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Kid-friendly holiday rentals in Summerland Key

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Top-rated family-friendly rentals in Summerland Key

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

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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!

2–9 Mar

€ 900 per night

Guest favourite

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.

12–19 Oct

€ 238 per night

Tiny home in Big Pine Key

4.8 out of 5 average rating, 89 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.

2–9 Jun

€ 131 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.

17–24 Jan

€ 402 per night

Guest favourite

Cottage in Little Torch Key

4.91 out of 5 average rating, 145 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!

25 Apr – 2 May

€ 589 per night

Guest favourite

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.

24–31 Oct

€ 203 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!

8–15 Apr

€ 478 per night

Guest favourite

Home in Cudjoe Key

4.97 out of 5 average rating, 121 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.

7–14 Oct

€ 388 per night

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 106 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.

24–31 Aug

€ 470 per night

Home in Cudjoe Key

4.81 out of 5 average rating, 220 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!

20–27 Sep

€ 450 per night

Guest favourite

Flat in Key West

4.92 out of 5 average rating, 1036 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.

28 Jul – 4 Aug

€ 309 per night

Guest favourite

Home in Cudjoe Key

4.92 out of 5 average rating, 142 reviews

Paradise at 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."

11–18 Jan

€ 443 per night

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Popular amenities for Summerland Key family-friendly rentals

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Kid-friendly house rentals

Guest favourite

Home in Marathon

4.91 out of 5 average rating, 159 reviews

Beachfront Villa - Florida Keys

20–27 Apr

€ 450 per night

Guest favourite

Home in Key Largo

4.9 out of 5 average rating, 348 reviews

Your Keys Getaway!

28 Sep – 5 Oct

€ 204 per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 117 reviews

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

22–29 May

€ 609 per night

Guest favourite

Home in Key West

4.94 out of 5 average rating, 271 reviews

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

20–27 Sep

€ 540 per night

Guest favourite

Home in Marathon

4.96 out of 5 average rating, 125 reviews

Oceanfront Tiny Villa in the Heart of the FL Keys

29 Aug – 5 Sep

€ 488 per night

Home in Cudjoe Key

4.81 out of 5 average rating, 124 reviews

Ocean View 2/2 on Canal

19–26 Aug

€ 425 per night

Guest favourite

Home in Key Colony Beach

4.96 out of 5 average rating, 134 reviews

Beautiful open plan remodeled home in Key Colony

23–30 Oct

€ 236 per night

Guest favourite

Home in Cudjoe Key

4.94 out of 5 average rating, 17 reviews

May Extravaganza - Relax in Paradise!

1–8 Oct

€ 250 per night

Family-friendly apartment rentals

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 149 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

21–28 Aug

€ 184 per night

Guest favourite

Flat in Key West

4.98 out of 5 average rating, 449 reviews

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

13–20 Apr

€ 361 per night

Guest favourite

Flat in Key West

4.94 out of 5 average rating, 359 reviews

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

14–21 Sep

€ 273 per night

Guest favourite

Flat in Key West

4.97 out of 5 average rating, 237 reviews

Poolside Truman Annex 2 Bed | Conch Life Condo

26 Mar – 2 Apr

€ 824 per night

Guest favourite

Flat in Tavernier

4.89 out of 5 average rating, 434 reviews

Capt Craigs 1 Bedroom /1 Bath Apartment

13–20 Jul

€ 213 per night

Flat in Key West

4.81 out of 5 average rating, 126 reviews

Mango Hideaway steps off World Famous Duval street

8–15 Aug

€ 351 per night

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

22–29 Oct

€ 330 per night

Guest favourite

Flat in Key West

4.91 out of 5 average rating, 703 reviews

Duval Balcony Spanky's Retreat

15–22 Dec

€ 497 per night

Family-friendly apartment rentals

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

29 Oct – 5 Nov

€ 369 per night

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

22–29 Aug

€ 253 per night

Guest favourite

Apartment in Key West

4.86 out of 5 average rating, 129 reviews

A Perfect Getaway

8–15 Dec

€ 476 per night

Guest favourite

Apartment in Marathon

4.87 out of 5 average rating, 192 reviews

Sombrero Beach Tropical Getaway

17–24 Oct

€ 263 per night

Guest favourite

Apartment in Key West

4.93 out of 5 average rating, 118 reviews

Downtown 4/4 Waterfront Penthouse Pool, Dock, Pet

22–29 May

€ 1,219 per night

Guest favourite

Apartment in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

31 May – 7 Jun

€ 241 per night

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

30 Aug – 6 Sep

€ 288 per night

Guest favourite

Apartment in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

29 Sep – 6 Oct

€ 460 per night

Quick stats about holiday 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
€ 103 before taxes and fees

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