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

Search Condos Rentals in Summerland Key from CA $402

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Summerland Key condo rentals

A beach with lounge chairs, palm trees, and a water body.

1. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (35 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
The price is CA $353
CA $804 total
includes taxes & fees
Oct 26 - Oct 27
Grand Marina Suite - Poolside & Waterfront Condo
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

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

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is CA $245
CA $709 total
includes taxes & fees
Oct 29 - Oct 30
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A modern living room with a sofa, coffee table, and a painting of a beach scene.

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

The Saint Kitts Suite | Breathtaking View, Heated Pool
Key West
9.8 out of 10, Exceptional, (11 reviews)
"Excellent place to stay."
United States
Rolando
The price is CA $245
CA $709 total
includes taxes & fees
Oct 29 - Oct 30
The Saint Kitts Suite | Breathtaking View, Heated Pool
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

4. Pool View Suite | Beachside Resort

Pool View Suite | Beachside Resort
Key West
8.0 out of 10, Very good, (3 reviews)
"It was a holiday weekend. Key West in general all lodging was expensive. The room was very comfortable and clean. More than enough room. I was on the water which was amazing. The pool area was very awesome. Love that they have a bar and restaurant available. All the available excursions. I took advantage of the Sunset Tour. Property manager was available for any questions. Beachside staff was also very helpful. Would definitely visit again. Great Experience!! Thank you."
United States
Christie Y.
The price is CA $238
CA $427 total
includes taxes & fees
Oct 21 - Oct 22
Pool View Suite | Beachside Resort
A swimming pool area with multiple pools, palm trees, lounge chairs, and a clear blue sky.

5. Atlantic Parrot | Oceanfront Condo w/ Pool

Atlantic Parrot | Oceanfront Condo w/ Pool
Beachside
9.8 out of 10, Exceptional, (10 reviews)
"Absolutely beautiful property as well as room I loved it everything about it was beautiful "
United States
Misty C.
The price is CA $216
CA $1,061 total
includes taxes & fees
Oct 25 - Oct 26
Atlantic Parrot | Oceanfront Condo w/ Pool
A bedroom with a bed, a nightstand, a lamp, a TV, and a window with curtains.

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

QUIET POUR ~ On Duval St, Adult Only, Adjoining Rum Bar and Near Beach!
Old Town Key West
9.8 out of 10, Exceptional, (6 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great property, location! Exceptionally clean"
United States
A guest from Kendall Park, NJ
The price is CA $163
CA $402 total
includes taxes & fees
Oct 21 - Oct 22
QUIET POUR ~ On Duval St, Adult Only, Adjoining Rum Bar and Near Beach!
A bedroom with a bed, a chair, a wardrobe, and a bathroom visible through an open door.

7. The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!

The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
Key West
10.0 out of 10, Exceptional, (2 reviews)
"This condo was perfect for our 2 day stay in the beautiful Key West. About 8 minutes from Duvall on the golf cart! The pool and hot tub was very clean as well!"
United States
Amy Jordan P.
The price is CA $247
CA $711 total
includes taxes & fees
Oct 21 - Oct 22
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
A hotel with a swimming pool, multiple balconies, and lush greenery.

8. 2BR suite | Pool | Hot Tub | Tennis | W/D

2BR suite | Pool | Hot Tub | Tennis | W/D
Key West
The price is CA $216
CA $581 total
includes taxes & fees
Oct 25 - Oct 26
2BR suite | Pool | Hot Tub | Tennis | W/D
Waterfront Condo

9. Waterfront Dock Pool Condo Near Duval St Pet OK

Waterfront Dock Pool Condo Near Duval St Pet OK
Meadows
9.4 out of 10, Exceptional, (48 reviews)
"Hosts are super responsive and helpful. Perfect location. Would absolutely stay here again! "
United States
Amber G.
The price is CA $240
CA $635 total
includes taxes & fees
Oct 25 - Oct 26
Waterfront Dock Pool Condo Near Duval St Pet OK
A bedroom with a bed, a ceiling fan, a nightstand with a lamp, a window with curtains, and a view of the outside.

10. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful condo. Wonderful host. Wonderful location. Great for family of 6. Beautifully decorated and very spacious. Loved the large balcony. Host offered suggestions and responded almost immediately to any questions or needs. Very impressed."
United States
Patsy K.
The price is CA $227
CA $619 total
includes taxes & fees
Oct 25 - Oct 26
Waterfront Condo Dock Pool Near Duval St
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

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

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is CA $245
CA $709 total
includes taxes & fees
Oct 29 - Oct 30
The Cat Island Suite | Charmingly Renovated w/ Pool
A fish cleaning station with a sign, wooden structure, and water.

12. Waterfront Dock Pool Key West Near Duval

Waterfront Dock Pool Key West Near Duval
Meadows
10.0 out of 10, Exceptional, (41 reviews)
"Clean, comfy and had everything we expected."
United States
Chrystalbelle R.
The price is CA $189
CA $572 total
includes taxes & fees
Oct 26 - Oct 27
Waterfront Dock Pool Key West Near Duval
A tropical garden pathway leading to a building with a yellow facade and green shutters.

13. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (139 reviews)
"Great place to stay"
United States
walter l.
The price is CA $209
CA $477 total
includes taxes & fees
Oct 26 - Oct 27
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A pool area with a clear blue pool, surrounded by palm trees and a white fence.

14. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
The price is CA $268
CA $742 total
includes taxes & fees
Oct 21 - Oct 22
The Tortuga at Sunrise Suites - Balcony & Pool
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 Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
The price is CA $501
CA $770 total
includes taxes & fees
Oct 25 - Oct 26
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A waterfront property with a pool, a thatched-roof structure, and multiple buildings with balconies overlooking the water.

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

Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool
Old Town Key West
9.0 out of 10, Wonderful, (25 reviews)
"Super cute place. "
United States
Amanda M.
The price is CA $159
CA $464 total
includes taxes & fees
Nov 3 - Nov 4
Pierre's Perch: Discover Charm and Convenience, Perfect Studio Retreat in Key West with Shared Pool
A bedroom with a wooden four-poster bed, a nightstand, a dresser, a television, and a ceiling fan.

17. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.2 out of 10, Wonderful, (14 reviews)
"Beautiful location and really nice layout "
United States
Janey
The price is CA $353
CA $804 total
includes taxes & fees
Oct 26 - Oct 27
Grand Marina Suite - Poolside & Waterfront Condo
A swimming pool with lounge chairs and palm trees, surrounded by a fence.

18. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.2 out of 10, Wonderful, (26 reviews)
"Great stay"
United States
Dustin H.
The price is CA $353
CA $804 total
includes taxes & fees
Oct 26 - Oct 27
Grand Marina Suite - Poolside & Waterfront Condo
A beach path leading to the ocean with palm trees and a wooden fence.

19. Magical Ocean Penthouse Top-Floor Ocean View Condo. Feel the magic.

Magical Ocean Penthouse Top-Floor Ocean View Condo. Feel the magic.
Beachside
9.8 out of 10, Exceptional, (236 reviews)
"Condo was clean and beautiful. Pool area was gorgeous. Cannot wait to get back!"
United States
carol c.
The price is CA $473
CA $1,130 total
includes taxes & fees
Oct 30 - Oct 31
Magical Ocean Penthouse Top-Floor Ocean View Condo. Feel the magic.
A wide sandy beach with palm trees and a clear sky.

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

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (49 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is CA $501
CA $770 total
includes taxes & fees
Oct 25 - Oct 26
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
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
"Stay was perfect. Staff was kind and outgoing. Bed was comfortable and place was very clean. Only thing I would change is the single serve coffee makers. A drip pot would be so much more convenient. They do have Babies coffee in the dining hall at breakfast and I can not complain about that. I love Babies coffee. I will stay here again."
Denis 3-night trip
Posted 1 day ago
Parmer's Resort

Find out more about Summerland Key

Summerland Key Condo Rentals information

Number of reviews
682
Accommodation
1 Condo Rentals
Lowest Price
CA $402
Highest Price
CA $1,061

Frequently asked questions

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