Family-friendly holiday rentals in Summerland Key
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Summerland 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 Summerland Key family-friendly rentals
Family-friendly home rentals with a hot tub
Flat in Key West
4.92 out of 5 average rating, 175 reviewsKW Luxury 2/2 Beachfront resort Tropical Oasis
31 Jan – 7 Feb
Apartment in Key West
4.85 out of 5 average rating, 106 reviewsMoonlight Paradise Upgraded Family oasis Tropical
24–31 Aug
Apartment in Tavernier
4.88 out of 5 average rating, 135 reviewsSpectacular 2 Bedroom with a beautiful ocean view.
7–14 Apr
Apartment in Tavernier
4.88 out of 5 average rating, 112 reviewsResort Getaway : Condo, Pool, Beach, Location
20–27 Sep
Flat in Tavernier
4.83 out of 5 average rating, 255 reviewsBreathtaking Oceanfront Views at Tropical Daze
3–10 Apr
Apartment in Tavernier
4.82 out of 5 average rating, 137 reviewsBright & Sunny Suite w/ Magnificent Ocean Views
26 Nov – 3 Dec
Apartment in Tavernier
4.83 out of 5 average rating, 178 reviewsToes in the Sand - 2 Bedroom Condo Sleeps 4
31 Oct – 7 Nov
Home in Key Colony Beach
5.0 out of 5 average rating, 33 reviewsFlorida Keys Retreat with Cabana Club.
19–26 Apr
Family- and pet-friendly home rentals
Townhouse in Marathon
4.83 out of 5 average rating, 122 reviewsPlunge Pool Villa on Blue Water Lagoon
22–29 Apr
Home in Cudjoe Key
4.6 out of 5 average rating, 148 reviewsOcean Front Home in Great Location
11–18 Sep
Townhouse in Key West
4.88 out of 5 average rating, 75 reviews3/3 Tropical Key West Home Get Away
9–16 May
Home in Marathon
4.88 out of 5 average rating, 33 reviewsSunset Catch Gulf Front, Pool, Dock, Kayaks, Fish
2–9 Nov
Home in Key West
4.98 out of 5 average rating, 48 reviewsPuerta Coralina @ Old Town - Cottage Near Duval
11–18 Jul
Campsite in Big Pine Key
4.73 out of 5 average rating, 108 reviewsBring Your Own RV! Our Lot Your RV 6
23–30 Oct
Home in Key West
4.83 out of 5 average rating, 23 reviewsCasablanca Too ~ Chicly Updated Home With Hot Tub
20–27 Jul
Townhouse in Marathon
4.94 out of 5 average rating, 33 reviewsWaterfront luxury Villa (59) with sunset views and boat slip
25 Oct – 1 Nov
Family-friendly home rentals with a pool
Home in Marathon
4.87 out of 5 average rating, 54 reviewsBeautiful Beachfront Home w/ Pool/Tiki/Dock
10–17 Dec
Campervan/Motorhome in Big Pine Key
4.71 out of 5 average rating, 113 reviewsTropical Caribbean Wonderland
15–22 Jan
Bungalow in Key West
4.94 out of 5 average rating, 96 reviewsFleming-O in Old Town close to Duval
24 Sep – 1 Oct
Townhouse in Marathon
4.96 out of 5 average rating, 73 reviewsLife in Paradise with Boat Slip in Coral Lagoon
14–21 Apr
Apartment in Marathon
4.76 out of 5 average rating, 63 reviewsBeach Hut: beach front, heated pool.
30 Jun – 7 Jul
Apartment in Islamorada
4.75 out of 5 average rating, 59 reviewsBayside Condo with Marina, Beach and Pool
28 Oct – 4 Nov
Villa in Marathon
4.88 out of 5 average rating, 196 reviewsCoral Lagoon Resort 3 BR W/ Dock Behind Villa
29 Dec – 5 Jan
Apartment in Key West
4.87 out of 5 average rating, 167 reviewsTropical Old Town Bungalow
6–13 Mar
Quick stats about holiday rentals that are family-friendly in Summerland Key
Total rentals
170 properties
Rentals with dedicated workspaces
70 properties have a dedicated workspace
Rentals with a pool
110 properties have a pool
Pet-friendly rentals
60 properties allow pets
Total number of reviews
3.1K reviews
Nightly prices starting at
€ 121 before taxes and fees
Destinations to explore
- Key West Holiday rentals
- Varadero Holiday rentals
- Naples Holiday rentals
- Miami Holiday rentals
- Miami Beach Holiday rentals
- Havana Holiday rentals
- Fort Lauderdale Holiday rentals
- Boca Raton Holiday rentals
- West Palm Beach Holiday rentals
- Sarasota Holiday rentals
- Anna Maria Island Holiday rentals
- Tampa Holiday rentals
- Family-friendly rentals United States
- Family-friendly rentals Florida
- Family-friendly rentals Key West
- Family-friendly rentals Florida Keys
- Family-friendly rentals Marco Island
- House rentals Summerland Key
- Rentals with a washing machine and dryer Summerland Key
- Rentals with a hot tub Summerland Key
- Waterfront rentals Summerland Key
- Rentals with pools Summerland Key
- Pet-friendly rentals Summerland Key
- Monthly Rentals Summerland Key
- Rentals with a kayak Summerland Key
- Family-friendly rentals Summerland Key
- Rentals with outdoor seating Summerland Key
- Rentals with beach access Summerland Key
- Rentals with a patio Summerland Key
- Family-friendly rentals Monroe County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom