Summerland Key, FL Condos for Rent

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Our top choices for Summerland Key condo rentals

A room with a sofa, a television, a table, and a balcony with a view.

1. The Curaçao | Key West Condo with Pool, Balcony, & Sunset Views

Key West

$424 nightly

Nov 15 - Nov 16

Total with taxes and fees

A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

2. The Grand Cayman | Beautifully Remodeled Key West!

Key West

Matt R.

$428 nightly

Nov 29 - Nov 30

Total with taxes and fees

A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

3. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

Key West

Teri K.

$425 nightly

Nov 10 - Nov 11

Total with taxes and fees

A beachside resort with a wooden deck, palm trees, and a sunset view.

4. Grand Marina Suite - Poolside & Waterfront Condo

Stock Island

CAROL K.

$549 nightly

Nov 10 - Nov 11

Total with taxes and fees

A swimming pool area with multiple pools, palm trees, lounge chairs, and a clear blue sky.

5. Atlantic Parrot | Oceanfront Condo w/ Pool

Beachside

Bill W.

$634 nightly

Nov 18 - Nov 19

Total with taxes and fees

A wooden bridge leading to a house with a sign indicating no swimming or diving.

6. The Tortuga at Sunrise Suites - Balcony & Pool

Key West

Margaret G.

$440 nightly

Dec 1 - Dec 2

Total with taxes and fees

A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

7. The Cat Island Suite | Charmingly Renovated w/ Pool

Key West

Patti E.

$425 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern kitchen with a black countertop, stainless steel sink, and white cabinetry.

8. Waterfront Condo Dock Pool Downtown Near Duval

Meadows

John L.

$354 nightly

Dec 3 - Dec 4

Total with taxes and fees

A tropical garden pathway leading to a building with a yellow facade and green shutters.

9. COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Community Pool!

Old Town Key West

Tracy S.

$394 nightly

Dec 1 - Dec 2

Total with taxes and fees

10. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Old Town Key West

Justin D.

$324 nightly

Dec 1 - Dec 2

Total with taxes and fees

A bedroom with a bed, a nightstand, a lamp, a TV, and a window with curtains.

11. QUIET POUR ~ On Duval St, Adult Only, Adjoining Rum Bar and Near Beach!

Old Town Key West

Stephen N.

$304 nightly

Dec 1 - Dec 2

Total with taxes and fees

A waterfront property with a pool, a thatched-roof structure, and multiple buildings with balconies overlooking the water.

12. Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

Old Town Key West

Amanda M.

$284 nightly

Nov 23 - Nov 24

Total with taxes and fees

A marina with boats docked, a clear sky, and a rainbow.

13. Waterfront Condo Dock Pool Near Duval St

Meadows

Patsy K.

$452 nightly

Nov 16 - Nov 17

Total with taxes and fees

A narrow stone pathway flanked by a yellow building with a white fence and a wall-mounted electrical box.

14. Hidden Key West Cottage - Walk to Duval !!!

Old Town Key West

Regina E.

$254 nightly

Nov 17 - Nov 18

Total with taxes and fees

A wide sandy beach with palm trees and a clear sky.

15. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West

Michelaine a.

$440 nightly

Nov 10 - Nov 11

Total with taxes and fees

A coastal hotel with multiple-story buildings, palm trees, and a well-maintained garden.

16. Gated Parking, Heated Pool - Villa Positano

Old Town Key West

Andrea N.

$640 nightly

Nov 17 - Nov 18

Total with taxes and fees

A modern kitchen with a marble countertop, a built-in oven, and a dining area with a sofa and table.

17. Key West 2BR | Pool, Hot Tub, Balcony & Parking

KEY WEST

Joe B.

$505 nightly

Nov 10 - Nov 11

Total with taxes and fees

18. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Key West

Thadd W.

$440 nightly

Nov 10 - Nov 11

Total with taxes and fees

A modern living room with a sofa, coffee table, and a painting of a beach scene.

19. The Saint Kitts Suite | Breathtaking View, Heated Pool

Key West

Rolando

$428 nightly

Nov 19 - Nov 20

Total with taxes and fees

A beach with people sunbathing and swimming, a clear blue sky, and a calm sea.

20. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

Old Town Key West

Michael R.

$493 nightly

Nov 29 - Nov 30

Total with taxes and fees

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Learn more about Summerland Key

Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favorite seafood shacks serving fresh-caught Keys lobster.

See all hotels in Summerland Key

A coastal pier extending into the sea, surrounded by rocky shores and greenery.

Top reviews in Summerland Key

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

Parmer's Resort

Summerland Key

10/10 Excellent

Michael

A waterfront building with a flat roof, large windows, and a balcony.

Sugar Loaf Lodge

Summerland Key

10/10 Excellent

Upon our arrival, the sight of 2 iguanas on the lounging on the bridge by the pristine water at the back of the property had my entire family out of the minivan at lightning speed. They followed one, which lead them to trees full of these beautiful lizards. The front desk personnel, a very amiable gentleman, was very friendly and welcoming. Our room was in the middle of the 2nd floor, and had a fantastic view of the bay. And yes, there were more iguanas looking at us from the first floor, some...

Momi

A wooden deck with a hanging hammock and a view of a green landscape.

Starlight Serenity - Hideaway w Stunning Views

Summerland Key

10/10 Excellent

max

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

Almond Tree Inn Hotel - Adults Only

Old Town Key West

10/10 Excellent

william

A tropical outdoor area with palm trees, hanging plants, and string lights.

