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

Find Hotels with a Pool in Cudjoe Key, FL

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Check availability on Cudjoe Key Hotels with a Pool

Tonight
Aug 24 - Aug 25
Tomorrow
Aug 25 - Aug 26
This weekend
Aug 28 - Aug 30
Next weekend
Sep 4 - Sep 6

Our top choices for Cudjoe Key hotels with a pool

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

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
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

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$450 nightly
$499 total
Aug 29 - Aug 30
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$528 nightly
$586 total
Aug 26 - Aug 27
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe Key
$512 nightly
$568 total
Aug 26 - Aug 27
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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

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

6. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$257 nightly
$276 total
Aug 26 - Aug 27
Total with taxes and fees
Seabreeze Escape WF RV Lot 489

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

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
$518 nightly
$575 total
Aug 26 - Aug 27
Total with taxes and fees
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
$549 nightly
$608 total
Aug 26 - Aug 27
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$473 nightly
$525 total
Aug 26 - Aug 27
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
$560 nightly
$621 total
Aug 26 - Aug 27
Total with taxes and fees
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
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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

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

10/10 Excellent
"Very comfortable, Clean & Roomy. Friendly Staff Pool is Fabulous, with plenty of patio space. A few outdoor activities… shuffle board, beach volleyball & corn hole boards 8 large outdoor gas grills, cleaned daily!!"
Lois 4-night trip
Posted 2 hours ago
Hyatt Vacation Club at Windward Pointe, Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

8/10 Good
"No free parking not on beach"
Robert 5-night trip
Posted 2 hours ago
Hampton Inn Key West FL
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Excelente instalación y servicio, recomendada al 100%,"
Yusbel 2-night trip
Posted 5 hours ago
Blue Flamingo Resort Key West
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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

8/10 Good
"This is a great place for a multi-day stay in Key West. I stayed at the Fairfield which is part of 4 connected hotels. I enjoyed the admission to the Blue Flamingo pool great vibe including its lawn area. 3 of the 4 pools were very warm and the breakfast buffet could be helped by adding more waffle machines which are very popular. Otherwise every went well. Will stay there again."
Reynaldo 2-night trip
Posted 7 hours ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Beautiful resort and location. Having construction and updating while we were there as it recently became a Hilton resort. Love the location and the 2 hours of kayak/ paddle boarding and/or bicycling that was provided at no cost. Air conditioning in unit had issues but they tried to correct while there and it got a little better. Staff was very friendly and attentive. Had issues with the bill and they corrected it and gave me free parking for my trouble. Yellowfin Restaurant was wonderful. Need to improve happy hour as no discount with drinks were a part of it."
Todd 3-night trip
Posted 8 hours ago
Hilton Key West Resort & Marina
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Was clean breakfast was perfect nice little beach was also clean good place"
Roland 1-night trip
Posted 10 hours ago
Ibis Bay Beach Resort
DoubleTree Resort by Hilton Grand Key - Key West

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."
Susan 4-night trip
Posted 1 day ago
DoubleTree Resort by Hilton Grand Key - Key West
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Me gustó mucho y lo recomiendo muy buena atención y muy limpio"
Jose 2-night trip
Posted 1 day ago
Beachside Resort & Residences
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

10/10 Excellent
"Entire stay was fabulous"
Amanda 2-night trip
Posted 1 day ago
Hilton Garden Inn Key West / The Keys Collection

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