We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows:
Internet Explorer
,
Mozilla Firefox
,
Google Chrome
. Mac:
Safari
.
Flights
Vacation Rentals
Restaurants
Things to do
Skip to main content
Discover
Trips
Review
More
CAD
Sign in
Sugarloaf
Hotels
Things to Do
Restaurants
Flights
Vacation Rentals
Cruises
Rental Cars
Forums
Inbox
See all
Sign in
to get trip updates and message other travellers.
Vacation Rentals in Sugarloaf, FL
Vacation Rentals
USA
Florida (FL)
Florida Keys
Vacation Rentals in Sugarloaf, FL
Search
Owner log in
Sugarloaf
Vacation Rentals
Destination
Check In
Check Out
Guests
2 Guests
Map
Tripadvisor Sort
Revenue impacts this sort order.
Learn more
Bedrooms
Any
Bathrooms
Any
Amenities
Internet or Wifi (43)
Air Conditioning (42)
Washer/Dryer (39)
Grill (38)
Show all
Suitability
Kid friendly (43)
Pet friendly (26)
Elder access (1)
Smoking allowed (1)
Show more
Property type
Vacation Rental House (44)
Condominium/Apartment (0)
Cabin Vacation Rental (0)
Private Room (0)
Show more
Distinctive Features
Waterfront (30)
Boat Available (2)
Private Chef (0)
Private Beach (0)
Show all
Distance from
5 km
Sugarloaf Key Bat Tower
Skydive Key West
Native Guidance
Show all
44 rentals
in Sugarloaf.
Palms Resort at Sugarloaf Beach - Main House
2 reviews
Holiday Rental House
View on map
5 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
BRAND NEW WATERFRONT 3/2
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Bungalows at Sugarloaf Beach - The Palm.
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Amazing Waterfront Home with Fabulous Pool and Sunset Views
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Luxury Waterfront Home with Gorgeous Pool, Tiki Bar and Sunsets
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Open Water Views, Sunsets and 2 New Beautiful Pools Create Your Island Oasis
Holiday Rental House
View on map
7 bedrooms
7 bathrooms
Sleeps 17
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Cassie’s Paradise - Luxury Vacation Rental in the Florida Keys
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Oceanside, pet friendly, 5/3 smart home with paddle equip.-SUPs, kayaks & canoe
Holiday Rental House
View on map
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Bungalows at Sugarloaf Beach - The Lighthouse
Holiday Rental House
View on map
2 bedrooms
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The following properties within 32 kms of Sugarloaf match all your filters:
The Sunset Cottage of Pelico Palms
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Tropical Serenity in Sugarloaf: Waterfront 2BR Paradise, Pool, Tiki, Dockage
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful POOL3/2 Sleeps 8. ALL ROOMS Waterfront
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Sugarloaf Serenity | Spacious, pet-friendly waterfront retreat on Sugarloaf Key
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Bungalows at Sugarloaf Beach - Mi Azucar
Holiday Rental House
View on map
2 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Palms Resort at Sugarloaf Beach - Guest House
5 reviews
Holiday Rental House
View on map
2 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Bungalows at Sugarloaf Beach - The Hemingway
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Summer Sunsets are waiting for you !!
Holiday Rental House
View on map
5 bedrooms
3 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Blue Wahoo-Perfect Keys Getaway
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
**BLUE HORIZON * SUGARLOAF SHORES** Waterfront Home & Pool + LAST KEY SERVICES…
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Charming Canal Front 3-bedroom house in Sugarloaf Key
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
17ft Action craft flats boat included
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
**CASSIE’S PARADISE * SUGARLOAF SHORES** Waterfront Mansion & Pool + LAST KEY SE
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Sunset Paradise: 4 bedroom/5 bathroom, oceanfront with pool
Holiday Rental House
View on map
4 bedrooms
5 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Dulces Suenos / Waterfront luxury at a DISCOUNT! Why rent a home on a canal?
