Sugarloaf Key Vacation Rentals

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Our top choices for Sugarloaf Key vacation homes

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
The price is CA $568
CA $1,141 total
includes taxes & fees
May 24 - May 25
Starlight Serenity - Hideaway w Stunning Views

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
10.0 out of 10, Exceptional, (11 reviews)
"The location of the home is great, beautiful and peaceful.Enjoyed the pool."
United States
Rachel N.
The price is CA $1,285
CA $2,369 total
includes taxes & fees
May 21 - May 22
Private and Exclusive Beach Getaway

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
The price is CA $794
CA $1,651 total
includes taxes & fees
May 26 - May 27
Private and Exclusive Florida Keys Getaway

The Hemingway - Beach Houses Key West

The Hemingway - Beach Houses Key West
Upper Sugarloaf Key
9.6 out of 10, Exceptional, (8 reviews)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
United States
Brian K.
The price is CA $1,262
CA $2,344 total
includes taxes & fees
Jun 2 - Jun 3
The Hemingway - Beach Houses Key West

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 CA $370
CA $948 total
includes taxes & fees
May 24 - May 25
Starlight Serenity - Hideaway with Stunning Views

Private and Exclusive Beach Getaway

Private and Exclusive Beach Getaway
Sugarloaf Key
8.0 out of 10, Very good, (2 reviews)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
United States
Samat S.
The price is CA $2,215
CA $3,768 total
includes taxes & fees
Jun 9 - Jun 10
Private and Exclusive Beach Getaway

The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is CA $1,047
CA $2,637 total
includes taxes & fees
May 21 - May 22
The Fairhaven House at Solaire Lunara Bay

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 CA $325
CA $879 total
includes taxes & fees
May 24 - May 25
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (37 reviews)
"Great house and location. We have found our rental for our yearly stay in Key West. "
United States
Elizabeth F.
The price is CA $411
CA $843 total
includes taxes & fees
Jun 2 - Jun 3
Paradise found

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

One of the very few beach houses with a daily, rental license in the Keys.
Summerland Key
8.8 out of 10, Excellent, (69 reviews)
"Such a beautiful home, the view is to die for. It could definitely use some upgrades like the washer and dryer, but can’t beat the location and the fact that its beachfront. "
United States
LIZ
The price is CA $823
CA $1,955 total
includes taxes & fees
Jun 10 - Jun 11
One of the very few beach houses with a daily, rental license in the Keys.

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 CA $481
CA $941 total
includes taxes & fees
May 25 - May 26
Spanish Queen @Venture Out, 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 CA $346
CA $927 total
includes taxes & fees
May 21 - May 22
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Floralee House at Lunara Bay

Floralee House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (10 reviews)
"Wonderful host, smooth check in, very timely communications, great amenities, highly recommend it"
Canada
Marc D.
The price is CA $823
CA $2,346 total
includes taxes & fees
May 21 - May 22
Floralee House at Lunara Bay

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

SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (108 reviews)
"Had everything we needed. "
United States
Moriah W.
The price is CA $273
CA $683 total
includes taxes & fees
May 24 - May 25
SAVE BIG $$$ MAY!! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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 CA $433
CA $898 total
includes taxes & fees
Jun 3 - Jun 4
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveller
The price is CA $823
CA $1,997 total
includes taxes & fees
May 21 - May 22
Capmar House at Lunara Bay

Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is CA $1,263
CA $2,671 total
includes taxes & fees
May 28 - May 29
Mirador House by Brightwild Pool Dock

Altair House at Lunara Bay

Altair House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (13 reviews)
"host was very kind to let us do early check-in and late check out. The house is great, was very clean, everything was working perfectly."
United States
Esteban M.
The price is CA $823
CA $2,346 total
includes taxes & fees
May 21 - May 22
Altair House at Lunara Bay

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (42 reviews)
"Had to book here last minute due to first booking being canceled night before check-in! What a great experience this was. Host was very easy to deal with and would respond back very quickly. Even willing to let is get in a little early due to our situation. Glad we booked here! ALSO the house and property are great! Very well maintained and clean! "
United States
Matt P.
The price is CA $823
CA $2,186 total
includes taxes & fees
May 27 - May 28
Suncoast House at Lunara Bay

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

SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (89 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
The price is CA $260
CA $666 total
includes taxes & fees
May 21 - May 22
SAVE BIG $$$ MAY!!! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
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 Sugarloaf Key Hotel Reviews

Find out more about Sugarloaf Key

Sugarloaf Key Vacation Homes information

Number of reviews
655
Accommodation
821 Vacation Homes
Lowest Price
CA $666
Highest Price
CA $3,768

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