TOP Hotels with Air Conditioning in Cudjoe Key, FL for 2026

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 air conditioning

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

Cudjoe Key

£365

includes taxes & fees

5 Sept - 6 Sept

Coffee/tea maker, fridge, microwave, oven

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

Cudjoe Key

Cheryl V.

£414

includes taxes & fees

1 Sept - 2 Sept

2 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cudjoe Key

James B.

£359

includes taxes & fees

15 Aug - 16 Aug

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

Cudjoe Key

Kiara

£444

includes taxes & fees

17 Aug - 18 Aug

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

Cudjoe Key

David T.

£362

includes taxes & fees

12 Aug - 13 Aug

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

Cudjoe Key

jim b.

£425

includes taxes & fees

1 Sept - 2 Sept

7. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Cudjoe Key

BRIAN S.

£342

includes taxes & fees

11 Aug - 12 Aug

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

Cudjoe Key

Phani U.

£450

includes taxes & fees

17 Aug - 18 Aug

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Top Cudjoe Key Hotel Reviews

The Perry Hotel & Marina Key West

10/10 Excellent

"Excellent all around."

Blue Flamingo Resort Key West

10/10 Excellent

"Everything is absolutely satisfied by me However you can still improve more better I really enjoyed myself"

Hampton Inn Key West FL

8/10 Good

"Loved the place! Room was overlooking the water across A1A. Everyone was very nice. Only issue was it sounded like weird activity in the unit above our room. Heavy things being drug across the floor mainly. The door closures need adjusted so all of them stop slamming shut. Adjusted way too strong. Doors banging often. Other than that, great place! Loved the pool and Cheekie Hut and food service. Breakfast was excellent! Really enjoyed our stay a lot!"

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent

"The property is absolutely STUNNING. Balconies with rocking chairs, table and telescope. Gas grills, lovely infinity pool and hot tub. Close to the airport, over 4 days I heard the planes like 5 or 6 times and that was it. Need to Uber or Cab down to Old Town. Maria was AWESOME, she showed us to our room. Room was extremely clean and beautiful, had everything we needed. It was not ready when we arrived but they secured all.of our luggage so we could go ahead and explore and use the amenities, then delivered the luggage to our room for us!! We had so much fun, delicious drinks at the bar, the Benihana out front is great too!! We will DEFINITELY come back to this property again and again. Also great for handicap access, one of our party is disabled and she had zero problems with the stay. Would give more"

Beachside Resort & Residences

10/10 Excellent

"Clean. Balcony was very good, Beach access."

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent

"Everything was great! I wish they had slips for larger boats 36' +"

Ibis Bay Beach Resort

10/10 Excellent

"Clean room, A/C was great."

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

10/10 Excellent

"The breakfast was fabulous"

Fairfield Inn and Suites by Marriott Key West

8/10 Good

"The pool water wasn't clean, and the restaurant and bar were far from comfortable—the hotel claimed this was due to renovations. I don't know if they always tell guests the same thing, but at the time of our visit, it was very uncomfortable and not a pleasant place to have breakfast."

Frequently asked questions

How much do hotels with air conditioning in Cudjoe Key cost?

Hotels with air conditioning in Cudjoe Key range between £79 and £839 per night. These stays offer the comfort you desire at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Are there any family-friendly hotels with air conditioning in Cudjoe Key?

You bet! Reserve a stay at Looe Key Reef Resort — a 2.5-stars property only a quick drive from downtown Cudjoe Key. This family-friendly hotel with air conditioning also has handy amenities like a nearby beach and housekeeping services. Cudjoe Key has no shortage of family-friendly attractions to visit when the kids are getting restless. Florida Keys Beaches and Sugarloaf Beach guarantee a fun day out for all ages.

Why book your hotel with air conditioning in Cudjoe Key with Expedia?

Travelling should be simple, so if you're in search of hotels with air conditioning at the perfect price, Expedia has got you covered. Keep costs down and check in to an all-inclusive resort with AC, or splurge and book 5-star accommodation to spoil your loved ones.

How can I find cheap hotels with air conditioning in Cudjoe Key?

Expedia can help you easily source cheap hotels with air conditioning in Cudjoe Key. Just select the "air conditioned" box under the amenities filter (on the left of the webpage) to view all stays with this feature. Next, choose your hotel star rating (lower-rated stays are easier on the wallet!) and your budget per night to find the best properties with air conditioning at a terrific price.

Room 1

Change your mind

Treat yourself

Be picky

Check availability on Cudjoe Key Hotels with Air Conditioning

Our top choices for Cudjoe Key hotels with air conditioning

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

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

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

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

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

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

7. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

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

9. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

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