 )

Oceania... Water Front Cottage Retreat ~

2 2
house , Cudjoe Key
Keys House - Venture Out Lot 220 - Cudjoe Key, FL
9.8 16 reviews
Cudjoe Key, FL
10/14 – 10/20
$507/nighttotal: $3042 (6 )

Keys House - Venture Out Lot 220

2 2
apartment , Cudjoe Key
Tides & Tranquility - Venture Out Unit 053 - Cudjoe Key, FL
10 1 review
Cudjoe Key, FL
06/18 – 06/29
$545/nighttotal: $5995 (11 )

Tides & Tranquility - Venture Out Unit 053

2 2
apartment , Cudjoe Key
©2026 cozycozy.com