We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Cudjoe Key Family & Kid Friendly Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighborhood
89 rentals in Cudjoe Key.
Sort by:
Tripadvisor Sort
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Luxury Home w/ 180-Degree Bay Views, Boat Docks, Pool Table & Huge Deck
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Luxurious Oceanfront Home on Beach, Dock, Heat/Cool Pool, Kayaks, FirePit, Bikes
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
**TIDEWATER VIEWS * VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Beautiful Family-Friendly home, Dock, Heated Pool, near Key West, MM21.5
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
* OCEAN FRONT * PRIVATE 56' DOCK * 5 to 7 night min. * MAXIMUM OCCUPANCY 4 **
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cottage by the Sea 1BD/1BA Boat Dockage Heated Pool
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Venture Out - Waterfront Paradise 2/1, with 35' Dock and open water views!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
REDUCED SPRING RATES! Private Home in Waterfront Community Pool Kayaks Bikes
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Paradise awaits you at Blue Moon!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Save time - get the best Cudjoe Key rentals sent straight to your email!
Casa Del Mar 2 Bedroom Waterfront Getaway - 5 Star Gated Community
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Sparkling Clean & New Turn Key 1Bd/1Ba
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Tropical Getaway in a Fisherman's paradise
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
“Key's Life' Ocean Views, Sunsets and Tropical Breezes Await You!!!”
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Crystal Clear Water Getaway!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Opening available!! Sanitized and ready to go!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
OCEAN FRONT: The Glass House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
WATERFRONT fresh & cozy 2 bedroom 35 sea wall New UV light air purification safe
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Peaceful and Ocean View Estate 15 minutes from Key West
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
VO 173 2 Bed 2 Bath Silt Canal-Front, Ocean View
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Fandango
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Payment Protection
Resort Waterfront Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Comfortable Waterfront Vacation Rental
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Tropical Paradise Oceanfront Home with Pool
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Key Lime Cottage in Cudjoe Key
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Shangri-la in the Keys! Enjoy the water views and a 45' dock space!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Paradise Awaits, Stilt home on Canal for fisherman,or Rest and Relaxation
1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Dolphin House (#386) with beautiful open water views
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Lovely Furnished Home in Oceanfront Community w/Shared Boat Docks, Pool & Beac
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
We know you need a vacation after this year!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Family Retreat-Ocean front home with private pool
6 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Payment Protection
Relaxing and Inviting home in gated community
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PALM TREE PARADISE AT VENTURE OUT+ 4 BIKES, 2 KAYAKS, PATIO, QUEEN & FULL BEDS!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Island Retreat With 35 Foot Dock
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Venture Out #465 2/2 Tropical Getaway on Canal with Open Water View
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
LATITUDE ADJUSTMENT
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Direct Oceanfront - Atlantic Side - Dockage - Swimming Pool - Kayak
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
BIG BLUE waits for you in the sunny Keys
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
WALK TO THE BEACH! Upscale Designer 2Bd/2Ba in Venture Out a Gated Communi
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
OCEANVIEW PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS!
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Night jasmine oceanfront vacation house
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
MAGNIFICENT OCEAN VIEW w/35' of DOCKAGE!! Gated Resort with many activities.
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Brand new 4 bedroom 4 bath home with a beautiful pool and dock near Key West.
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Waterfront Relaxation and Barefoot Sunsets
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Blue Palms Retreat. ocean front w/pool and dock for your boat.
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Dog-friendly resort community home w/ shared pool, hot tub, & tennis court!
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Charming 3bedroom/2bath home in the Florida Keys
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Paradise in the Keys close to oceanfront pool with 35' seawall
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
12