The Best Cudjoe Key Hotels with Pools from $276 - Hotels with indoor pools in Cudjoe Key, FL

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

Upfront pricing
Our total price for your stay includes taxes and fees
Treat yourself
Save 10% or more on over 100,000 hotels worldwide with Member Prices
Learn about One Key
Be picky
Search almost a million properties worldwide

Check availability on Cudjoe Key Hotels with a Pool

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Cudjoe Key hotels with a pool

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

Cudjoe Key

$460 nightly

$511 total

Sep 4 - Sep 5

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

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

Cudjoe Key

$450 nightly

$499 total

Aug 29 - Aug 30

Total with taxes and fees

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

Cudjoe Key

$520 nightly

$577 total

Aug 25 - Aug 26

Total with taxes and fees

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

Cudjoe Key

$512 nightly

$568 total

Aug 25 - Aug 26

Total with taxes and fees

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

Cudjoe Key

$514 nightly

$571 total

Sep 1 - Sep 2

Total with taxes and fees

6. Seabreeze Escape WF RV Lot 489

Cudjoe Key

$257 nightly

$276 total

Aug 25 - Aug 26

Total with taxes and fees

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

Cudjoe Key

$518 nightly

$575 total

Aug 25 - Aug 26

Total with taxes and fees

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

Cudjoe Key

$549 nightly

$608 total

Aug 25 - Aug 26

Total with taxes and fees

View all properties

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

Hilton Key West Resort & Marina

8/10 Good

"Good: Staff was extremely nice and helpful, the concierge knows everything, the property itself is very nice and the marina is fairly scenic. Beds were comfortable, the A/C goes down to 67 and felt great, the pools are bathwater warm, and the balcony was cozy. Having a shuttle was helpful to get downtown (only has one stop though at the furthest end of town from the Southernmost Point of the US marker - a mile or so away). There's a small gym you can use, and the Tiki Hut has some fun stuff going on (plastic hatchet throwing, shell decorating, pay as you go canoe experiences). The on-site Yellow Fin restaurant is excellent. Bad: Bathroom had no lock on the door, surprise fees for parking and "resort fee" total maybe $70 extra per night (might be mentioned but I didn't notice). Breakfast in the package deal is only free for 2 people per day though (?), leaving us a $40 bill + tip for every breakfast. One whole building is currently undergoing upgrades, so drill, hammer noises, etc, plus big blue tarps all over it."

DoubleTree Resort by Hilton Grand Key - Key West

8/10 Good

"Joe at the front desk was very helpful. We did have a few issues with housekeeping and being able to get into our room. On four separate occasions, we had to come and have someone readjust the lock on our door because our keys did not work. We did enjoy the complementary coffee each morning."

Beachside Resort & Residences

10/10 Excellent

"Me gustó mucho y lo recomiendo muy buena atención y muy limpio"

Parrot Key Hotel & Villas

10/10 Excellent

"The rooms was spacious and immaculate. Check in was very pleasant, we were greeted with mimosas by the staff. The pool and restaurant were amazing as well. Centralized location just minutes form restaurants and activities."

Hampton Inn Key West FL

10/10 Excellent

"outdoor pool"

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent

"Entire stay was fabulous"

Hyatt Vacation Club at Windward Pointe, Key West

8/10 Good

"So we have stayed here both times coming to Key West. The staff is outstanding and very nice from check in.. to check out. I will say that when you purchase through Expedia make sure you still have enough to pay for the resort fees and tax... they are NOT included."

The Perry Hotel & Marina Key West

10/10 Excellent

"very good better than hotel on key west main island"

Fairfield Inn and Suites by Marriott Key West

10/10 Excellent

"Small but clean room, staff was ok. Breakfast was eggs and biscuit which was ok."

Explore a world of travel with Expedia

Lodging

Room 1

Upfront pricing

Treat yourself

Be picky

Check availability on Cudjoe Key Hotels with a Pool

Our top choices for Cudjoe Key hotels with a pool

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

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

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

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