Vacation Rentals with Pool in Cudjoe Key

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Filtering by: Swimming pool

57 vacation rentals

(15) Very Good 

28

Family Retreat ocean front home with private pool

Florida Keys / Cudjoe Key

Cudjoe Key house

6 18 7 nights min

  • 6 bedrooms
  • sleeps 18
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool

Price per night from

$571

Price per night from

$571

(1) Excellent 

12

Family Friendly 2 Bedroom 1 Bath, 32' Seawall, 4 Bikes, 2 Kayaks and padl board

Florida Keys / Cudjoe Key

Cudjoe Key caravan/mobile home

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$136

Price per night from

$136

13

Paradise on Cudjoe Bay

Florida Keys / Cudjoe Key

Cudjoe Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$271

Responds fast!
avg. 2 hours 23 minutes

Price per night from

$271

(12) Excellent 

24

Fandango

Florida Keys / Cudjoe Key

Cudjoe Key house

5 14 7 nights min

  • 5 bedrooms
  • sleeps 14
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool

Price per night from

$572

Price per night from

$572

(10) Excellent 

24

Tropical Paradise Oceanfront Home with Pool

Florida Keys / Cudjoe Key

Cudjoe Key house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 13 mi
  • Swimming pool
“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The
…see more

Price per night from

$401

Price per night from

$401

(2) Excellent 

22

Oksana's Tropical Beach Oasis

Florida Keys / Cudjoe Key

Cudjoe Key house

5 14 7 nights min

  • 5 bedrooms
  • sleeps 14
  • 7 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child Friendly

Price per night from

$600

Price per night from

$600

(2) Excellent 

24

Blue Palms Retreat (formerly known as Heron's Roost)

Florida Keys / Cudjoe Key

Cudjoe Key house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child Friendly

Price per night from

$358

Price per night from

$358

(2) Very Good 

29

Tropical Blue Adventure Waterfront at Venture Out

Florida Keys / Cudjoe Key

Cudjoe Key house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool

Price per night from

$201

Price per night from

$201

Great rentals within 20 miles that match your search

Distance approx 19.22 km from Cudjoe Key

(19) Excellent 

26

Spectacular Atlantic Ocean View Condo (MONTHLY)

Florida Keys / Key West

Key West apartment

2 6 28 nights min

  • 2 bedrooms
  • sleeps 6
  • 28 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Amazing Views And A Great Condo” My wife and I stayed here on our honeymoon and were absolutely 100% pleased with the condo. I have to honestly say it was the nicest condo either of us have stayed in. The view was amazing and the patio was very tranqu
…see more

Price per night from

$136

Price per night from

$136

Distance approx 0.1 km from Cudjoe Key

(1) Excellent 

20

Paradise n Summerland Key Cove

Lower Keys / Summerland Key

Summerland Key house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$151

Price per night from

$151

Distance approx 0.1 km from Cudjoe Key

(2) Very Good 

15

Island Living

Lower Keys / Summerland Key

Summerland Key house

3 8 28 nights min

  • 3 bedrooms
  • sleeps 8
  • 28 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Price per night from

$226

Price per night from

$226

Distance approx 19.76 km from Cudjoe Key

44

Bed, Breakfast & Beyond Sailing in Key West

Florida Keys / Key West

Key West yacht

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

Price per night from

$701

Price per night from

$701

Distance approx 19.23 km from Cudjoe Key

(49) Very Good 

291

Real World MTV House Key West

Florida Keys / Key West

Key West house

10 22 min stay varies

  • 10 bedrooms
  • sleeps 22
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals
…see more

Price per night from

$1,802

Responds fast!
avg. 1 hour 52 minutes

Price per night from

$1,802

Distance approx 19.75 km from Cudjoe Key

(1) Excellent 

24

Isle Of View II

Florida Keys / Key West

Key West boathouse

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 6 mi
  • Swimming pool
  • Child Friendly

Price per night from

$174

Responds fast!
avg. 2 hours 38 minutes

Price per night from

$174

Distance approx 19.06 km from Cudjoe Key

(1) Excellent 

9

Key West Living-Oceanside Catamaran Wind Spirit

Florida Keys / Key West

Key West yacht

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$320

Price per night from

$320

Distance approx 3.58 km from Cudjoe Key

(1) Excellent 

13

florida keys vacation rental

Lower Keys / Little Torch Key

Little Torch Key house

3 10 5 nights min

  • 3 bedrooms
  • sleeps 10
  • 5 nights min
  • Nearest beach 24 mi
  • Swimming pool
  • Child Friendly

Price per night from

$700

Price per night from

$700

Distance approx 0.1 km from Cudjoe Key

19

Gone Fishing

Lower Keys / Summerland Key

Summerland Key house

3 6 28 nights min

  • 3 bedrooms
  • sleeps 6
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$211

Price per night from

$211

Distance approx 3.49 km from Cudjoe Key

(1) Excellent 

18

Canal Front Home with Seawall & Kayaks

Lower Keys / Little Torch Key

Little Torch Key house

3 7 28 nights min

  • 3 bedrooms
  • sleeps 7
  • 28 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child Friendly

