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
Sep 22 - Sep 23
Tomorrow
Sep 23 - Sep 24
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

Our top choices for Cudjoe Key hotels with a pool

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$351 nightly
$392 total
Sep 27 - Sep 28
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$373 nightly
$416 total
Sep 28 - Sep 29
Total with taxes and fees
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

3. 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
$409 nightly
$454 total
Sep 23 - Sep 24
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$523 nightly
$580 total
Sep 23 - Sep 24
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
$372 nightly
$413 total
Oct 1 - Oct 2
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

6. 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
$427 nightly
$475 total
Sep 23 - Sep 24
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
$457 nightly
$507 total
Sep 23 - Sep 24
Total with taxes and fees
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

8. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
$468 nightly
$520 total
Sep 23 - Sep 24
Total with taxes and fees
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

9. Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
$481 nightly
$534 total
Sep 23 - Sep 24
Total with taxes and fees
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views

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
$474 nightly
$526 total
Sep 23 - Sep 24
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

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent
"Tyrone was extremely helpful with any need that came up. Even when it was not his responsibility, he made sure we were taken care of"
Benjamin Neil 3-night trip
Posted 2 hours ago
DoubleTree Resort by Hilton Grand Key - Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Me encantó la verdad muy limpio trankilo y para ir en familia y con niños lo recomiendo mucho gracias"
Suany 2-night trip
Posted 1 day ago
Hampton Inn Key West FL
Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Comfortable beds"
Paul 3-night trip
Posted 1 day ago
Beachside Resort & Residences
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

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

10/10 Excellent
"Nice place"
Travis 2-night trip
Posted 1 day ago
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Ibis Bay Beach Resort

Ibis Bay Beach Resort

8/10 Good
"Great"
Sergio 2-night trip
Posted 1 day ago
Ibis Bay Beach Resort
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

10/10 Excellent
"This was our second time staying at The Perry and this time we brought friends. The location on the marina is really nice and there are restaurants nearby, like Roostica! We did notice from our 1st stay that the rooms are needing a little TLC regarding maintenance and repairs. Nothing serious, just an observation. BONUS they have an hourly shuttle to/from Key West! We will stay here again!"
Jamie 1-night trip
Posted 1 day ago
The Perry Hotel & Marina Key West
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

10/10 Excellent
"Great place to stay with the family"
Rachel 1-night trip
Posted 2 days ago
Hyatt Vacation Club at Beach House, Key West
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Nice and comfortable"
Erick 2-night trip
Posted 2 days ago
Hilton Key West Resort & Marina
Parmer's Resort

Parmer's Resort

10/10 Excellent
"Wonderful experience! We could walk out of our room to enjoy the water. Nice amenities too! Kayaks and more available, excellent breakfast every morning, way better than the standard breakfast. We would definitely stay there again."
Keith 5-night trip
Posted 2 days ago
Parmer's Resort

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