Search Vacation Homes in Summerland Key

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Check prices for these dates

Next weekend
16 May - 18 May
In two weeks
23 May - 25 May
In one month
6 Jun - 8 Jun
In two months
4 Jul - 6 Jul

Compare 357 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (146)
"Good location "
The price is AED 1,102
AED 2,327 total
includes taxes & fees
20 May - 21 May
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Outdoor dining

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

8.8 out of 10, Excellent, (139)
"Great location and house was clean. "
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Private Secluded Ocean View & Pool Near Key West
Outdoor pool, a heated pool

Private Secluded Ocean View & Pool Near Key West

8.4 out of 10, Very Good, (90)
"Property was as advertised "
Private Secluded Ocean View & Pool Near Key West
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Shower, hair dryer, towels

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

10.0 out of 10, Exceptional, (1)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock. "
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Outdoor dining

COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

9.6 out of 10, Exceptional, (34)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (73)
"Clean well equipped great location"
Old Florida Style, wrap around porch, boat basin for dockage, open water
One of the very few beach houses with a daily, rental license in the Keys.
Outdoor pool

One of the very few beach houses with a daily, rental license in the Keys.

8.8 out of 10, Excellent, (59)
"The house is special, it transmits a lot of peace next to that spectacular dock where the fishing is fabulous, everything is very clean and well equipped with cauldrons etc.I will be back 100%"
The price is AED 1,980
AED 4,833 total
includes taxes & fees
21 May - 22 May
One of the very few beach houses with a daily, rental license in the Keys.
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Balcony

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

8.4 out of 10, Very Good, (109)
"The whole experience was decent until the last night. We met with a lot of termites and two cockroaches"
The price is AED 826
AED 1,980 total
includes taxes & fees
12 May - 13 May
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
A heated pool

Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill

9.8 out of 10, Exceptional, (218)
"Good accomodations"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Beach nearby

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

8.6 out of 10, Excellent, (81)
"We were very happy with this VRBO and would stay again. Some attention to cleaning out drawers and dusting behind things should be addressed. Everything else was so nice we still give it 5 stars. "
The price is AED 1,194
AED 2,659 total
includes taxes & fees
3 Jun - 4 Jun
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Relax by Florida Keys Beaches, just a 7-min drive away
Beach

Relax by Florida Keys Beaches, just a 7-min drive away

9.8 out of 10, Exceptional, (191)
"Small house in a nice gated community. Check in was easy. Stayed during a family vacation with 4 adults and a 10 year old. "
Relax by Florida Keys Beaches, just a 7-min drive away
Mahi House #440 - 35' seawall
A heated pool

Mahi House #440 - 35' seawall

The price is AED 1,185
AED 2,550 total
includes taxes & fees
12 May - 13 May
Mahi House #440 - 35' seawall
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Miscellaneous

Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear

9.8 out of 10, Exceptional, (118)
"Clean and comfortable"
Walk to Beach, Open Water View from porch , dock, bikes, kayaks & snorkel gear
Reel Island Retreat #273 at Venture Out in the Florida Keys
A heated pool

Reel Island Retreat #273 at Venture Out in the Florida Keys

9.6 out of 10, Exceptional, (4)
"The staff at Venture one was absolutely amazing. The home we stayed in was also a great location. Dated but clean. Definitely will stay at Venture again !"
The price is AED 1,031
AED 2,329 total
includes taxes & fees
10 May - 11 May
Reel Island Retreat #273 at Venture Out in the Florida Keys
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Outdoor dining

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

9.6 out of 10, Exceptional, (90)
"The residence was as shown on VRBO. The bedrooms were “tight” but it worked just fine for 2 couples. Convenient to the Keys "
The price is AED 731
AED 1,834 total
includes taxes & fees
20 May - 21 May
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
TV

Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!

9.6 out of 10, Exceptional, (65)
"Great location if you are good with being away from the madness of key west. Pool is great and love the food nearby. "
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Marina

Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5

10.0 out of 10, Exceptional, (222)
"Great location and a clean home. "
Beautiful Family-Friendly, Dock, Marina, Heated Pool, near Key West, MM21.5
Sunny Gens - Venture Out #606
Smart TV, table tennis

Sunny Gens - Venture Out #606

6.0 out of 10, (1)
Sunny Gens - Venture Out #606
**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY
Terrace/patio

**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY

9.4 out of 10, Exceptional, (13)
"House was clean and quaint. Good location; close enough to Key West but away from the hustle and bustle. Good restaurants only a short drive away. "
**KEYSIE DOES IT @ CUDJOE KEY** Private Home in Waterfront Community + LAST KEY
Sailfish Haven #390 - Ocean Views, 35' seawall
A heated pool

Sailfish Haven #390 - Ocean Views, 35' seawall

8.0 out of 10, Very Good, (4)
"We really enjoyed our stay. The home was exactly as advertised which we definitely appreciated. It was nice to have the kitchen with a wine opener and decent dishes. Being on the water was a plus for our cousin specifically but enjoyed by all. We sat on the back deck morning and night. It was fun to watch the pelicans and boats. Definitely highly recommend. "
The price is AED 973
AED 2,282 total
includes taxes & fees
17 May - 18 May
Sailfish Haven #390 - Ocean Views, 35' seawall
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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Other property types in Summerland Key

Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (136)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (175)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
Direct Oceanfront Cottage-Sunrise View- #2,
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (146)
"Good location "
The price is AED 1,102
AED 2,327 total
includes taxes & fees
20 May - 21 May
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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.