View To Old Bahia Honda Bridge, Part Of The Florida Keys Overseas Heritage Trails, From West Summerland Key On A Sunny Autumn Day With A Clear Blue Sky And A Few Clouds

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

Our top choices for Summerland Key holiday homes

Exterior

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, (171 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$2,743
HK$5,437 total
includes taxes & fees
5 Jul - 6 Jul
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
A heated pool

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$4,734 total
includes taxes & fees
15 Jun - 16 Jun
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
A heated pool

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$1,234
HK$4,296 total
includes taxes & fees
10 Jun - 11 Jun
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior

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

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (90 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is HK$1,168
HK$3,378 total
includes taxes & fees
10 Jun - 11 Jun
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Fridge, microwave, oven, stovetop

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$3,913 total
includes taxes & fees
13 Jun - 14 Jun
Kelly's Kabin - Adorable Private Summerland Key Cottage
A heated pool

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$1,440
HK$4,606 total
includes taxes & fees
11 Jun - 12 Jun
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior detail

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$1,643
HK$4,812 total
includes taxes & fees
17 Jun - 18 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Exterior

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

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is HK$1,167
HK$3,400 total
includes taxes & fees
20 Jun - 21 Jun
SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool

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$1,851
HK$5,069 total
includes taxes & fees
10 Jun - 11 Jun
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Beach

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$1,646
HK$4,806 total
includes taxes & fees
10 Jun - 11 Jun
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A heated pool

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, (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$4,604 total
includes taxes & fees
22 Jun - 23 Jun
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
A heated pool

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$1,645
HK$4,804 total
includes taxes & fees
10 Jun - 11 Jun
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Exterior

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$4,575 total
includes taxes & fees
10 Jun - 11 Jun
Waterfront with Boat Dock, Heated Pool, Amenities, Waterfront Home, Heated Pool, Boat Dock
A heated pool

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$5,647 total
includes taxes & fees
17 Jun - 18 Jun
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Beach

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, (14 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is HK$1,645
HK$4,812 total
includes taxes & fees
22 Jun - 23 Jun
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Outdoor pool, a heated pool

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$3,580 total
includes taxes & fees
10 Jun - 11 Jun
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Outdoor pool, a heated pool

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$2,939
HK$5,538 total
includes taxes & fees
10 Jul - 11 Jul
Spanish Queen @Venture Out, Cudjoe Key
Beach

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$4,804 total
includes taxes & fees
10 Jun - 11 Jun
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Beach

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
8.0 out of 10, Very good, (1 review)
"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...
United States
Pauline Y.
The price is HK$1,440
HK$4,573 total
includes taxes & fees
22 Jun - 23 Jun
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Dining

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$3,003
HK$7,088 total
includes taxes & fees
21 Jun - 22 Jun
Post Card Point #319 - Ocean Views!
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

Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"A classic property in the old style of the lower keys from the 70s. Even though rooms are a bit dated, they are very clean with a great floating dock to moor your boat. Nice marina right next door with a good ramp. If your game is to fish the back country this is your place."
Matthew 3-night trip
Posted 3 hours ago
Sugar Loaf Lodge

Find out more about Summerland Key

Summerland Key Vacation Homes information

Number of reviews
661
Accommodation
380 Vacation Homes
Lowest Price
HK$3,378
Highest Price
HK$7,088

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