Holiday rentals in Upper Sugarloaf Key
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Top-rated holiday rentals in Upper Sugarloaf Key
Guests agree: these stays are highly rated for location, cleanliness and more.
Cottage in Cudjoe Key
4.92 out of 5 average rating, 130 reviewsATLANTIS...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!
28 Dec – 4 Jan
Home in Cudjoe Key
4.94 out of 5 average rating, 18 reviewsConch 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!
7–14 Jun
Tiny home in Big Pine Key
4.8 out of 5 average rating, 88 reviewsBreezy 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.
16–23 Oct
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Upper Sugarloaf Key holiday rentals
Other great holiday rentals in Upper Sugarloaf Key
Home in Cudjoe Key
4.83 out of 5 average rating, 24 reviewsKeys Island Villa - Venture Out Home 354
19–26 Dec
Cottage in Cudjoe Key
4.91 out of 5 average rating, 75 reviewsKing Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks
24 Feb – 3 Mar
Home in Cudjoe Key
5.0 out of 5 average rating, 5 reviewsVenture Out -Million Dollar Island Resort
23–30 Nov
Guest suite in Key Colony Beach
4.99 out of 5 average rating, 81 reviewsTurtle-By-The-Sea: the Best Deal in KCB!
3–10 May
Campervan/Motorhome in Big Pine Key
4.91 out of 5 average rating, 34 reviewsHaving fun in the lower Keys
31 Jul – 7 Aug
Home in Marathon
4.97 out of 5 average rating, 31 reviewsBeach House, Private Pool & Dock, Gulf Sunset view
9–16 Nov
Apartment in Key West
4.99 out of 5 average rating, 83 reviewsHidden Beach Duplex, Best Place in Key West
2–9 Aug
Holiday home in Cudjoe Key
5.0 out of 5 average rating, 30 reviewsBeautiful Cottage & Amenities in Gated Community
23–30 Aug
Home in Key Largo
5.0 out of 5 average rating, 44 reviewsThe Paradise 2
2–9 Feb
Home in Marathon
5.0 out of 5 average rating, 8 reviewsMillion Dollar View
12–19 Oct
Place to stay in Cudjoe Key
5.0 out of 5 average rating, 3 reviewsKeysie Does It @ Cudjoe Key - Home in Waterfront
9–16 Sep
Home in Cudjoe Key
4.96 out of 5 average rating, 23 reviewsCozy 2 br/2 bath home in Cudjoe
22–29 Nov
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