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Vacation rentals in Cudjoe Bay

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cudjoe Bay

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!

Dec 28 – Jan 4

$660 per night
Guest favorite

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!

Jun 7 – 14

$264 per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

Oct 16 – 23

$102 per night

Popular amenities for Cudjoe Bay vacation rentals

Other great vacation rentals in Cudjoe Bay

Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

Sep 28 – Oct 5

$594 per night
Guest favorite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 74 reviews

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

Feb 24 – Mar 3

$728 per night
Superhost

Home in Upper Sugarloaf Key

4.86 out of 5 average rating, 43 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Aug 6 – 13

$774 per night
Guest favorite

Vacation home in Cudjoe Key

5.0 out of 5 average rating, 30 reviews

Beautiful Cottage & Amenities in Gated Community

Aug 23 – 30

$301 per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 6 reviews

Sailfish Haven

Aug 27 – Sep 3

$265 per night
Superhost

Home in Cudjoe Key

4.95 out of 5 average rating, 22 reviews

Cozy 2 br/2 bath home in Cudjoe

Nov 22 – 29

$231 per night
Superhost

Place to stay in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Keysie Does It @ Cudjoe Key - Home in Waterfront

Sep 9 – 16

$291 per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 37 reviews

Keys Cove

Jan 18 – 25

$332 per night
Superhost

Home in Cudjoe Key

4.82 out of 5 average rating, 67 reviews

Tree Top Paradise

Nov 5 – 12

$241 per night
Superhost

Home in Cudjoe Key

4.81 out of 5 average rating, 32 reviews

Keys getaway

Jun 19 – 26

$290 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

Nov 30 – Dec 7

$321 per night
Guest favorite

Condo in Key West

4.99 out of 5 average rating, 83 reviews

Hidden Beach Duplex, Best Place in Key West

Aug 2 – 9

$608 per night

Destinations to explore

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  3. Florida
  4. Monroe County
  5. Cudjoe Bay