Vacation rentals in Upper Sugarloaf Key

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Top-rated vacation rentals in Upper Sugarloaf Key

Guests agree: these stays are highly rated for location, cleanliness, and more.

Superhost
Cottage in Cudjoe Key
ATLANTIS...Ocean Front Cottage Retreat!
ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!
Feb 7 – 14
$759 per night
4.92 out of 5 average rating, 130 reviews
Guest favorite
Home in Cudjoe Key
Conch Cabana in Paradise 23 miles outside Key West
Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Residential Condominium! Is located on a 60' wide canal, our Dock is 35 feet. With fish clean table, cleats, bumpers and patio table with 4 chairs. Two porches for outdoor enjoyment over looking the water and front yard. Just a few steps from the pool, hot tub (please be aware that they can close the pool and hot tub for emergency/ regular maintenance without any notice), marina, store, rec hall, tennis. And 23 miles from Key West!
May 28 – Jun 4
$264 per night
4.94 out of 5 average rating, 18 reviews
Superhost
Tiny home in Big Pine Key
Breezy pines 28 foot 5th wheel trailer .
Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.
Oct 3 – 10
$100 per night
4.8 out of 5 average rating, 88 reviews

Popular amenities for Upper Sugarloaf Key vacation rentals

Other great vacation rentals in Upper Sugarloaf Key

Superhost
Home in Summerland Key
Bungalows at Sugarloaf Beach - Little Hammock
Feb 25 – Mar 4
$396 per night
4.8 out of 5 average rating, 5 reviews
Guest favorite
Cottage in Cudjoe Key
King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
Jan 6 – 13
$499 per night
4.9 out of 5 average rating, 73 reviews
Superhost
Home in Cudjoe Key
Latitudes-Ocean Front Pool
Sep 14 – 21
$594 per night
5.0 out of 5 average rating, 3 reviews
Superhost
Home in Cudjoe Key
Relaxing Home in the Keys
Jan 2 – 9
$195 per night
4.84 out of 5 average rating, 38 reviews
Superhost
Home in Cudjoe Key
Venture Out -Million Dollar Island Resort
Apr 13 – 20
$228 per night
5.0 out of 5 average rating, 3 reviews
Guest favorite
Vacation home in Cudjoe Key
Beautiful Cottage & Amenities in Gated Community
Nov 27 – Dec 4
$294 per night
5.0 out of 5 average rating, 29 reviews
Superhost
Home in Cudjoe Key
Sailfish Haven
Aug 26 – Sep 2
$265 per night
4.83 out of 5 average rating, 6 reviews
Superhost
Cottage in Cudjoe Key
Turtle Cove Views @ Venture Out - Waterfront
Jul 30 – Aug 6
$555 per night
4.94 out of 5 average rating, 51 reviews
Guest favorite
Home in Marathon
The Gulf Cottage at Marathon Key
May 1 – 8
$110 per night
4.97 out of 5 average rating, 30 reviews
Superhost
Home in Cudjoe Key
Little gem in a safe resort with amenities
Sep 17 – 24
$238 per night
4.81 out of 5 average rating, 16 reviews
Guest favorite
Camper/RV in Big Pine Key
Delightful 1 bedroom camper with pool
Jun 11 – 18
$153 per night
4.94 out of 5 average rating, 35 reviews
Superhost
Home in Cudjoe Key
Cozy 2 br/2 bath home in Cudjoe
Sep 5 – 12
$212 per night
4.95 out of 5 average rating, 21 reviews

Destinations to explore