Best Vacation Homes in Cudjoe Key
House
8.6(21 Reviews)
2 Bedrooms
2 Baths
6 Guests
864 ft²
Oceanfront
Hot Tub
Pool
Ocean View
£196/Night
7 Nights - £1,372
Villa
10.0(4 Reviews)
4 Bedrooms
2 Baths
10 Guests
2798.62 ft²
Private Beach- Oceanfront
- Hot Tub
Fireplace/Heating
£604/Night
7 Nights - £4,227
Villa
10.0(2 Reviews)
1 Bedroom
1 Bath
Private Pool- Oceanfront
- Hot Tub
- Pool
£817/Night
7 Nights - £5,717
New
House
3 Bedrooms
2 Baths
6 Guests
816 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£646/Night
7 Nights - £4,522
House
10.0(1 Review)
1 Bedroom
2 Baths
4 Guests
861.11 ft²
- Oceanfront
- Hot Tub
Spa- Pool
£353/Night
7 Nights - £2,469
New
House
3 Bedrooms
2 Baths
6 Guests
828 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£474/Night
7 Nights - £3,320
New
RV Rental
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£152/Night
7 Nights - £1,066
House
2 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Ocean View
Balcony/Terrace
View
£145/Night
7 Nights - £1,018
Cudjoe Key Luxury Rentals
House
9.6(61 Reviews)
5 Bedrooms
2 Baths
15 Guests
3001 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
£1,598/Night
7 Nights - £11,184
Villa
4 Bedrooms
2 Baths
10 Guests
1905.21 ft²
Pet Friendly
Internet
Child Friendly
Security/Safety
£892/Night
7 Nights - £6,242
House
4 Bedrooms
2 Baths
10 Guests
3196.88 ft²
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
£758/Night
7 Nights - £5,308
House
10.0(6 Reviews)
3 Bedrooms
3 Baths
8 Guests
2500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£758/Night
7 Nights - £5,307
Villa
9.2(16 Reviews)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Pool
£676/Night
7 Nights - £4,733
Villa
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
1905 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£672/Night
7 Nights - £4,707
House
2 Bedrooms
3 Baths
6 Guests
- Pool
- Balcony/Terrace
Kitchen
Parking
£657/Night
7 Nights - £4,598
House
8.8(14 Reviews)
2 Bedrooms
2 Baths
4 Guests
865 ft²
- Hot Tub
- Pool
- Balcony/Terrace
- Pet Friendly
£649/Night
7 Nights - £4,544
Cudjoe Key Pet Friendly Vacation Rentals
RV Rental
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£92/Night
7 Nights - £645
House
10.0(1 Review)
2 Bedrooms
2 Baths
6 Guests
850.35 ft²
- Hot Tub
- Spa
- Pool
- Pet Friendly
£316/Night
7 Nights - £2,212
House
10.0(12 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£331/Night
7 Nights - £2,319
Resort
9.0(3 Reviews)
1 Bath
4 Guests
721.18 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Spa
£200/Night
7 Nights - £1,403
House
10.0(7 Reviews)
3 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£166/Night
7 Nights - £1,165
House
10.0(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
864 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£314/Night
7 Nights - £2,200
House
10.0(5 Reviews)
2 Bedrooms
2 Baths
6 Guests
850 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£263/Night
7 Nights - £1,841
House
10.0(3 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
£483/Night
7 Nights - £3,381
Cudjoe Key Large Vacation Homes
Villa
10.0(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
850 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£450/Night
7 Nights - £3,152
Villa
7.8(19 Reviews)
2 Bedrooms
2 Baths
6 Guests
753.47 ft²
- Oceanfront
- Hot Tub
- Pool
- Ocean View
£338/Night
7 Nights - £2,366
House
2 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
£136/Night
7 Nights - £953
Villa
1.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
3196.88 ft²
- Private Beach
- Oceanfront
- Hot Tub
- Spa
£614/Night
7 Nights - £4,300
House
10.0(27 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
£300/Night
7 Nights - £2,101
House
10.0(1 Review)
4 Bedrooms
3 Baths
10 Guests
3200 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£488/Night
7 Nights - £3,416
House
10.0(1 Review)
4 Bedrooms
2 Baths
14 Guests
1460 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
£370/Night
7 Nights - £2,592
House
Fandango - private pool This is a pet friendly home. A pet fee and approval of your pet is required.
9.8(88 Reviews)
5 Bedrooms
3 Baths
12 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
£617/Night
7 Nights - £4,320
Why Choose Rent By Owner for your Cudjoe Key Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Cudjoe Key Vacation Rentals
Where are the best neighborhoods to stay in Cudjoe Key?