Douglas House - Adults Only

Old Town Key West

10/10 Excellent

Anthony

An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

H2O Suites - Adults Only

Old Town Key West

10/10 Excellent

My husband and I recently stayed at H2O Suites for 3 nights. The property was immaculate, the staff was extremely friendly and helpful, and our room was large and comfortable. We had a suite that had a plunge pool - this was amazing!! We used it several times daily. The location is perfect - one block from Duval, so everything is easily accessed, but it’s very quiet. We rented bikes from the hotel (easy parking right out back) and truly enjoyed our getaway. Cannot day enough good things about...

Erin

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

Alexander's Guesthouse - Adult Exclusive

Old Town Key West

10/10 Excellent

Absolutely wonderful destination fir a relaxing stay while in Key West. Can not say enough about the great staff— friendly, helpful, just happy to be working here. They could not be more accommodating!! Add to that complimentary wine in your room, daily happy hours by the pool, and full service cooked breakfasts that easily saves you hundreds of dollars on a 4- day stay. Can not give this place enough praise. We are already planning a return trip.

Dominick

A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.

The Gardens Hotel

Old Town Key West

10/10 Excellent

Anonymous traveler

A pool area with lounge chairs and a table, surrounded by palm trees.

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Absolutely loved our 5 night stay this past week at Orchid Key!! What a fabulous adult only boutique hotel located just steps off of Duval! We stayed in a Deluxe King the first night because we added on a night at the front end of our trip and it was just off of the pool area and very cozy. Loved the large shower and the room was so clean! Lots of fluffy towels and little extras like free waters and cookies and peppermints were left in the room. The rest of our stay was in a Deluxe King...

Courtney

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

Artist House Key West

Key West Historic District

10/10 Excellent

Anonymous traveler

A modern interior with a staircase, a sofa set, a wooden table, and a television.

Simonton Court Historic Inn & Cottages

Key West Historic District

10/10 Excellent

RADANA

A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

Key West Villas

Old Town Key West

10/10 Excellent

Thys

A porch with a white railing, a bench, and a flag.

The Conch House Heritage Inn

Old Town Key West

10/10 Excellent

Nicholas

A two-story house with a covered porch, a brick pathway, and a large tree.

The Marquesa Hotel

Old Town Key West

10/10 Excellent

David

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

Island City House Hotel

Key West Historic District

10/10 Excellent

Keith

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

The Grand Guesthouse

Old Town Key West

10/10 Excellent

The Grand Guesthouse is a gem in Key West! The host was outstanding and the facility was lovely. Breakfast was simple but nice, and the Happy Hour was an added bonus. We had a nice suite- a bedroom and a living/kitchen area. The room was nicely appointed and it was straightened by the staff each day. The room was very clean! Overall, my wife and I were impressed! Two small improvements... the mattress was too firm. Also, the wifi was not strong enough in our room to stream anything. ...

Anonymous traveler

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

Duval House

Old Town Key West

10/10 Excellent

The Duval House was absolutely precious. The garden courtyard was beautifully taken care of with plenty of nooks to sit in. The pool is mostly shaded for the hottest part of the day, which seemed especially valuable in comparison to other BnBs. Our room was very comfortable with probably the best bed I’ve been in at a hotel or BnB. And all of the staff was very responsive, friendly, and helpful. Even KissKiss, the property cat, made the rounds to our room to make sure everything was in perfect...

Sarah

Frequently Asked Questions

Why book your condo in Summerland Key with Expedia?

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How can I find cheap condos in Summerland Key?

Expedia can help you easily locate cheap condos in Summerland Key. To reserve a superb stay in a couple of clicks, simply use the filter tool to refine your search by budget, amenities and star rating.

What is there to do in Summerland Key near my condo?

The ultimate travel accessory is a well-planned itinerary. Florida Keys Beaches is a wonderful place to begin your sightseeing in Summerland Key.

Search and Rent Summerland Key Condos

Bundle & Save

OneKeyCash

Upfront pricing

Find vacation rentals that suit your style

Check prices for these dates

Our top choices for Summerland Key condo rentals

1. The Curaçao | Key West Condo with Pool, Balcony, & Sunset Views

2. The Grand Cayman | Beautifully Remodeled Key West!

3. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

4. Grand Marina Suite - Poolside & Waterfront Condo

5. Atlantic Parrot | Oceanfront Condo w/ Pool

6. The Tortuga at Sunrise Suites - Balcony & Pool

7. The Cat Island Suite | Charmingly Renovated w/ Pool

8. Waterfront Condo Dock Pool Downtown Near Duval

9. COCONUT PALM SUITE ~ Adult Only, 1 BR, 1 Ba w/ Kitchen and Community Pool!

10. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

11. QUIET POUR ~ On Duval St, Adult Only, Adjoining Rum Bar and Near Beach!

12. Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool

13. Waterfront Condo Dock Pool Near Duval St

14. Hidden Key West Cottage - Walk to Duval !!!

15. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

16. Gated Parking, Heated Pool - Villa Positano

17. Key West 2BR | Pool, Hot Tub, Balcony & Parking

18. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

19. The Saint Kitts Suite | Breathtaking View, Heated Pool

20. OLD TOWN STEPS TO DUVAL! LA DOLCE VITA SLEEPS 2-4, 3 BLOCKS TO SOUTHERNMOST

Learn more about Summerland Key

Top reviews in Summerland Key

Parmer's Resort

10/10 Excellent

Frequently Asked Questions

Why book your condo in Summerland Key with Expedia?

How can I find cheap condos in Summerland Key?

What is there to do in Summerland Key near my condo?

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