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

Holiday Homes in Summerland Key

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Summerland Key holiday homes

Exterior

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

SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (110 reviews)
"Stay was great. We met the hosts and they were wonderful people."
United States
James B.
The price is €369
includes taxes & fees
2 Sept - 3 Sept
SAVE BIG $$$ AUG/SEPT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Private kitchen

2. Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
United States
John B.
The price is €440
includes taxes & fees
2 Sept - 3 Sept
Kelly's Kabin - Adorable Private Summerland Key Cottage
Exterior detail

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
United States
Kiara
The price is €504
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Exterior

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

SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (95 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is €430
includes taxes & fees
1 Sept - 2 Sept
SAVE BIG $$$ AUG/SEPT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Beach

5. 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
9.6 out of 10, Exceptional, (4 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is €529
includes taxes & fees
30 Aug - 31 Aug
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Pool

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
8.0 out of 10, Very good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
United States
jim b.
The price is €495
includes taxes & fees
1 Sept - 2 Sept
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Beach

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
9.4 out of 10, Exceptional, (17 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is €524
includes taxes & fees
2 Sept - 3 Sept
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
House

8. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
United States
max
The price is €520
includes taxes & fees
30 Aug - 31 Aug
Starlight Serenity - Hideaway w Stunning Views
Pool

9. 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
8.8 out of 10, Excellent, (11 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is €529
includes taxes & fees
30 Aug - 31 Aug
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Beach

10. Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
9.0 out of 10, Wonderful, (2 reviews)
"This was a sweet little modular home that gave us a clean and comfortable place to stay… away from the tourist scene."
United States
Nora Kay F.
The price is €506
includes taxes & fees
1 Sept - 2 Sept
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Terrace/patio

11. Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly

Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly
Cudjoe Key
The price is €548
includes taxes & fees
1 Sept - 2 Sept
Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly
Terrace/patio

12. Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is €485
includes taxes & fees
30 Aug - 31 Aug
Starlight Serenity - Hideaway with Stunning Views
Beach

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

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
9.0 out of 10, Wonderful, (11 reviews)
"This property is convenient to food and fun. It was very clean, comfortable and we felt safe to walk around the resort. We had a wonderful stay here."
United States
Catherine C.
The price is €550
includes taxes & fees
6 Sept - 7 Sept
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Pool

14. 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
10.0 out of 10, Exceptional, (4 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is €558
includes taxes & fees
6 Sept - 7 Sept
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Beach

15. Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.4 out of 10, Exceptional, (6 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is €521
includes taxes & fees
24 Sept - 25 Sept
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Beach

16. Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views

Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Cudjoe Key
9.4 out of 10, Exceptional, (14 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is €558
includes taxes & fees
10 Sept - 11 Sept
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
Beach

17. Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is €552
includes taxes & fees
30 Aug - 31 Aug
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Pool

18. Florida keys Waterfront,Forever Summer

Florida keys Waterfront,Forever Summer
Summerland Key
9.4 out of 10, Exceptional, (6 reviews)
"We had a great time. Everything was what we were told. Michael was a great host."
United States
Sara B.
Florida keys Waterfront,Forever Summer
Pool

19. Sailfish Haven #390 - Ocean Views, 35' seawall

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (8 reviews)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
The price is €531
includes taxes & fees
11 Sept - 12 Sept
Sailfish Haven #390 - Ocean Views, 35' seawall
Beach

20. Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very good, (2 reviews)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is €535
includes taxes & fees
2 Sept - 3 Sept
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
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

8/10 Good
"The staff at Parmer’s is excellent from the check-in person to everyone that works on the grounds. However, this place had to grow on me because my initial reaction was one of disappointment. I think the pictures look much better than what’s actually there. The beach that’s advertised and looks like a sandy oasis with a clean shoreline is actually about sandy to mid calf and then algae and seaweed. A nice place to catch some rays with nice loungers but sitting on the waters edge but not for swimming or wading. The furniture is straight out of the 60’s or 70’s, but is clean and well kept. The A/C is enough to keep the cottage type bungalow cool but too far from the bathroom to keep that area cool. The pool is super clean and well maintained but water too hot during summer and would benefit from the pump keeping water flowing longer. Having said all this I found Parmer’s growing on us because of the staff, the light breakfast, eagerness of staff to please providing a fan to keep the bath cooler, the boat ramp, kayaks, shaded sitting areas by the water, fishing on property and the overall laid back feeling made me forget what wasn’t perfect and remember what hotel stays were like when I was young. No fancy Marriott’s or Sheraton, but just a place where you felt you hadn’t left home, but gained a water view with a summer breeze."
George 3-night trip
Posted 4 hours ago
Parmer's Resort

Find out more about Summerland Key

Summerland Key Holiday Homes information

Number of reviews
308
Accommodation
384 Holiday Homes
Lowest Price
€369
Highest Price
€558