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

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Summerland Key vacation homes

A waterfront property with a multi-story building featuring balconies, a dock, and a landscaped garden with palm trees.

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

SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.6 out of 10, Exceptional, (98 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is ￥21,941
￥66,415 total
includes taxes & fees
Oct 6 - Oct 7
SAVE BIG $$$ OCT./NOV. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

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, (129 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 ￥31,254
￥80,090 total
includes taxes & fees
Oct 11 - Oct 12
Kelly's Kabin - Adorable Private Summerland Key Cottage
Pool

3. 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 ￥24,861
￥72,109 total
includes taxes & fees
Oct 6 - Oct 7
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A two-story building with a blue exterior, white railings, and a staircase leading to the upper floor.

4. 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 ￥28,981
￥91,226 total
includes taxes & fees
Oct 7 - Oct 8
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is ￥25,098
￥69,967 total
includes taxes & fees
Oct 13 - Oct 14
SAVE BIG $$$ OCT./NOV. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

6. 2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.

2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Cudjoe Key
The price is ￥35,635
￥85,176 total
includes taxes & fees
Oct 9 - Oct 10
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Pool

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
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 ￥27,348
￥75,221 total
includes taxes & fees
Oct 6 - Oct 7
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

8. 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, (18 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is ￥31,491
￥80,514 total
includes taxes & fees
Oct 6 - Oct 7
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
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 ￥33,149
￥82,537 total
includes taxes & fees
Oct 6 - Oct 7
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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 ￥29,005
￥77,402 total
includes taxes & fees
Oct 6 - Oct 7
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

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

Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Cudjoe Key
9.6 out of 10, Exceptional, (7 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is ￥31,491
￥80,514 total
includes taxes & fees
Oct 6 - Oct 7
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
A wooden deck with a railing, wicker chairs, and a view of greenery.

12. 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 ￥42,429
￥105,356 total
includes taxes & fees
Oct 14 - Oct 15
Starlight Serenity - Hideaway w Stunning Views
A wooden deck with a hanging hammock and a view of a green landscape.

13. 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 ￥33,938
￥96,961 total
includes taxes & fees
Oct 14 - Oct 15
Starlight Serenity - Hideaway with Stunning Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

14. 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 ￥33,149
￥82,537 total
includes taxes & fees
Oct 6 - Oct 7
Waterfront 2BR/2BA with 35' Dock – Island Breeze Keys Escape
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

15. 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, (5 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is ￥33,149
￥83,011 total
includes taxes & fees
Oct 6 - Oct 7
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
An aerial view of a resort with a large pool, palm trees, and a pier.

16. Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Really nice unit, well equipped, and quiet.Would stay again for sure."
United States
Tom A.
The price is ￥55,248
￥106,786 total
includes taxes & fees
Oct 12 - Oct 13
Spanish Queen @Venture Out, Cudjoe Key
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

17. 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, (12 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 ￥34,806
￥84,718 total
includes taxes & fees
Oct 7 - Oct 8
Salty Breeze #161 Canal-Front Retreat with Dock, Pool & Ocean Views
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

18. 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
8.0 out of 10, Very good, (21 reviews)
"Heated pool was very nice, and location of rental."
United States
Angela C.
The price is ￥39,068
￥81,047 total
includes taxes & fees
Oct 7 - Oct 8
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Pool

19. 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 ￥37,292
￥87,829 total
includes taxes & fees
Oct 6 - Oct 7
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

20. 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, (16 reviews)
"Great water view and comfortable for four adults "
United States
Kyle F.
The price is ￥35,635
￥85,650 total
includes taxes & fees
Oct 6 - Oct 7
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys 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

Looe Key Reef Resort

Looe Key Reef Resort

10/10 Excellent
"The room was super clean. The fact that we can keep a boat docked right behind our room is amazing. There is a tiki bar literally right in front of the room is a plus. Check out was easy and quick as well as check in. I mean best decision ever."
anneliss 2-night trip
Posted 2 days ago
Looe Key Reef Resort

Find out more about Summerland Key

Summerland Key Vacation Homes information

Number of reviews
347
Accommodation
377 Vacation Homes
Lowest Price
￥66,415
Highest Price
￥106,786