Summerland Key Vacation Rentals from AED 2,029: Search Short-Term Rentals

Q: What's the top vacation rental in Summerland Key?

Sugarloaf Key RV Resort & Cottages : This Summerland Key vacation home rental is located near a metro station and offers an outdoor pool, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Summerland Key is Cudjoe Cottages, swimming pool, just 20 miles from Key West .

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Our top choices for Summerland Key vacation rentals

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

Cudjoe Key

James B.

AED 1,972 total

includes taxes & fees

8 Sep - 9 Sep

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

Cudjoe Key

David T.

AED 1,601 total

includes taxes & fees

20 Aug - 21 Aug

Coffee/tea maker, fridge, microwave, oven

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

Summerland Key

John B.

AED 2,029 total

includes taxes & fees

31 Aug - 1 Sep

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

Cudjoe Key

AED 2,354 total

includes taxes & fees

21 Aug - 22 Aug

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

Cudjoe Key

Kiara

AED 2,204 total

includes taxes & fees

24 Aug - 25 Aug

6. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Cudjoe Key

BRIAN S.

AED 1,591 total

includes taxes & fees

21 Aug - 22 Aug

7. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Cudjoe Key

AED 1,886 total

includes taxes & fees

4 Sep - 5 Sep

8. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key

Cheryl V.

AED 2,086 total

includes taxes & fees

15 Aug - 16 Aug

9. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Cudjoe Key

Alisa M.

AED 2,282 total

includes taxes & fees

16 Aug - 17 Aug

10. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Cudjoe Key

Phani U.

AED 2,282 total

includes taxes & fees

17 Aug - 18 Aug

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

Cudjoe Key

"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...

Pauline Y.

AED 2,112 total

includes taxes & fees

15 Aug - 16 Aug

12. Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

Cudjoe Key

Mary T.

AED 2,267 total

includes taxes & fees

9 Sep - 10 Sep

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

Cudjoe Key

Tammy G.

AED 2,235 total

includes taxes & fees

17 Aug - 18 Aug

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

Cudjoe Key

Angela C.

AED 1,897 total

includes taxes & fees

21 Aug - 22 Aug

15. Seabreeze Escape WF RV Lot 489

Cudjoe Key

AED 968 total

includes taxes & fees

8 Sep - 9 Sep

16. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key

jim b.

AED 2,112 total

includes taxes & fees

1 Sep - 2 Sep

17. Starlight Serenity - Hideaway w Stunning Views

Summerland Key

max

AED 2,322 total

includes taxes & fees

17 Aug - 18 Aug

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

Cudjoe Key

Catherine C.

AED 2,333 total

includes taxes & fees

6 Sep - 7 Sep

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

Cudjoe Key

Jennifer S.

AED 2,282 total

includes taxes & fees

14 Aug - 15 Aug

20. Endless Ocean Views - RV589

Cudjoe Key

AED 1,224 total

includes taxes & fees

16 Aug - 17 Aug

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Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

10/10 Excellent

"This facility was clean and beautiful. The "bungalow" was spacious, immaculate, and beautifully maintained. Although we only took advantage of the use of the bungalow, it was superior to staying at a big, name-brand hotel. What a gem!"

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent

"We really enjoyed the privacy and safety of the community. We arrived a little early and were able to gain early access. That was not expected. Then we met Julie, who hand delivered us a delicious key-lime pie! Julie was great throughout our whole stay and accommodated all our needs well beyond our expectations. The place was clean, and the kitchen was loaded with everything you would need to prepare dinner/drinks at home. The bikes were a treat. We used them to roam around or when the kids wanted to fish/swim. The balcony is beautiful with a nice sunrise view. The only suggestion i would make is if your'e bringing more then one vehicle, figure out the overflow parking before hand. There is a one vehicle limit that got a bit confusing in the later hours."

Cottage with swimming pool and dockage, just minutes to Key West!

10/10 Excellent

"This location was perfect for what my husband and I needed. We brought our boat and were able to use the dock throughout our stay. We did have an issue with the AC system and Jennifer was great by putting us into another one of their units overnight until our units AC was fixed the next day. This will definitely be a spot we use again in the future."

Charming cottages, dockage, pool, just minutes to Key West

8/10 Good

"The whole time was great, location was awesome. The queen bed was broken though. If that wasn’t the case I would have nothing but great things to say. I would consider visiting again. It was a nice place overall. Thank you."

Cottage with Pool and Dockage, just minutes to Key West

8/10 Good

"We thought the grounds and location were perfect centrally located to everything you could want to do in the lower Keys. Host and check in process was extremely smooth and clear from start to finish. The actual cottage/unit needs a thorough cleaning, dishes were dirty and the towels/linens didn’t seem like they were recently changed and unfortunately the beds were very uncomfortable. If this unit was a little cleaner and had comfortable beds I’d book this cottage every time I visited the Keys. I absolutely love the grounds and peaceful location."

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

10/10 Excellent

"This property was perfect for our stay. My nine year old son caught and released over 50 fish right off the back. The water was beautiful and the things for families to do at Venture Out are great!"

Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Summerland Key?

Sugarloaf Key RV Resort & Cottages: This Summerland Key vacation home rental is located near a metro station and offers an outdoor pool, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Another good choice for your trip to Summerland Key is Cudjoe Cottages, swimming pool, just 20 miles from Key West.

How many vacation rentals are there in Summerland Key?

Choose from 473 Expedia vacation rentals in Summerland Key for a memorable vacation.

What can I see and do in Summerland Key?

Florida Keys Beaches and Upper Sugarloaf Key are a couple of lovely local spots to get outside and enjoy nature. Venture Key and Venture Out Keys are other places to visit while you're in town.

What are vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.

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Check prices for these dates

Our top choices for Summerland Key vacation rentals

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

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

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

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

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

6. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

7. Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

8. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

9. Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

10. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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

12. Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

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

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

15. Seabreeze Escape WF RV Lot 489

16. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

17. Starlight Serenity - Hideaway w Stunning Views

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

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

20. Endless Ocean Views - RV589

Find vacation rentals that suit your style

Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Sugarloaf Key Hotel at KOA Resort

Springs Venture Out Dolphin House #386 with beautiful open water views

Cottage with swimming pool and dockage, just minutes to Key West!

Charming cottages, dockage, pool, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

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