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.

Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 130 reviews

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!

28 Dec – 4 Jan

€ 771 per night
Guest favourite

Home in Cudjoe Key

4.94 out of 5 average rating, 18 reviews

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!

7–14 Jun

€ 351 per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

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.

16–23 Oct

€ 128 per night

Popular amenities for Upper Sugarloaf Key holiday rentals

Other great holiday rentals in Upper Sugarloaf Key

Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 24 reviews

Keys Island Villa - Venture Out Home 354

19–26 Dec

€ 527 per night
Guest favourite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 75 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

24 Feb – 3 Mar

€ 878 per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 5 reviews

Venture Out -Million Dollar Island Resort

23–30 Nov

€ 355 per night
Guest favourite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 81 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

3–10 May

€ 197 per night
Guest favourite

Campervan/Motorhome in Big Pine Key

4.91 out of 5 average rating, 34 reviews

Having fun in the lower Keys

31 Jul – 7 Aug

€ 181 per night
Guest favourite

Home in Marathon

4.97 out of 5 average rating, 31 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

9–16 Nov

€ 617 per night
Guest favourite

Apartment in Key West

4.99 out of 5 average rating, 83 reviews

Hidden Beach Duplex, Best Place in Key West

2–9 Aug

€ 684 per night
Guest favourite

Holiday home in Cudjoe Key

5.0 out of 5 average rating, 30 reviews

Beautiful Cottage & Amenities in Gated Community

23–30 Aug

€ 380 per night
Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 44 reviews

The Paradise 2

2–9 Feb

€ 361 per night
Guest favourite

Home in Marathon

5.0 out of 5 average rating, 8 reviews

Million Dollar View

12–19 Oct

€ 871 per night
Superhost

Place to stay in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Keysie Does It @ Cudjoe Key - Home in Waterfront

9–16 Sep

€ 387 per night
Superhost

Home in Cudjoe Key

4.96 out of 5 average rating, 23 reviews

Cozy 2 br/2 bath home in Cudjoe

22–29 Nov

€ 282 per night

Destinations to explore