Family-friendly holiday rentals in Sugarloaf Key
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Sugarloaf Key
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Sugarloaf Key family-friendly rentals
Family-friendly home rentals with a hot tub
Townhouse in Marathon
4.83 out of 5 average rating, 123 reviewsPlunge Pool Villa on Blue Water Lagoon
18–25 Nov
Home in Cudjoe Key
4.6 out of 5 average rating, 148 reviewsOcean Front Home in Great Location
1–8 Sep
Home in Key Colony Beach
5.0 out of 5 average rating, 33 reviewsFlorida Keys Retreat with Cabana Club.
1–8 Mar
Apartment in Key West
4.76 out of 5 average rating, 270 reviewsAffordable Beachfront Luxury Condo Sleeps 6
29 Aug – 5 Sep
Apartment in Key West
4.95 out of 5 average rating, 38 reviewsSmooth Sailing @ The Beach - Oceanside Condo
5–12 Dec
Home in Key West
4.78 out of 5 average rating, 74 reviewsHistoric Key West - Conch House - Sleeps 5
21–28 Aug
Apartment in Key West
4.78 out of 5 average rating, 27 reviewsHenry's Piece of Paradise On The Ocean In Key West
15–22 Dec
Home in Key West
4.83 out of 5 average rating, 23 reviewsCasablanca Too ~ Chicly Updated Home With Hot Tub
25 Sep – 2 Oct
Family- and pet-friendly home rentals
Townhouse in Key West
4.88 out of 5 average rating, 75 reviews3/3 Tropical Key West Home Get Away
13–20 Aug
Campsite in Big Pine Key
4.73 out of 5 average rating, 108 reviewsBring Your Own RV! Our Lot Your RV 6
28 Oct – 4 Nov
Home in Marathon
4.88 out of 5 average rating, 34 reviewsSunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
9–16 Nov
Townhouse in Marathon
4.94 out of 5 average rating, 33 reviewsWaterfront luxury Villa (59) with sunset views and boat slip
10–17 Apr
Home in Summerland Key
Family Retreat
2–9 Nov
Home in Key West
4.83 out of 5 average rating, 315 reviewsCasa Cristol - Family Friendly Classic KW Charm
19–26 Apr
Home in Summerland Key
4.7 out of 5 average rating, 90 reviews2 Bedroom Sunset Bungalow
26 Oct – 2 Nov
Home in Marathon
4.92 out of 5 average rating, 48 reviewsCastaway 2/2 w/ 50` Ft. Dock on the Atlantic
13–20 Sep
Family-friendly home rentals with a pool
Home in Key Colony Beach
4.96 out of 5 average rating, 135 reviewsBeautiful open plan remodeled home in Key Colony
17–24 Aug
Home in Key Colony Beach
4.9 out of 5 average rating, 133 reviewsTiki Time 2
15–22 Aug
Home in Marathon
4.87 out of 5 average rating, 54 reviewsBeautiful Beachfront Home w/ Pool/Tiki/Dock
7–14 Sep
Campervan/Motorhome in Big Pine Key
4.71 out of 5 average rating, 113 reviewsTropical Caribbean Wonderland
26 Sep – 3 Oct
Apartment in Marathon
4.76 out of 5 average rating, 63 reviewsBeach Hut: beach front, heated pool.
11–18 Nov
Townhouse in Marathon
4.96 out of 5 average rating, 74 reviewsLife in Paradise with Boat Slip in Coral Lagoon
12–19 Apr
Apartment in Key West
4.87 out of 5 average rating, 168 reviewsTropical Old Town Bungalow
21–28 Nov
Villa in Marathon
4.87 out of 5 average rating, 107 reviewsDuck Key 4 BR Villa Dock Behind & Cabana Club
20–27 Aug
Destinations to explore
- Key West Holiday rentals
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- Family-friendly rentals United States
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