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

Summerland Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (97 reviews)
"Great location, wonderful hosts!"
United States
Blue Mountain Footwear F.
The price is CA $183
CA $581 total
includes taxes & fees
Sep 30 - Oct 1
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A waterfront property with a covered porch, a boat dock, and a clear sky.

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

SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (112 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
United States
Mckayla S.
The price is CA $183
CA $581 total
includes taxes & fees
Sep 30 - Oct 1
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A modern kitchen with granite countertops, stainless steel appliances, and light-colored cabinetry.

3. 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 CA $281
CA $722 total
includes taxes & fees
Oct 3 - Oct 4
Kelly's Kabin - Adorable Private Summerland Key Cottage
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 CA $255
CA $815 total
includes taxes & fees
Sep 30 - Oct 1
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
A swimming pool with a tiled edge, surrounded by lounge chairs and umbrellas, under a cloudy sky.

5. 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 CA $350
CA $728 total
includes taxes & fees
Oct 2 - Oct 3
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Pool

6. 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 CA $223
CA $647 total
includes taxes & fees
Oct 2 - Oct 3
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
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 CA $245
CA $675 total
includes taxes & fees
Oct 2 - Oct 3
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
A marina with multiple docked boats, a variety of residential buildings, and a clear view of the surrounding water.

8. Florida Keys Waterfront Escape - 2BR with 44' Seawall

Florida Keys Waterfront Escape - 2BR with 44' Seawall
Cudjoe Key
The price is CA $334
CA $788 total
includes taxes & fees
Oct 2 - Oct 3
Florida Keys Waterfront Escape - 2BR with 44' Seawall
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

9. 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 CA $297
CA $741 total
includes taxes & fees
Oct 2 - Oct 3
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Pool

10. 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 CA $297
CA $744 total
includes taxes & fees
Oct 5 - Oct 6
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.

11. 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 CA $282
CA $723 total
includes taxes & fees
Sep 30 - Oct 1
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

12. 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 CA $260
CA $695 total
includes taxes & fees
Sep 30 - Oct 1
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.

13. 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 CA $319
CA $770 total
includes taxes & fees
Sep 30 - Oct 1
Sea La Vie #197 Oceanfront Home with 49' Dock, Heated Pool & Florida Keys Views
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

14. 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 CA $282
CA $723 total
includes taxes & fees
Sep 30 - Oct 1
Mahi House #440 Waterfront Retreat with Dock, Pool & Optional Golf Cart
Pool

15. 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 CA $319
CA $770 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Pool

16. 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 CA $304
CA $751 total
includes taxes & fees
Sep 30 - Oct 1
Sailfish Haven #390 - Ocean Views, 35' seawall
A wooden deck with a hanging hammock and a view of a green landscape.

17. 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 CA $247
CA $804 total
includes taxes & fees
Sep 30 - Oct 1
Starlight Serenity - Hideaway with Stunning Views
A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a glass table and blue patterned chairs.

18. 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 CA $334
CA $776 total
includes taxes & fees
Oct 5 - Oct 6
Waterfront 2BR/2BA with 35' Dock, Kayaks, Bikes & Pet-Friendly
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.

19. 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 CA $319
CA $770 total
includes taxes & fees
Oct 2 - Oct 3
2BR, 2BA Cudjoe Key Home with pool, hot tub, and patio.
Pool

20. 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 CA $282
CA $723 total
includes taxes & fees
Sep 30 - Oct 1
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
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

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"I have nothing but nice things to say about the hotel, staff and property. You are welcomed with a happy and professional staff, and given first class service. The suites are pristine, well appointed and beautifully decorated with comfortable furnishings. You even get a washer and dryer in your unit. Parking is right under the units and there is a large elevator with luggage carts as well. The views are beautiful with a fantastic boat ramp for those with boats. Long story short, it is a must stay!"
Susan 4-night trip
Posted 15 hours ago
Sugarloaf Key Hotel at KOA Resort

Find out more about Summerland Key

Summerland Key Vacation Homes information

Number of reviews
311
Accommodation
383 Vacation Homes
Lowest Price
CA $581
Highest Price
CA $815

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