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
20 Sep - 21 Sep
Tomorrow
21 Sep - 22 Sep
Next weekend
25 Sep - 27 Sep
In two weeks
2 Oct - 4 Oct

Our top choices for Summerland Key hotels with a pool

Outdoor pool, open 7:00 AM to 10:00 PM, pool umbrellas, sun loungers
Karaoke room
Lunch and dinner served
Sports bar, pool views, open daily

1. Looe Key Reef Resort

Looe Key Reef Resort
Summerland Key
  • Sun-dappled pool paradise at Looe Key Reef Resort offers snorkeling adventures nearby.
AED 278
AED 313 total
includes taxes & fees
23 Sep - 24 Sep
Looe Key Reef Resort
Dock
Exterior
Suite, 1 Bedroom, Kitchen, Sea Facing | Living area | TV, books, stereo
Private beach, sun loungers, beach umbrellas, beach towels

2. 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.
AED 528
AED 713 total
includes taxes & fees
4 Oct - 5 Oct
Parmer's Resort
Outdoor pool
Property grounds
Exterior
Restaurant

3. Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
  • Dive into paradise at this oceanfront retreat with heated pool, marina access, and tennis courts.
AED 437
AED 492 total
includes taxes & fees
21 Sep - 22 Sep
Sugar Loaf Lodge
Outdoor pool, a heated pool
Exterior
Exterior
Property grounds

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

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
AED 474
AED 1,504 total
includes taxes & fees
27 Sep - 28 Sep
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor pool, a heated pool
Outdoor dining
Exterior
Coffee/tea maker, fridge, microwave, oven

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
AED 474
AED 1,493 total
includes taxes & fees
21 Sep - 22 Sep
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool
Beach
Sport court
Outdoor dining

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
AED 579
AED 1,667 total
includes taxes & fees
21 Sep - 22 Sep
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A heated pool
Dining
Terrace/patio
Beach

7. 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
AED 636
AED 1,743 total
includes taxes & fees
21 Sep - 22 Sep
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior detail
TV
2 bedrooms, WiFi, bed sheets
Shower, hair dryer, towels, soap

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
AED 671
AED 2,130 total
includes taxes & fees
21 Sep - 22 Sep
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Exterior
Property grounds
Property grounds
Terrace/patio

9. Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
AED 551
AED 1,002 total
includes taxes & fees
21 Sep - 22 Sep
Seabreeze Escape WF RV Lot 489
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Choose what matters most at hotels with a pool in Summerland Key

Breakfast included
4 stars
Hot tub
5 stars
Spa

Hotels with pools and hot tubs in Summerland Key

Terrace/patio
Smart TV, table tennis, books
A heated pool
Beach

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
AED 1,446
AED 2,739 total
includes taxes & fees
21 Sep - 22 Sep
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Beach
Terrace/patio
A heated pool
Smart TV, table tennis

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
AED 1,504
AED 3,054 total
includes taxes & fees
21 Sep - 22 Sep
Post Card Point #319 - Ocean Views!
Exterior
2 bedrooms, iron/ironing board, WiFi, bed sheets
Outdoor pool, a heated pool
Coffee/tea maker, fridge, microwave, oven

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
AED 474
AED 1,493 total
includes taxes & fees
21 Sep - 22 Sep
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Outdoor dining
Beach
Exterior
Smart TV, table tennis, books

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views

Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Cudjoe Key
AED 1,446
AED 2,982 total
includes taxes & fees
21 Sep - 22 Sep
Caribbean Blue #517 Oceanfront Retreat with Dock, Pool & Stunning Views
Beach
Marina
A heated pool
Exterior

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
AED 771
AED 1,932 total
includes taxes & fees
21 Sep - 22 Sep
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A heated pool
Exterior
Coffee/tea maker, fridge, microwave, oven
Beach

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
AED 829
AED 1,982 total
includes taxes & fees
21 Sep - 22 Sep
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
A heated pool
Smart TV, table tennis, books
Outdoor dining
Beach

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
AED 771
AED 1,895 total
includes taxes & fees
21 Sep - 22 Sep
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Outdoor dining
Outdoor pool, a heated pool
Interior
Beach towels

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

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
AED 857
AED 1,717 total
includes taxes & fees
21 Sep - 22 Sep
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Exterior
Beach nearby
Marina
A heated pool

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Cudjoe Key
AED 1,523
AED 2,851 total
includes taxes & fees
21 Sep - 22 Sep
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
A heated pool
Beach
Sport court
Outdoor dining

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
AED 579
AED 1,667 total
includes taxes & fees
21 Sep - 22 Sep
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Summerland Key Hotel Reviews

Parmer's Resort

Parmer's Resort

10/10 Excellent
"Excellent resort, clean. Beautiful views, very friendly staff ♥️"
Mireya 1-night trip
Posted 8 days 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 snack bar/deli. Sugarloaf Key RV Resort & Cottages: Provides a private beach, an outdoor pool, and a full-service spa. 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 Pye 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.