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Check prices for these dates

Next weekend
21 Mar - 23 Mar
In two weeks
28 Mar - 30 Mar
In one month
11 Apr - 13 Apr
In two months
9 May - 11 May

Compare 295 Vacation Homes in Summerland Key with updated reviews, rates, and availability.

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, (133)
"My sister and friend from north Alabama and my youngest daughter and I decided on a last minute mini vacation. We found this little gem of a place while looking for places to stay in the Keys. Although it could use some TLC, we found the property to be clean, well-stocked and perfect for a short stay, some family time, rest and relaxation. We truly enjoyed our stay and would definitely consider staying here again,"
The price is AED 1,083
AED 2,306 total
includes taxes & fees
13 Mar - 14 Mar
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, (86)
"Nice property. We enjoyed our stay."
Private Secluded Ocean View & Pool Near Key West
Waterfront Captain House with Boat Basin & Ramp!
Outdoor dining

Waterfront Captain House with Boat Basin & Ramp!

9.8 out of 10, Exceptional, (7)
"Beautiful property comfortable beds! We enjoyed fishing in the lagoon. This is a beautiful home!"
Waterfront Captain House with Boat Basin & Ramp!
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, (103)
"Definitely need to update the property. Day to day cleanliness was good but many burnt out light bulbs or mismatched bulbs. A coat of paint and updated furniture would help. House A has no view of the water and may have chosen a different place in the complex if i had known. Pool was well taken care of and lots of privacy by the home. Convenient to Key west and lots of good local restaurant choices. Beds were very comfortable. "
The price is AED 1,083
AED 2,306 total
includes taxes & fees
22 Mar - 23 Mar
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
Exterior

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

9.8 out of 10, Exceptional, (236)
"Property was in a wonderful gated community with ocean views very convenient to Key West & other lower keys. The property was very clean & well stocked with everything for the kitchen. It was comfortable, befs were great & visit was very enjoyable."
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security
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, (190)
"30 minutes to Key West; great local restaurants (highly recommend the Square Grouper) and within minutes of biking/walking trails. A wonderful location and a well appointed house. We loved it!"
Relax by Florida Keys Beaches, just a 7-min drive away
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 2,200
AED 4,877 total
includes taxes & fees
16 Mar - 17 Mar
One of the very few beach houses with a daily, rental license in the Keys.
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, (138)
"This house is on stilts, and the views from the Atlantic-facing side are amazing! You look over the treetops and see the ocean from the kitchen, dining area, one bedroom, and the giant screened-in porch! The view is expansive enough to give you a glimpse of both sunrise and sunset. When we were at the house, we spent much of our time on the porch -- we really didn't want to leave. The pool right behind the house was enjoyable and seemed very clean. The location is great -- only 30 minutes...
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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, (210)
"What a perfect location. Impeccable home with adorable decor. It was perfectly equipped with everything and more than we even thought of.I would give 10 stars and I'm a neat freak!!!"
Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
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

9.0 out of 10, Wonderful, (2)
"The property was extremely clean. It was a nice location easy to get to everything we wanted to do. The only thing we found lacking was a king bed was in the listing turned out. It was a trundle bed with king sheets. That was very disappointing as it is not comfortable for two adult adults to sleep on a trundle bed together Ended up using the second bedroom to sleep."
The price is AED 973
AED 2,245 total
includes taxes & fees
11 Apr - 12 Apr
Reel Island Retreat #273 at Venture Out in the Florida Keys
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, (64)
"Very nice and clean. Comfortable . Really enjoyed our stay "
Direct Ocean View! 5 Bed/3 Bath with room for everyone. Large pool and Dock!
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, (68)
"The house is portrayed accurately in the listing. We loved the location (close enough to restaurants and Key West and Bahia Honda, but away from the crowds)The private cove/boat docking area was great. The family fished very successfully from the sea wall and from inside the cove. We rented a kayak and launched easily from the yard. We chartered a boat and the captain picked us up in the cove - so convenient. We enjoyed sunrise and coffee on the porch every morning."
The price is AED 1,653
AED 3,260 total
includes taxes & fees
20 Mar - 21 Mar
Old Florida Style, wrap around porch, boat basin for dockage, open water
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
On the beach, sun loungers, beach towels

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes

9.8 out of 10, Exceptional, (223)
"Great week in the Florida Keys. Home was extremely clean, very well equipped, had everything you needed to make you feel at home. Each bedroom had it's own ensuite bath and it was perfect for two couples. Location was excellent and would not hesitate to book here again.Thanks Melanie!"
The price is AED 1,469
AED 3,211 total
includes taxes & fees
22 Mar - 23 Mar
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
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

8.8 out of 10, Excellent, (76)
"Property was very clean. Kitchen is well stocked with equipment. Location and pool were excellent. Pool furniture needed repair. Master bath needs some repair on shower door and vanity. First guest room bed needs replacement. Difficult to find the driveway entrance from the highway. "
The price is AED 1,102
AED 2,563 total
includes taxes & fees
20 Mar - 21 Mar
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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, (86)
"We really loved the home and the community where the home was located. Nice and quiet. It suited our needs perfectly. Home was very clean "
The price is AED 1,282
AED 2,527 total
includes taxes & fees
31 Mar - 1 Apr
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
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!

9.4 out of 10, Exceptional, (29)
"Excellent views, very quiet, pool was outstanding "
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Waterfront Anchor House with Boat Basin & Ramp!
Sun loungers, beach towels

Waterfront Anchor House with Boat Basin & Ramp!

9.6 out of 10, Exceptional, (15)
"Very pleasant host and property manager. 4 bedroom and bathroom layout was awkward but we worked it out. Well equipped kitchen . Overall great time ."
Waterfront Anchor House with Boat Basin & Ramp!
Ocean Front - Private 56' Dock
Terrace/patio

Ocean Front - Private 56' Dock

9.8 out of 10, Exceptional, (137)
"Love the location and property. Going to make it my go to location in the lower keys. Property fully equipped. Beds super comfortable. Just the right size for 4 adults. In a very nice community. Gate staff very friendly and helpful. Thank you. "
The price is AED 1,258
AED 2,940 total
includes taxes & fees
17 Mar - 18 Mar
Ocean Front - Private 56' Dock
**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

9.0 out of 10, Wonderful, (10)
"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
Canal front home @ Venture Out Resort in the Florida Keys!
Exterior

Canal front home @ Venture Out Resort in the Florida Keys!

9.4 out of 10, Exceptional, (36)
"house was clean and easily accessible. Was suppose to have bikes to use but tires were flat. Really wanted to use them."
Canal front home @ Venture Out Resort in the Florida Keys!
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

Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (171)
"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."
The price is AED 826
AED 1,515 total
includes taxes & fees
28 Mar - 29 Mar
Direct Oceanfront Cottage-Sunrise View- #2,
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, (132)
"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!
Cottage with Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (135)
"Very nice"
The price is AED 1,010
AED 1,748 total
includes taxes & fees
15 Mar - 16 Mar
Cottage with Pool and Dockage, just minutes to 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.