A sign reading "CUDJOE KEY" by a coastal road with a clear sky and calm sea.

Cudjoe Key Vacation Rentals

Dates

November 2026

8

December 2026

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Check prices for these dates

In two weeks

Nov 20 - Nov 22

In two months

In three months

Jan 29 - Jan 31

In four months

Feb 26 - Feb 28

Map of Cudjoe Key

Our top choices for Cudjoe Key vacation rentals

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

1. Atlantic View Luxury Villa with Pool

Summerland Key

United States

Preetam

P61,531 total

includes taxes & fees

Nov 15 - Nov 16

A wooden deck with a hanging hammock and a view of a green landscape.

2. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

United States

max

P45,565 total

includes taxes & fees

Nov 19 - Nov 20

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

3. Old Wooden Bridge Resort and Marina

Punta Brisa

United States

Jordan

P13,824 total

includes taxes & fees

Dec 4 - Dec 5

A row of floating houses with balconies, connected by walkways, on calm water.

4. Aqua Lodges at Hurricane Hole Marina

Stock Island

United States

Kagni

P18,393 total

includes taxes & fees

Nov 9 - Nov 10

A waterfront property with a large building featuring balconies and a covered area, boats docked in front, and palm trees in the background.

5. Grand Marina Suite by Brightwild Waterfront

Stock Island

United States

Pawel

P42,943 total

includes taxes & fees

Nov 9 - Nov 10

A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

6. The Grenada Suite Pool View Private Balcony

Key West

United States

Luis

P35,076 total

includes taxes & fees

Nov 30 - Dec 1

A poolside area with lounge chairs, a wooden table, and palm trees.

7. The Fairhaven House at Solaire Lunara Bay

Raccoon Key

P154,413 total

includes taxes & fees

Nov 9 - Nov 10

A wooden pedestrian bridge over a water body, surrounded by lush greenery and palm trees.

8. Tortuga Suite Sparkling Pool Hot Tub

Key West

P35,441 total

includes taxes & fees

Dec 1 - Dec 2

A modern kitchen with a long island counter, bar stools, pendant lighting, and large windows.

9. Waterfront Luxury Home - Tidelands House

Raccoon Key

P154,413 total

includes taxes & fees

Nov 9 - Nov 10

A white two-story house with a central archway and a paved driveway.

10. Palmgale House in Key West

Raccoon Key

P132,254 total

includes taxes & fees

Nov 9 - Nov 10

A modern house with a swimming pool, outdoor seating, and palm trees.

11. Floralee House in Key West

Raccoon Key

P142,164 total

includes taxes & fees

Nov 9 - Nov 10

A spacious kitchen with modern appliances, a dining area with a wooden table and chairs, and a view of a lake through large windows.

12. Springtide House by Brightwild Waterfront Pool

Raccoon Key

P105,609 total

includes taxes & fees

Nov 9 - Nov 10

A modern kitchen with a central island, bar stools, and a large window.

13. Brand New Catchlight House With Private Pool

Raccoon Key

P132,254 total

includes taxes & fees

Nov 9 - Nov 10

A spacious kitchen with a large island, white cabinetry, and pendant lighting.

14. Aquaria House by Brightwild Pool Boat Dock

Raccoon Key

P105,609 total

includes taxes & fees

Nov 9 - Nov 10

A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.

15. Suncoast House by Brightwild Pool Boat Dock

Raccoon Key

P116,333 total

includes taxes & fees

Nov 9 - Nov 10

A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.

16. New Waterfront Home - Dreamside House

Raccoon Key

A spacious kitchen with a large island, pendant lighting, and a dining area with a table and chairs.

17. New Windrose House by Brightwild Pool

Raccoon Key

P213,718 total

includes taxes & fees

Nov 21 - Nov 22

A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

18. Spindrift House by Brightwild Huge Pool Dock

Raccoon Key

A modern kitchen with white cabinetry, a marble countertop, and a central island with bar stools.

19. New Altair House by Brightwild Pool Pets

Raccoon Key

P222,812 total

includes taxes & fees

Nov 21 - Nov 22

A spacious kitchen with a marble island, pendant lighting, and a dining area with chairs and a table.

20. New Crestwood House by Brightwild Huge Pool

Raccoon Key

P132,254 total

includes taxes & fees

Nov 9 - Nov 10

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