A coastal road with a beach on one side and a marina with boats on the other.

Find Hotels with a Pool in Summerland Key, FL

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Check availability on Summerland Key Hotels with a Pool

Tonight
Aug 9 - Aug 10
Tomorrow
Aug 10 - Aug 11
Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23

Our top choices for Summerland Key hotels with a pool

1. Parmer's Resort

Parmer's Resort
Summerland Key
  • Soak up sun and sea at this coastal oasis with a sparkling pool, private beach, and marina.
$148 nightly
$167 total
Aug 10 - Aug 11
Total with taxes and fees
Parmer's Resort

2. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
$100 nightly
$112 total
Sep 2 - Sep 3
Total with taxes and fees
Looe Key Reef Resort

3. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
$119 nightly
$134 total
Aug 16 - Aug 17
Total with taxes and fees
Sugar Loaf Lodge

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

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$391 nightly
$434 total
Aug 15 - Aug 16
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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
$439 nightly
$487 total
Sep 4 - Sep 5
Total with taxes and fees
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

6. 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
$501 nightly
$555 total
Sep 1 - Sep 2
Total with taxes and fees
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
$542 nightly
$601 total
Aug 17 - Aug 18
Total with taxes and fees
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
$391 nightly
$434 total
Aug 12 - Aug 13
Total with taxes and fees
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

9. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
$244 nightly
$262 total
Sep 8 - Sep 9
Total with taxes and fees
Seabreeze Escape WF RV Lot 489

10. 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
$518 nightly
$575 total
Sep 1 - Sep 2
Total with taxes and fees
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
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Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"This place reminds me of visiting the Keys as a kid with my family. Lots of amenities on the property, a little beach area, and a location that's just right. The rooms aren't "fancy", but everything was well maintained, the air conditioning was excellent, and everything was spotless. Sara at the front desk was friendly and helpful! Can't wait to return!"
Brenda 1-night trip
Posted 16 hours ago
Parmer's Resort

Frequently asked questions

What's it like visiting Summerland Key?
If lounging next to a pool is your idea of a great vacation, you may want to consider Summerland Key, which has 27 places to stay with pools. During your visit, you can explore attractions like Florida Keys Beaches, and then kick back and relax poolside at one of the accommodations in Summerland Key that travelers like for their pools.
What are some accommodations with pools in Summerland Key?
Parmer's Resort: Features a private beach, an outdoor pool, and daily. Sugarloaf Key Hotel at KOA Resort: Offers a private beach, an outdoor pool, and a full-service spa. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool, and a snack bar/deli. Sugar Loaf Lodge: Features free self parking, an outdoor pool, and complimentary wireless internet access. Looe Key Reef Resort: Hotel located near Florida Keys Beaches. Offers 2 outdoor tennis courts, an outdoor pool, and free self parking.
How many hotels with pools will I be able to find in Summerland Key?
Expedia's 27 hotels in Summerland Key give you a great choice for your poolside getaway.
What is there to see and do in Summerland Key?
Explore places like Florida Keys Beaches while you're in Summerland Key. Spend some time experiencing the great outdoors at Upper Sugarloaf Key and Venture Key.
When is the best time to book a hotel with a pool in Summerland Key?
Taking into account the local weather in Summerland Key is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. Average annual precipitation for Summerland Key is 35 inches.

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