The Best Cudjoe Key Hotels with Pools from $236 - Hotels with indoor pools in Cudjoe Key, FL

A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

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Our top choices for Cudjoe Key hotels with a pool

A marina with boats, a dock, and a white building with a balcony.

A spacious living area with a wooden ceiling, a ceiling fan, a TV, a glass coffee table, a sofa, a chair, and a kitchen area with a refrigerator and bar stools.

A covered balcony with a table and chairs, a grill, and a boat docked nearby.

A kitchen with white cabinets, stainless steel appliances, and a wooden ceiling.

1. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

$366 nightly

$407 total

Sep 14 - Sep 15

Total with taxes and fees

A beach with a thatched-roof hut, palm trees, and a pebbled walkway leading to the water.

A balcony with a view of neighboring houses, a street, and a clear sky.

A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

A marina with RVs docked along a waterway, surrounded by palm trees and buildings.

2. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

$351 nightly

$392 total

Sep 16 - Sep 17

Total with taxes and fees

3. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key

$494 nightly

$548 total

Sep 14 - Sep 15

Total with taxes and fees

A kitchen with a stainless steel refrigerator, a dining table with chairs, and a view of the street through a window.

A covered outdoor area with wicker furniture and string lights.

4. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key

$511 nightly

$568 total

Sep 14 - Sep 15

Total with taxes and fees

A resort with a swimming pool, beach area, and marina.

A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

A coastal residential area with houses, a marina, and a flag.

5. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Cudjoe Key

$457 nightly

$508 total

Oct 1 - Oct 2

Total with taxes and fees

A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

6. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Cudjoe Key

$553 nightly

$614 total

Sep 14 - Sep 15

Total with taxes and fees

A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

A compact kitchen with white cabinets, a refrigerator, a stove, and a dining area with a table and chairs.

A bedroom with a bed, a ceiling fan, a window with curtains, and a framed picture on the wall.

A living room with a television displaying a show, a ceiling fan, and a window with blinds.

7. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Cudjoe Key

$522 nightly

$579 total

Sep 14 - Sep 15

Total with taxes and fees

8. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Cudjoe Key

$523 nightly

$581 total

Sep 14 - Sep 15

Total with taxes and fees

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Choose what matters most at hotels with a pool in Cudjoe Key

Breakfast included

4 stars

5 stars

Hot tub

Spa

Top Cudjoe Key Hotel Reviews

Beachside Resort & Residences

10/10 Excellent

"Room was excellent. Beachfront that led right up to pool area definitely stay here again its a 10 15 min scooter drive to Duval street but we'll worth to get out of the. Craziness and chill"

Blue Flamingo Resort Key West

8/10 Good

"The room was clean but small. It was hard for all of my family to move around in it. The cleaning staff was not friendly. The pool was clean but really warm. The breakfast that you could purchase was to expensive. $20 for an omelet is to much."

Hyatt Vacation Club at Beach House, Key West

8/10 Good

"Decent room"

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"Beautiful property and rooms!!"

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Good"

Hampton Inn Key West FL

10/10 Excellent

"What a wonderful stay! All of the staff were personable and helpful- I would even say the front desk and concierge were exceptional! Room was a great size and clean, the grounds are well-maintained, and it is in a convenient location with frequent shuttle service from the hotel (close) to Duval St. While it’s not directly on the beach, there are nearby beaches 1+ miles away (the Gulf beaches are a shuttle ride away). Lots of activities nearby, you can walk/run along the oceanfront, and can enjoy the beautiful pool and Tiki Hut onsite. I am looking forward to returning!"

Parmer's Resort

10/10 Excellent

"Excellent resort, clean. Beautiful views, very friendly staff ♥️"

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Our top choices for Cudjoe Key hotels with a pool

1. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

2. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

3. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

4. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

5. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

6. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

7. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

8. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

9. Venture Out RV lot 223

10. Seabreeze Escape WF RV Lot 489

Choose what matters most at hotels with a pool in Cudjoe Key