Holiday rentals in Cudjoe Key

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Cudjoe Key

Guests agree: these stays are highly rated for location, cleanliness and more.

Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 130 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

28 Dec – 4 Jan

£660 per night
Guest favourite

Home in Cudjoe Key

4.94 out of 5 average rating, 18 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!

7–14 Jun

£300 per night
Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 122 reviews

Ocean View 2/2 on Canal

Hurricane Ian did no damage This is a non-smoking, no pets, canal front home with a 35' sea wall. Ocean views from either deck. Vaulted great room. Fully equipped kitchen and linens with two private bed/bath suites offering privacy. The resort is gated and secure with plenty of amenities: a small tiki beach, marina, large pool, hot tub, pickle ball, tennis,laundry and general store. One time $113.00 resort fee Required to book: 1. verified identity 2. have positive reviews on AIrbnb

25 Jun – 2 Jul

£367 per night

Popular amenities for Cudjoe Key holiday rentals

Stay near Cudjoe Key's top sights

Sugarloaf Key / Key West KOA Holiday3 locals recommend
Mangrove Mama's21 locals recommend
Square Grouper Bar and Grill47 locals recommend
My New Joint27 locals recommend
Cudjoe Sales Fishermen's Warehouse4 locals recommend
Fanci Seafood3 locals recommend

Other great holiday rentals in Cudjoe Key

Guest favourite

Home in Cudjoe Key

5.0 out of 5 average rating, 18 reviews

Paradise in Cudjoe! Perfect Family Home!

10–17 Nov

£362 per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 24 reviews

Keys Island Villa - Venture Out Home 354

19–26 Dec

£451 per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

28 Sept – 5 Oct

£664 per night
Guest favourite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 74 reviews

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

24 Feb – 3 Mar

£751 per night
Superhost

Home in Cudjoe Key

4.95 out of 5 average rating, 22 reviews

Cozy 2 br/2 bath home in Cudjoe

22–29 Nov

£242 per night
Guest favourite

Holiday home in Cudjoe Key

5.0 out of 5 average rating, 30 reviews

Beautiful Cottage & Amenities in Gated Community

23–30 Aug

£325 per night
Superhost

Home in Cudjoe Key

4.86 out of 5 average rating, 7 reviews

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

30 Nov – 7 Dec

£331 per night
Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 67 reviews

Tree Top Paradise

5–12 Nov

£265 per night
Superhost

Home in Upper Sugarloaf Key

4.86 out of 5 average rating, 43 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

6–13 Aug

£876 per night
Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 32 reviews

Keys getaway

19–26 Jun

£301 per night
Superhost

Cottage in Cudjoe Key

4.94 out of 5 average rating, 52 reviews

Turtle Cove Views @ Venture Out - Waterfront

25 Feb – 4 Mar

£877 per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 18 reviews

Little gem in a safe resort with amenities

9–16 Jul

£262 per night

Quick stats about holiday rentals in Cudjoe Key

Total rentals

190 properties

Rentals with a pool

140 properties have a pool

Pet-friendly rentals

80 properties allow pets

Family-friendly rentals

160 properties are a good fit for families

Total number of reviews

3.7K reviews

Nightly prices starting at

£71 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Cudjoe Key