Vacation Rentals & House Rentals in Sugarloaf Key

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580 house rentals

44

Large, dog-friendly home on three secluded acres w/ balconies, deck, views

Florida Keys / Sugarloaf Key

Sugarloaf Key house

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$173

Price per night from

$173

24

Upscale 3BR w/ Chef’s Kitchen, Private Pool & Central Location

Florida Keys / Sugarloaf Key

Sugarloaf Key house

3 6 30 nights min

  • 3 bedrooms
  • sleeps 6
  • 30 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$309

Price per night from

$309

30

Relax on historic inn's top floor - shared pool & semi-private deck!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$46

Price per night from

$46

23

Charming attic studio suite in historic inn w/ a shared pool & a great location!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$40

Price per night from

$40

(1) Very Good 

24

Lovely room in historic bed & breakfast w/ shared pool & a semi-private balcony

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$40

Price per night from

$40

29

Cozy ground-floor suite in historic home w/ shared pool - close to boardwalk!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$46

Price per night from

$46

36

Charming main-floor suite in historic bed & breakfast - shared swimming pool!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$46

Price per night from

$46

29

Cozy, tropical getaway w/ shared pool - close to shopping and restaurants

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$60

Price per night from

$60

(1) Excellent 

29

Enjoy a shared pool & a great location at this main-floor bed & breakfast suite!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$60

Price per night from

$60

28

Quiet ground-floor suite in historic inn - shared pool & great location!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$59

Price per night from

$59

24

Spacious suite w/ semi-private porch, a shared pool, & lots of charm!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$60

Price per night from

$60

(3) Average 

25

Historic vacation rental with a private pool - dog-friendly!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$140

Price per night from

$140

(3) Very Good 

26

Romantic & elegant studio-style cottage w/ private hot tub - dog-friendly!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$60

Price per night from

$60

(4) Very Good 

27

Dog-friendly studio w/ private deck & hot tub - 1 block to Duval St!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 4 min stay varies

  • Studio
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$59

Price per night from

$59

(14) Excellent 

44

Dog-friendly, colorful cottages w/ pool & hot tub in a fabulous location!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

5 16 min stay varies

  • 5 bedrooms
  • sleeps 16
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Love Key West” We had a group of 10 people and we stayed at almost Southernmost Retreat. The property consisted of 2 homes that were connected with a pool and hot tub. The property was fantastic. Great location and the property was well kept and ver
…see more

Price per night from

$534

Price per night from

$534

(1) Excellent 

24

Restored historic home w/ private pool & reserved off-street parking - Dogs OK!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$564

Price per night from

$564

(12) Very Good 

27

Charming cottage w/ private hot tub - 1 block from Duval, dogs OK!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning
“Great location but lacks parking” This house is a clean, comfortable cottage in a terrific location. Great size for two couples or a small family. It is in walking distance to anywhere in old-town, and conveniently placed for travel via us 1 to othe
…see more

Price per night from

$295

Price per night from

$295

(8) Very Good 

30

Colorful, dog-friendly cottage w/ private pool & all the comforts of home

Florida Keys / Sugarloaf Key

Sugarloaf Key house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Fantastic, wonderful experience.” Great location, in the center of KeyWest. Parked the car and walked,biked,trollied everywhere. Beautiful color scheme, every room was vibrant with a South Florida palat. Fantastic new kitchen and pool. Spent many hour
…see more

Price per night from

$144

Price per night from

$144

(5) Very Good 

29

Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool

Florida Keys / Sugarloaf Key

Sugarloaf Key house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$553

Price per night from

$553

27

Dog-friendly studio in historic building w/ shared pool - beach nearby!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$40

Price per night from

$40

(1)  

26

Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$198

Price per night from

$198

(3) Very Good 

44

Two rustic cottages w/ private hot tubs & private parking - dogs OK

Florida Keys / Sugarloaf Key

Sugarloaf Key house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning
“Awesome place to stay!!!” The entire booking, service while there, and contact with the rental agency was great. Perfect area...2 short blocks off Duval St. and within walking to various stores and restaurants. Even though was Spring Break time it w
…see more

Price per night from

$436

Price per night from

$436

(37) Very Good 

32

Cozy cottage w/ private hot tub, tranquil garden & parking - dogs OK!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning
“helpful and courteous” The service we received was excellent. The check in was easy to find and the help was very friendly and courteous. We loved the fact that we could leave our luggage between check in and check out time instead of having to carry
…see more

Price per night from

$69

Price per night from

$69

(21) Very Good 

25

Lovely, dog-friendly townhouse w/ private pool, full kitchen & beach access

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary
“Fabulous” We stayed at Island Oasis for Labor Day weekend 2008. The location is perfect! The house was EXTREMELY clean & well kept, furnishings & decor modern, the private pool is perfect, the rental agency was fabulous (helpful & friendly). We would
…see more

Price per night from

$423

Price per night from

$423

(1) Very Good 

29

Studio condo w/ shared courtyard & pool - walk to everything - dogs welcome!

Florida Keys / Sugarloaf Key

Sugarloaf Key studio

Studio 2 min stay varies

  • Studio
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$39

Price per night from

$39

(42) Very Good 

25

Island condo w/ balcony & great central location - beach nearby! Dogs OK!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning
“Awesome” The location Is close to the beach as well as restaurants and shops. It was clean and had everything we needed. Very cute. The veranda was nice to sit out in the morning and evening
…see more

Price per night from

$177

Price per night from

$177

37

Family Friendly condo w/ shared pool & hot tub, tennis courts, & parking space

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$185

Price per night from

$185

(2) Very Good 

24

Dog-friendly condo w/ scenic views, shared pool & hot tub, balcony & parking

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$186

Price per night from

$186

26

Charming house w/ private patio & hot tub - great central location, dogs OK

Florida Keys / Sugarloaf Key

Sugarloaf Key house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly
  • Car not necessary
  • Air conditioning

Price per night from

$235

Price per night from

$235

(2) Very Good 

24

Family friendly condo w/tennis, shared pool, hot tub, & private balcony- dogs ok

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$191

Price per night from

$191

27

Stylish condo with shared swimming pool moments from popular attractions!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$404

Price per night from

$404

38

Bright and sunny condo with patio, shared pool, and hot tub at Sunrise Suites

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$196

Price per night from

$196

26

Dog-friendly home w/ private pool - one block from Duval Street, near Old Town!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 4 28 nights min

  • 2 bedrooms
  • sleeps 4
  • 28 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$138

Price per night from

$138

24

Breezy condo w/ private patio, shared pool & hot tub, free parking - Dogs OK!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$185

Price per night from

$185

26

Dog-friendly Sunrise Suites condo w/ private balcony, views, shared pool/hot tub

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$196

Price per night from

$196

(1) Very Good 

26

Sunrise Suites condo w/water views, shared pool/hot tub, free parking- dogs ok!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$185

Price per night from

$185

25

Shared pool & hot tub, parking spot, balcony - one dog ok! Family friendly!

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$187

Price per night from

$187

24

Comfy dog-friendly condo w/ balcony, shared pool & hot tub, tennis, & parking

Florida Keys / Sugarloaf Key

Sugarloaf Key house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$199

Price per night from

$199