3 reviews
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
PARADISE FOUND on Sugarloaf Key! Please call *******-8105 for the latest updates
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Family Friendly House In Paradise
Holiday Rental House
View on map
5 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Sugarloaf Bay Retreat: Tropical Canal Front 3BR Home, Private Pool, Open Water
Holiday Rental House
View on map
3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Beautiful spacious 4/4 on pristine swim canal. 20 min to key west
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Paradise Point: Your Luxurious Waterfront Getaway with Pool, Tiki, Dockage, and
5 reviews
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Bayside Beauty: Tropical Paradise 3BR Home, Panoramic Open Water Views, Private
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
THE BLACK MARLIN - 3 BEDROOM / 2.5 BATHROOM WITH POOL & TIKI HUT
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Modular House on beautiful Sugarloaf Key. Fabulous boating on your doorstep
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The Banana Cabana, Canal Front Home Sugarloaf Key Mm 17
9 reviews
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
South Point Sunset - Florida Keys waterfront
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Ocean Front Luxury Vacation Rental Near Key West
Holiday Rental House
View on map
4 bedrooms
5 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Sugarloaf Key Home With Beach, Dock and Canal!
11 reviews
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Waterfront Sugarloaf Key Home
Holiday Rental House
View on map
2 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Sugarloaf Sunrise
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
The Perfect Catch: Family Fun and Boater's Bliss in the Keys!
Holiday Rental House
View on map
4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Bungalows at Sugarloaf Beach - Hammock House
Holiday Rental House
View on map
3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Sugarloaf Shores Wide Canal 3/3 Waterfront w/ 100 ft Seawall in Quite
Holiday Rental House
View on map
3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Holiday Rental House
View on map
1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool
Holiday Rental House
View on map
4 bedrooms
4 bathrooms
Sleeps 12
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
Green Turtle Oasis: Lovely 4BR Canal Front Home, Pool, Dockage, Tiki, Outdoor
Holiday Rental House
View on map
4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps
More info
Check-in
Check-out
Show Prices
As seen on
1
Showing results 1-44 of 44
Frequently Asked Questions about Sugarloaf
Do any vacation rentals in Sugarloaf have a pool?
Yes, here are some popular vacation rentals in Sugarloaf that have a pool:
Palms Resort at Sugarloaf Beach - Main House
BRAND NEW WATERFRONT 3/2
Bungalows at Sugarloaf Beach - The Palm.
See all vacation rentals with a pool in Sugarloaf on Tripadvisor
Do any vacation rentals in Sugarloaf have internet access?
Yes, here are some popular vacation rentals in Sugarloaf that have internet access:
Palms Resort at Sugarloaf Beach - Main House
BRAND NEW WATERFRONT 3/2
Bungalows at Sugarloaf Beach - The Palm.
See all vacation rentals in Sugarloaf on Tripadvisor
What are the best pet friendly rentals in Sugarloaf?
The best pet friendly rentals in Sugarloaf are:
Palms Resort at Sugarloaf Beach - Main House
BRAND NEW WATERFRONT 3/2
Bungalows at Sugarloaf Beach - The Palm.
See all pet friendly vacation rentals in Sugarloaf on Tripadvisor
What are some great rentals in Sugarloaf that are kid friendly?
Some of the most popular kid friendly rentals in Sugarloaf are:
Palms Resort at Sugarloaf Beach - Main House
BRAND NEW WATERFRONT 3/2
Bungalows at Sugarloaf Beach - The Palm.
See all kid friendly vacation rentals in Sugarloaf on Tripadvisor
Sugarloaf
Sugarloaf Tourism
Sugarloaf Hotels
Sugarloaf Vacation Rentals
Flights to Sugarloaf
Restaurants near Sugarloaf
Sugarloaf Attractions
Sugarloaf Travel Forum
Sugarloaf Photos
Sugarloaf Map
Sugarloaf Guide
Hotels
All Sugarloaf Hotels
Sugarloaf Hotel Deals
By Hotel Class
5-stars Hotels in Sugarloaf
4-stars Hotels in Sugarloaf
3-stars Hotels in Sugarloaf
Popular Sugarloaf Categories
Sugarloaf Pet Friendly Campsites
Sugarloaf Campsites
Near Airports
Hotels near (EYW) Key West Intl Airport
Things to Do
Restaurants
Flights
Vacation Rentals
Places of Interest
Vacation Rentals near Florida Keys Jet Ski Rentals
Airports
Vacation Rentals near Key West Intl Airport
Travel Stories
Cruises
Rental Cars
More
Tours
Add a Place
Travel Forum
Airlines
Travellers' Choice
Help Centre
Travel Stories