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Our top choices for Summerland Key holiday homes

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

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (170 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is HK$2,468
HK$5,119 total
includes taxes & fees
9 Jun - 10 Jun
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

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

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is HK$1,645
HK$4,757 total
includes taxes & fees
8 Jun - 9 Jun
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

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 HK$1,398
HK$4,527 total
includes taxes & fees
8 Jun - 9 Jun
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (90 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is HK$1,167
HK$3,400 total
includes taxes & fees
10 Jun - 11 Jun
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (125 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is HK$1,516
HK$3,935 total
includes taxes & fees
13 Jun - 14 Jun
Kelly's Kabin - Adorable Private Summerland Key Cottage

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (4 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is HK$1,671
HK$4,852 total
includes taxes & fees
15 Jun - 16 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

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 HK$1,563
HK$4,767 total
includes taxes & fees
11 Jun - 12 Jun
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

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

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is HK$1,167
HK$3,416 total
includes taxes & fees
15 Jun - 16 Jun
SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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, (3 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is HK$2,056
HK$5,353 total
includes taxes & fees
9 Jun - 10 Jun
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

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
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is HK$1,645
HK$4,844 total
includes taxes & fees
8 Jun - 9 Jun
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

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 HK$1,769
HK$5,022 total
includes taxes & fees
21 Jun - 22 Jun
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 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 HK$1,481
HK$4,635 total
includes taxes & fees
8 Jun - 9 Jun
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (29 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is HK$2,262
HK$5,624 total
includes taxes & fees
8 Jun - 9 Jun
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

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
7.8 out of 10, Good, (20 reviews)
"Everything was perfect location house amenities Really enjoyed our time there"
United States
Matt S.
The price is HK$1,601
HK$3,602 total
includes taxes & fees
9 Jun - 10 Jun
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Waterfront with Boat Dock, Heated Pool, Amenities, Waterfront Home, Heated Pool, Boat Dock

Waterfront with Boat Dock, Heated Pool, Amenities, Waterfront Home, Heated Pool, Boat Dock
Cudjoe Key
The price is HK$1,712
HK$4,605 total
includes taxes & fees
10 Jun - 11 Jun
Waterfront with Boat Dock, Heated Pool, Amenities, Waterfront Home, Heated Pool, Boat Dock

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is HK$2,742
HK$5,362 total
includes taxes & fees
29 Jun - 30 Jun
Spanish Queen @Venture Out, Cudjoe Key

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Cudjoe Key
8.0 out of 10, Very good, (1 review)
"It was a short trip but we enjoyed our stay! "
United States
Jennifer S.
The price is HK$1,645
HK$4,844 total
includes taxes & fees
8 Jun - 9 Jun
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

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 HK$2,648
HK$6,092 total
includes taxes & fees
21 Jun - 22 Jun
Starlight Serenity - Hideaway with Stunning Views

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (55 reviews)
"Great location in the complex and in the Keys themselves."
United States
Karl S.
The price is HK$3,085
HK$7,186 total
includes taxes & fees
21 Jun - 22 Jun
Post Card Point #319 - Ocean Views!

Mahi House #440 - 35' seawall

Mahi House #440 - 35' seawall
Cudjoe Key
9.0 out of 10, Wonderful, (4 reviews)
"Clean and excellent water access"
United States
Chris P.
The price is HK$1,851
HK$5,130 total
includes taxes & fees
8 Jun - 9 Jun
Mahi House #440 - 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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Top Summerland Key Hotel Reviews

Find out more about Summerland Key

Summerland Key Vacation Homes information

Number of reviews
650
Accommodation
380 Vacation Homes
Lowest Price
HK$3,400
Highest Price
HK$7,186

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