Price per night from

$216

Price per night from

$216

Distance approx 19.54 km from Cudjoe Key

(2) Excellent 

15

Coral Hammock - Comfortable 3 Bedroom Home

Florida Keys / Key West

Key West house

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$320

Responds fast!
avg. 1 hour 32 minutes

Price per night from

$320

Distance approx 19.08 km from Cudjoe Key

26

Key West Harbour Oceanfront Suites #2

Florida Keys / Key West

Key West apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

Distance approx 19.06 km from Cudjoe Key

(1) Excellent 

25

Key West Harbour Oceanfront Suites #3

Florida Keys / Key West

Key West apartment

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$200

Price per night from

$200

Distance approx 19.55 km from Cudjoe Key

(1) Excellent 

12

Comfy Family Home in a Gorgeous Gated Community

Florida Keys / Key West

Key West townhouse

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$279

Responds fast!
avg. 32 minutes

Price per night from

$279

Distance approx 19.41 km from Cudjoe Key

23

70 foot Half million dollar yacht key west

Florida Keys / Stock Island

Stock Island boathouse

4 7 3 nights min

  • 4 bedrooms
  • sleeps 7
  • 3 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child Friendly

Price per night from

$301

Price per night from

$301

Distance approx 19.54 km from Cudjoe Key

(67) Very Good 

30

Tee by the Sea - NO DAMAGE FROM HURRICANE IRMA , Plus 7 Bikes FREE

Florida Keys / Key West

Key West apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
“Absolutely Perfect!!!” I chose this place to rent because it looked nice and it was affordable. I knew going in that it was not located on the Key West island, which was fine considering the condo came with bikes you could ride onto the island...What
…see more

Price per night from

$241

Responds fast!
avg. 2 hours 26 minutes

Price per night from

$241

Distance approx 0.1 km from Cudjoe Key

(1) Excellent 

51

Oceanfront House

Lower Keys / Summerland Key

Summerland Key house

3 8 30 nights min

  • 3 bedrooms
  • sleeps 8
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$334

Responds fast!
avg. 3 hours 43 minutes

Price per night from

$334

Distance approx 5.82 km from Cudjoe Key

28

Florida Keys Fisherman and Divers Paradise

Florida Keys / Big Pine Key

Big Pine Key house

4 12 30 nights min

  • 4 bedrooms
  • sleeps 12
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$251

Price per night from

$251

Distance approx 2.05 km from Cudjoe Key Show on Map

17

Paradise Palms

Lower Keys / Summerland Key

Summerland Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$149

Price per night from

$149

Distance approx 19.06 km from Cudjoe Key

(1) Excellent 

17

DISCOUNTED! 45' Luxury Yacht & Other Boats

Florida Keys / Key West

Key West yacht

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$201

Price per night from

$201

Distance approx 7.52 km from Cudjoe Key

12

Private beach estate. Gated, tropical peace and quiet. Dock.

Florida Keys / Key West

Key West house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$466

Price per night from

$466

Distance approx 7.63 km from Cudjoe Key

9

Key's only real beach home. Dock and pool.

Florida Keys / Key West

Key West house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$344

Price per night from

$344

Distance approx 7.85 km from Cudjoe Key

11

The Key's only real beach house Dock and pool

Florida Keys / Key West

Key West house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$395

Price per night from

$395

Distance approx 6.91 km from Cudjoe Key

8

Key's only real beach home.Gated, private, dock,pool

Florida Keys / Key West

Key West house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$537

Price per night from

$537

Distance approx 18.99 km from Cudjoe Key

(1) Excellent 

19

DISCOUNTED! 45' Luxury Yacht and Other Boats

Florida Keys / Key West

Key West yacht

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$201

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$201

Distance approx 6.87 km from Cudjoe Key

(4) Excellent 

11

Key West's only Real Beach House

Florida Keys / Key West

Key West guest house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Ask about children

Price per night from

$394

Price per night from

$394

Distance approx 7.05 km from Cudjoe Key

26

Private beach estate,gated,dock,and pool.

Florida Keys / Key West

Key West house

5 10 28 nights min

  • 5 bedrooms
  • sleeps 10
  • 28 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$743

Price per night from

$743

Distance approx 19.76 km from Cudjoe Key

(32) Excellent 

28

LAST MINUTE DISCOUNT! 48' Sailing Yacht. Other Yachts & Boats Available!

Florida Keys / Key West

Key West houseboat

4 10 2 nights min

  • 4 bedrooms
  • sleeps 10
  • 2 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$401

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$401

Distance approx 19.72 km from Cudjoe Key

16

SPECIAL OFFER! Like New! Sailing Yacht

Florida Keys / Stock Island

Stock Island yacht

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 2 mi
  • Swimming pool
  • Child Friendly

Price per night from

$301

Responds fast!
avg. 2 hours 11 minutes

Price per night from

$301

Distance approx 6.85 km from Cudjoe Key

16

Private beach estate.Dock and pool.

Florida Keys / Key West

Key West house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child Friendly

Price per night from

$283

Price per night from

$283