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
31 July - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 Nov

Our top choices for Summerland Key holiday homes

Exterior

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

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (93 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is AU$614
includes taxes & fees
20 July - 21 July
SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool

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
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
United States
Cheryl V.
The price is AU$808
includes taxes & fees
19 July - 20 July
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A heated pool

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, (10 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 AU$872
includes taxes & fees
24 July - 25 July
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Beach

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
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is AU$882
includes taxes & fees
19 July - 20 July
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Coffee/tea maker, fridge, microwave, oven

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (125 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 AU$746
includes taxes & fees
10 Aug - 11 Aug
Kelly's Kabin - Adorable Private Summerland Key Cottage
A heated pool

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 AU$842
includes taxes & fees
24 July - 25 July
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Beach

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 AU$900
includes taxes & fees
19 July - 20 July
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Exterior detail

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is AU$913
includes taxes & fees
17 Aug - 18 Aug
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Beach

Canal-view 2BR/2BA home with pool, hot tub, and dock access.

Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Cudjoe Key
9.2 out of 10, Wonderful, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is AU$881
includes taxes & fees
26 July - 27 July
Canal-view 2BR/2BA home with pool, hot tub, and dock access.
Beach

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
8.0 out of 10, Very good, (1 review)
"The unit was very old and tired. As such, several windows did not open, the cook top light was not working, the shower surround was cracked and the joint caulking was bad to name some examples. However, the place was spotless when we arrived and with (needed) working AC. The kitchen is WELL appointed with cooking items, some spices, and baking supplies. The washer/dryer was a treat as we travel light. The waterfront deck/patio area was great for morning coffee and evening cocktails. Venture out...
United States
Pauline Y.
The price is AU$823
includes taxes & fees
24 July - 25 July
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Beach

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 AU$881
includes taxes & fees
19 July - 20 July
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
Outdoor pool, a heated pool

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Cudjoe Key
7.8 out of 10, Good, (20 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is AU$740
includes taxes & fees
24 July - 25 July
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
A heated pool

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Cudjoe Key
8.0 out of 10, Very good, (1 review)
The price is AU$890
includes taxes & fees
20 July - 21 July
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Property grounds

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is AU$845
includes taxes & fees
19 July - 20 July
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Beach

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, (13 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is AU$939
includes taxes & fees
19 July - 20 July
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
A heated pool

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 AU$964
includes taxes & fees
3 Aug - 4 Aug
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Beach

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 AU$940
includes taxes & fees
19 July - 20 July
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Beach

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
9.2 out of 10, Wonderful, (15 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AU$851
includes taxes & fees
17 Aug - 18 Aug
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A heated pool

Sailfish Haven #390 - Ocean Views, 35' seawall

Sailfish Haven #390 - Ocean Views, 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (7 reviews)
"It was a perfect home to stay in cudokey"
United States
Patricia H.
Sailfish Haven #390 - Ocean Views, 35' seawall
Beach

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

Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Unit was as shown in the pictures, so no unpleasant surprises. Very much appreciated the clean smell of the house. "
United States
Marilyn D.
The price is AU$1,006
includes taxes & fees
14 Aug - 15 Aug
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
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
"We loved this place. I think it was an old fishing camp. Not new but it was perfect for our stay! We would stay again. Comfy bed, hot water, nice view!"
Patricia 5-night trip
Posted 15 hours ago
Parmer's Resort

Find out more about Summerland Key

Summerland Key Holiday Homes information

Number of reviews
344
Accommodation
389 Holiday Homes
Lowest Price
AU$614
Highest Price
AU$1,006