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Check prices for these dates

In two weeks
5 Jun - 7 Jun
In two months
17 Jul - 19 Jul
In three months
14 Aug - 16 Aug
In four months
11 Sep - 13 Sep

Our top choices for Summerland Key vacation homes

Beach

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 AED 868
AED 2,350 total
includes taxes & fees
24 May - 25 May
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & 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 AED 817
AED 2,316 total
includes taxes & fees
26 May - 27 May
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Exterior

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (89 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is AED 694
AED 1,785 total
includes taxes & fees
25 May - 26 May
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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 AED 771
AED 2,282 total
includes taxes & fees
29 May - 30 May
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near 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 AED 656
AED 2,108 total
includes taxes & fees
24 May - 25 May
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
A heated pool

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)
"Close to Key West. Would stay there again!!"
United States
elisa b.
The price is AED 733
AED 2,227 total
includes taxes & fees
25 May - 26 May
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key
Exterior

SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is AED 731
AED 1,834 total
includes taxes & fees
25 May - 26 May
SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool

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 AED 964
AED 2,495 total
includes taxes & fees
22 May - 23 May
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
A heated pool

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (13 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AED 771
AED 2,271 total
includes taxes & fees
2 Jun - 3 Jun
Island Time #110 Ocean Views - Cudjoe Key
Terrace/patio

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (8 reviews)
"Gorgeous place! Had an excellent time. Very clean and easy check-in/out process. Highly recommend!"
United States
Susan B.
The price is AED 1,639
AED 3,376 total
includes taxes & fees
25 May - 26 May
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
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, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is AED 790
AED 1,956 total
includes taxes & fees
10 Jun - 11 Jun
Kelly's Kabin - Adorable Private Summerland Key Cottage
A heated pool

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"Great place! Perfect location"
United States
Troy B.
The price is AED 868
AED 2,387 total
includes taxes & fees
28 May - 29 May
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key
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 AED 964
AED 2,495 total
includes taxes & fees
22 May - 23 May
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Property grounds

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

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (157 reviews)
"Great place with beautiful views, house could use some TLC so the trade out is location and outdoor space with nice yard and very peaceful. "
United States
Peggy H.
The price is AED 1,074
AED 2,292 total
includes taxes & fees
2 Jun - 3 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Beach

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key

Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key
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 AED 713
AED 2,206 total
includes taxes & fees
25 May - 26 May
Little Piece of Paradise #233 - 35' Seawall - Cudjoe Key
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, (25 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 AED 1,286
AED 2,503 total
includes taxes & fees
2 Jun - 3 Jun
Spanish Queen @Venture Out, Cudjoe Key
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, (168 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 AED 1,157
AED 2,400 total
includes taxes & fees
3 Jun - 4 Jun
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
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)
"Online photos did not match the house. You entered the house through one of the bedrooms. So privacy for those staying in that room did not exist. The extra you pay when checking in for the club amenities was not worth the expense. "
United States
Seth
The price is AED 750
AED 1,689 total
includes taxes & fees
1 Jun - 2 Jun
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!
Terrace/patio

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 AED 988
AED 2,505 total
includes taxes & fees
24 May - 25 May
Starlight Serenity - Hideaway with Stunning Views
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, (2 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is AED 964
AED 2,495 total
includes taxes & fees
22 May - 23 May
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
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

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

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

10/10 Excellent
"This property was clean and comfortable and had everything we needed. The best part was access to the Kayaks, multiple bikes, beach umbrellas, chairs, towels and fishing gear. The appliances were new and everything worked great. There are (2) bedrooms and the beds are a bit small but they were comfortable."
William V. 3-night trip
Posted 16 hours ago
Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security