We’re sorry, some parts of the Airbnb website don’t work properly without JavaScript enabled.

Airbnb your place

Kid-friendly vacation rentals in Summerland Key

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Summerland Key

Guests agree: these kid-friendly rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

1 of 3 pages

Cottage in Cudjoe Key

4.91 out of 5 average rating, 133 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!

Mar 5 – 12

R16,686 ZAR per night

Home in Cudjoe Key

4.81 out of 5 average rating, 124 reviews

Ocean View 2/2 on Canal

Hurricane Ian did no damage This is a non-smoking, no pets, canal front home with a 35' sea wall. Ocean views from either deck. Vaulted great room. Fully equipped kitchen and linens with two private bed/bath suites offering privacy. The resort is gated and secure with plenty of amenities: a small tiki beach, marina, large pool, hot tub, pickle ball, tennis,laundry and general store. One time $113.00 resort fee Required to book: 1. verified identity 2. have positive reviews on AIrbnb

Jul 27 – Aug 3

R7,701 ZAR per night

Guest suite in Marathon

4.98 out of 5 average rating, 185 reviews

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Oct 12 – 19

R4,168 ZAR per night

Home in Cudjoe Key

4.9 out of 5 average rating, 104 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

Jun 23 – 30

R7,657 ZAR per night

Cottage in Little Torch Key

4.91 out of 5 average rating, 146 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Feb 13 – 20

R10,376 ZAR per night

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Nov 5 – 12

R3,588 ZAR per night

Villa in Marathon

4.89 out of 5 average rating, 145 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Mar 13 – 20

R8,453 ZAR per night

Home in Cudjoe Key

4.97 out of 5 average rating, 122 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

Aug 30 – Sep 6

R7,073 ZAR per night

Home in Cudjoe Key

4.81 out of 5 average rating, 221 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. Located in the lower Florida Keys at MM# 23 only 25minutes to Key West. Located in the gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C & heat *Fully equipped kitchen *Brand New Amenities including grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library, etc. Too much to list!

Sep 14 – 21

R7,721 ZAR per night

Apartment in Key West

4.92 out of 5 average rating, 1045 reviews

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Jul 28 – Aug 4

R5,446 ZAR per night

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise and Cudjoe Bay

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

Jan 17 – 24

R7,767 ZAR per night

Camper/RV in Big Pine Key

4.93 out of 5 average rating, 41 reviews

Having fun in the lower Keys

Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

May 9 – 16

R2,319 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Summerland Key kid-friendly rentals

Free parking on premises

Air conditioning

Kid-friendly house rentals

Home in Marathon

4.91 out of 5 average rating, 159 reviews

Beachfront Villa - Florida Keys

Nov 11 – 18

R7,787 ZAR per night

Home in Marathon

4.99 out of 5 average rating, 107 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

Aug 24 – 31

R6,947 ZAR per night

Home in Marathon

4.96 out of 5 average rating, 125 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

Aug 11 – 18

R8,158 ZAR per night

Home in Key Largo

4.9 out of 5 average rating, 349 reviews

Your Keys Getaway!

Mar 11 – 18

R3,567 ZAR per night

Home in Marathon

4.97 out of 5 average rating, 118 reviews

Marathon one-level home on the Marina - with slip!

Dec 3 – 10

R12,279 ZAR per night

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

Oct 1 – 8

R4,310 ZAR per night

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

Oct 4 – 11

R7,415 ZAR per night

Home in Summerland Key

4.86 out of 5 average rating, 7 reviews

Bungalows at Sugarloaf Beach - Little Hammock

Feb 23 – Mar 2

R9,497 ZAR per night

Kid-friendly apartment rentals

Apartment in Key West

4.94 out of 5 average rating, 360 reviews

Studio Blu - Key West, FL - Hip Studio in Old Town

Sep 14 – 21

R4,803 ZAR per night

Apartment in Key West

4.98 out of 5 average rating, 450 reviews

Bella Vita: 1B/1B Condo for 2 Just Steps off Duval

Apr 26 – May 3

R6,389 ZAR per night

Apartment in Key West

4.9 out of 5 average rating, 212 reviews

Starr's Suite - 2 person K Suite w/Private Spa!

Jan 4 – 11

R10,968 ZAR per night

Apartment in Tavernier

4.95 out of 5 average rating, 149 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

Aug 24 – 31

R3,498 ZAR per night

Apartment in Key West

4.8 out of 5 average rating, 127 reviews

Mango Hideaway steps off World Famous Duval street

Aug 8 – 15

R6,259 ZAR per night

Apartment in Key West

4.91 out of 5 average rating, 705 reviews

Duval Balcony Spanky's Retreat

Sep 14 – 21

R9,425 ZAR per night

Apartment in Key West

4.84 out of 5 average rating, 213 reviews

The Bartlum | Luxury Studio In Prime Location!

Jun 11 – 18

R9,521 ZAR per night

Apartment in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

Apr 20 – 27

R7,915 ZAR per night

Kid-friendly condo rentals

Condo in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Aug 22 – 29

R4,459 ZAR per night

Condo in Key Colony Beach

4.97 out of 5 average rating, 196 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

Oct 4 – 11

R5,393 ZAR per night

Condo in Key West

4.86 out of 5 average rating, 129 reviews

A Perfect Getaway

Jan 3 – 10

R9,723 ZAR per night

Condo in Marathon

4.87 out of 5 average rating, 192 reviews

Sombrero Beach Tropical Getaway

Dec 31 – Jan 7

R4,466 ZAR per night

Condo in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

Dec 23 – 30

R20,491 ZAR per night

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Jul 4 – 11

R4,909 ZAR per night

Condo in Key Largo

4.98 out of 5 average rating, 115 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Nov 7 – 14

R9,359 ZAR per night

Condo in Tavernier

4.93 out of 5 average rating, 134 reviews

It's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba

Nov 11 – 18

R5,148 ZAR per night

Quick stats about vacation rentals that are kid-friendly in Summerland Key

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with a pool
20 properties have a pool
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
930 reviews
Nightly prices starting at
R2,067 ZAR before taxes and fees

Destinations to explore