When choosing where to stay in Cudjoe Key, Florida, you’ll find a variety of neighborhoods that offer the perfect setting for your getaway. The area features peaceful residential communities and scenic waterfront areas, ideal for those seeking relaxation or adventure on the Gulf Coast. Whether you're looking for a quiet retreat close to nature or a lively spot with convenient access to local amenities, Cudjoe Key's neighborhoods provide a range of options to enhance your vacation experience. Booking through trustworthy vacation rentals in this region ensures a seamless stay in one of Florida’s most charming coastal destinations.
Cudjoe Gardens
This neighborhood offers a tranquil setting where you can enjoy the peaceful surroundings while staying close to the natural beauty of the region. Finding a comfortable property here provides easy access to the serene waters and scenic views that make this area special.
View 625+ Rentals in Cudjoe GardensCutthroat Harbor Estates
Located nearby, this community is ideal for those seeking a quiet retreat with convenient access to waterfront activities. Your choice of a vacation rental here ensures a relaxed stay surrounded by the charming coastal landscape.
View 69+ Rentals in Cutthroat Harbor EstatesBest Times to Visit Cudjoe Key
When should you plan your Vacation Rentals stay?
Choosing the right time to visit this destination can enhance your experience, as the area's mild winters and warm summer months offer ideal conditions for enjoying your stay in Florida.
Peak Season Highlights
Winter (December to February)
During the winter months, this destination experiences its busiest period as visitors seek warm escapes and sun-filled days in the region.
Average Temperature Daytime: 75°F to 80°F - Nighttime: 65°F to 70°F
Spring Break (March to April)
Spring break attracts many travelers looking for a lively atmosphere and ideal weather, making it a peak time to stay in vacation rentals here.
Average Temperature Daytime: 78°F to 82°F - Nighttime: 68°F to 72°F
Off-Season Highlights
Summer (June to August)
The summer months see a slight decline in visitors, offering quieter access to the region’s natural beauty and more budget-friendly rental options.
Average Temperature Daytime: 85°F to 89°F - Nighttime: 75°F to 79°F
Fall (September to November)
Autumn brings fewer tourists, making it an excellent time to enjoy the region’s serenity while accessing attractive rates on vacation rentals.
Average Temperature Daytime: 80°F to 84°F - Nighttime: 70°F to 74°F
Weekly Weather Forecast for Cudjoe Key
How to Book Your Cudjoe Key Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Cudjoe Key
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor swimming pool to relax after a day of exploring the region.
- Take advantage of spacious patios or decks with outdoor furniture for al fresco dining.
- Benefit from direct access to nearby beaches or waterfront areas for sunbathing and water activities.
- Make use of outdoor grills or barbecue stations for memorable cookouts with family and friends.
- Utilize well-maintained landscaped gardens or yards for outdoor recreation or gatherings.
- Relax in shaded gazebo or cabana areas designed for comfort and leisure during your stay.
- Find convenient parking spaces with designated outdoor parking options for easy access during your trip.
Top Attractions Around Cudjoe Key
What attractions are nearby?
In this destination, you can enjoy a variety of outdoor activities such as fishing, boating, and snorkeling, all just moments from your vacation rental in the region.
Family Activities
- Coral Reef Park: Spend a day outdoors at this family-friendly park, offering playgrounds, picnic areas, and opportunities for water activities along the scenic shoreline.
- Fishing Charters: Experience the thrill of deep-sea fishing on a charter trip, perfect for families looking to enjoy the region’s abundant marine life.
- Blue Hole: Explore this natural freshwater pond that provides a safe and engaging spot for children to snorkel and observe local aquatic life amidst the area's tranquil environment.
- Kayaking Adventures: Discover the calm waters and mangrove pathways by renting kayaks, offering an exciting way for families to explore the region's rich ecosystem together.
Adult Activities
- Fishing Charters: Embark on a guided fishing trip to experience the rich waters surrounding this island destination, perfect for anglers seeking a memorable day at sea.
- Snorkeling and Diving: Explore the vibrant coral reefs and diverse marine life just off the coast, offering an immersive underwater adventure in this popular region.
- Kayaking and Paddleboarding: Enjoy a peaceful paddle across calm waters and mangroves, ideal for those looking to connect with nature in this tranquil area.
- Wildlife Watching Tours: Join a tour to observe local bird species and marine creatures, providing an engaging experience along the scenic shoreline of the region.
Other Places to Stay in Cudjoe Key, FL
Lower Keys
Cudjoe Gardens
Cutthroat Harbor Estates
Cudjoe Key Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Water Activities: Take advantage of the region’s renowned boating, kayaking, and snorkeling opportunities to fully enjoy the coastal beauty here.
- Plan Your Visit During Off-Peak Seasons: Visiting during less busy times can help you experience a more relaxed atmosphere while securing better rates on your vacation rentals.
- Choose a Prime Location for Your Accommodation: Select a property close to popular beaches or waterfronts to maximize your leisure time and scenic views in this destination.
- Engage with Local Guides and Tours: Participating in guided excursions allows you to uncover hidden gems and gain insider knowledge about the area's natural wonders.
Transportation Options
- Car Rentals: Renting a car is a convenient option for exploring the area and accessing nearby islands with ease.
- Taxi Services: Taxis provide on-demand transportation, making it simple to get around without the hassle of parking.
- Shuttle Services: Shuttle options are available for quick transfers to and from local airports and popular destinations here.
- Public Transportation: Local bus services offer an affordable way to navigate the region without needing your own vehicle.
Local Customs Options
- Seafood Customs: Locals here take pride in their fresh seafood, often enjoying traditional dishes like stone crab and key lime shrimp as part of their daily routines.
- Respect for Marine Life: It is customary to honor the region's marine environment by practicing responsible boating and fishing practices, ensuring the area's natural beauty and biodiversity are preserved.
- Island Hospitality: Visitors are welcomed with a friendly spirit that emphasizes laid-back hospitality, reflecting the relaxed vibe of this coastal destination.
- Community Celebrations: Participating in local festivals and events, especially during holiday seasons, offers a genuine glimpse into the area's vibrant cultural traditions.
Frequently Asked Questions About Cudjoe Key?
1. What are the top vacation rentals in Cudjoe Key?
There are a lot of options in Cudjoe Key. If you plan on staying in the Cudjoe Key area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Cudjoe Key:
- Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
- Luxurious Oceanfront Home on Beach, Pool, Dock, Kayaks, Bikes, Amazing Views!
- White Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Oceanside home, dock,kayaks,bikes,pool,fishing,109
- Blue Home - Receive 400 dollars towards a BOAT RENTAL!
- Oceanside home, dock,kayaks,bikes,pool,fishing,111
- Yellow Home - Receive 400 dollars ntowards a BOAT RENTAL!
- Post Card Point #319 - Ocean Views!
- Latitude Adjustment #598, Canal front-Ocean Views
- Looking for a place to stay?
2. How many vacation rentals have private pools in Cudjoe Key?
There are 72 vacation rentals with private pools near Cudjoe Key. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Cudjoe Key are best for families?
If you are looking for a family-friendly vacation home in Cudjoe Key, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cudjoe Key:
4. How many Rentbyowner vacation rentals are available in Cudjoe Key?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 590 in the Cudjoe Key area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Cudjoe Key.
5. What is the cancellation policy for vacation rentals in this area?
Cancellation policies vary depending on the individual rental listing. To ensure you understand the specific terms, please review the cancellation policy outlined on the property’s page or contact the owner directly before booking.
6. Are there any additional fees I should be aware of when booking a vacation rental?
Additional fees such as cleaning fees, service charges, or security deposits are often specified in the listing details. It's recommended to read the full description and reach out to the property owner if you have questions about extra costs.
7. How do I confirm my reservation in this destination?
Reservations are confirmed once you complete the booking process through the listing page. Some owners may require approval prior to confirmation; always check the detailed instructions and contact them if needed to finalize your stay.
8. What amenities are typically included in vacation rentals here?
Amenities vary by property but generally include essentials like Wi-Fi, kitchen facilities, air conditioning, and parking. For specific amenities, refer to each listing’s detailed description or contact the owner directly for clarification.
9. What should I do if I need to modify or cancel my booking?
Modifications or cancellations should be managed through your booking account or by contacting the property owner directly. Be sure to review the cancellation policy beforehand to understand any penalties or refund procedures applicable in this region.
Cudjoe Key Top Rated Vacation Rentals
House
10.0(234 Reviews)
2 Bedrooms
3 Baths
6 Guests
1200 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
£357/Night
7 Nights - £2,496
House
10.0(211 Reviews)
2 Bedrooms
3 Baths
6 Guests
1200 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£374/Night
7 Nights - £2,616
House
10.0(209 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£429/Night
7 Nights - £3,005
House
10.0(179 Reviews)
2 Bedrooms
3 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£390/Night
7 Nights - £2,733
House
10.0(161 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
£427/Night
7 Nights - £2,988
House
10.0(158 Reviews)
2 Bedrooms
4 Baths
6 Guests
1200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
£409/Night
7 Nights - £2,862
House
10.0(150 Reviews)
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
£336/Night
7 Nights - £2,354
House
10.0(54 Reviews)
2 Bedrooms
2 Baths
4 Guests
864 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
£500/Night
7 Nights - £3,504
