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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.

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Cottage in Cudjoe Key

4.9 out of 5 average rating, 134 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!

Dec 13 – 20

ﺩ.ﺇ3,260 per night

Guest suite in Marathon

4.98 out of 5 average rating, 186 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.

Aug 4 – 11

ﺩ.ﺇ814 per night

Tiny home in Big Pine Key

4.8 out of 5 average rating, 92 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.

Aug 15 – 22

ﺩ.ﺇ393 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.

Aug 10 – 17

ﺩ.ﺇ1,496 per night

Home in Cudjoe Key

4.85 out of 5 average rating, 39 reviews

Relaxing Home in the Keys

This 2 bedroom, one bath home is located in Venture Out on Cudjoe Key, FL. 23 miles outside Key West!. Venture Out is a gated community that features, community pool, hot tub, tennis courts, basketball court, a private ramp, unit is 85 yards from ramp, easy for lunching kayaks. There is a dishwasher, grill, TV and free WIFI. The unit includes 2 adult bikes, 2 person Kayak and Paddle board at no extra chargeATTENTION: The community charges a non-refundable security/registration upon arrival.

Sep 20 – 27

ﺩ.ﺇ758 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 4 – 11

ﺩ.ﺇ2,027 per night

Villa in Marathon

4.89 out of 5 average rating, 148 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!

Apr 15 – 22

ﺩ.ﺇ1,652 per night

Home in Cudjoe Key

4.97 out of 5 average rating, 124 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.

Oct 14 – 21

ﺩ.ﺇ1,606 per night

Home in Marathon

4.99 out of 5 average rating, 107 reviews

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

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Sep 14 – 21

ﺩ.ﺇ1,528 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!

Aug 22 – 29

ﺩ.ﺇ1,509 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."

Apr 24 – May 1

ﺩ.ﺇ1,518 per night

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

Wow!!! Our new spacious 3 bedrooms, 2 full bath home on a 60-foot wide, deep-water canal with a 60-foot-long dock is only 1,500 feet from the open waters of Kemp Channel. Our canal enters Kemp Channel just to the north of the Overseas Highway Bridge, so that our guests bringing their boats have access to the Atlantic Ocean and the Gulf of Mexico. We have a guest friendly cancellation policy as described below in this listing.

Oct 1 – 8

ﺩ.ﺇ842 per night

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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

Mar 22 – 29

ﺩ.ﺇ1,522 per night

Home in Key West

4.97 out of 5 average rating, 206 reviews

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Aug 24 – 31

ﺩ.ﺇ1,526 per night

Home in Cudjoe Key

4.81 out of 5 average rating, 124 reviews

Ocean View 2/2 on Canal

Jul 12 – 19

ﺩ.ﺇ1,505 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

ﺩ.ﺇ1,545 per night

Home in Marathon

4.97 out of 5 average rating, 118 reviews

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

Dec 20 – 27

ﺩ.ﺇ2,469 per night

Home in Summerland Key

4.86 out of 5 average rating, 7 reviews

Bungalows at Sugarloaf Beach - Little Hammock

Dec 7 – 14

ﺩ.ﺇ1,709 per night

Home in Cudjoe Key

5.0 out of 5 average rating, 23 reviews

Paradise in Cudjoe! Perfect Family Home!

Oct 4 – 11

ﺩ.ﺇ1,450 per night

Home in Cudjoe Key

4.95 out of 5 average rating, 19 reviews

Conch Cabana in Paradise 23 miles outside Key West

Jan 13 – 20

ﺩ.ﺇ1,149 per night

Kid-friendly apartment rentals

Apartment in Key West

4.92 out of 5 average rating, 1050 reviews

At Mine | Lovely Suite steps from Duval Street

May 9 – 16

ﺩ.ﺇ904 per night

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

ﺩ.ﺇ942 per night

Apartment in Key West

4.97 out of 5 average rating, 237 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

Apr 3 – 10

ﺩ.ﺇ2,754 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 28 – May 5

ﺩ.ﺇ1,224 per night

Apartment in Key Largo

4.83 out of 5 average rating, 239 reviews

Key's Cottage Escape

Mar 17 – 24

ﺩ.ﺇ633 per night

Apartment in Key West

4.8 out of 5 average rating, 127 reviews

Mango Hideaway steps off World Famous Duval street

Nov 26 – Dec 3

ﺩ.ﺇ1,941 per night

Apartment in Tavernier

4.95 out of 5 average rating, 149 reviews

Boho FL Keys Condo

Oct 10 – 17

ﺩ.ﺇ1,102 per night

Apartment in Tavernier

4.89 out of 5 average rating, 436 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

Jul 14 – 21

ﺩ.ﺇ766 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

Oct 27 – Nov 3

ﺩ.ﺇ871 per night

Condo in Key Colony Beach

4.96 out of 5 average rating, 171 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Nov 18 – 25

ﺩ.ﺇ1,376 per night

Condo in Key West

4.86 out of 5 average rating, 130 reviews

A Perfect Getaway

Jul 20 – 27

ﺩ.ﺇ1,593 per night

Condo in Key West

4.89 out of 5 average rating, 148 reviews

Large waterfront 2/2 end unit with boat slip

Mar 22 – 29

ﺩ.ﺇ2,670 per night

Condo in Marathon

4.87 out of 5 average rating, 192 reviews

Sombrero Beach Tropical Getaway

Nov 10 – 17

ﺩ.ﺇ852 per night

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Sep 21 – 28

ﺩ.ﺇ982 per night

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Apr 1 – 8

ﺩ.ﺇ2,036 per night

Condo in Tavernier

4.99 out of 5 average rating, 102 reviews

Ocean View Corner Penthouse | Ocean Pointe 5416

Sep 7 – 14

ﺩ.ﺇ1,337 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
ﺩ.ﺇ404 before taxes and fees

Destinations to explore