Family-friendly holiday rentals in Summerland Key

King MSTR, SS Quartz Kitchen, Bikes Kayaks, VIEWS!

Updated waterfront 2BR/2BA with King Master, 2nd Queen and pullout couch. 35' seawall—bring your boat! Enjoy a fully stocked quartz kitchen with stainless appliances. Located in Venture Out, a quiet, family‑friendly gated resort with fishing, lobstering, pools, hot tub, pickleball, tennis, basketball, rec center, bikes, kayaks, and SUPs. Between Key West (20 mi) and Marathon. Free WiFi; Roku TVs in both bedrooms and living room. Kayaks, SUPs and storage area with extra fridge and bait freezer.

Beautiful Cottage & Amenities in Gated Community

Our comfortable, beautifully decorated two bedroom/two bathroom home with full sized kitchen is located in the Venture Out gated community. This is the perfect place if you are looking for peace in a quiet, family friendly, safe environment. Amenities include on-site convenience store, saltwater pool, spa, tennis courts, pickleball courts, a marina with marine fuel, double wide boat ramps, pool table, ping-pong, and much more, in a gated 24-hour security resort. All guests must be registered.

Beautiful Waterfront book now 2026 filling up fast

This property is like having your own private resort. We are on the Gulf of Mexico with a Million-dollar waterfront view & sunsets. 4BR + bonus room w/queen bed & futon. 2 full bathrooms 4 TVs. Pool, Private Dock. Watch the Dolphins daily. We a located next to the World-Famous Dolphin Research Center. House has wrapped around deck plenty of seating inside/out. Large private yard with plenty of room for all your needs. Walking distance to restaurant, marina. Kayaks/Paddleboards mostly available.

Blue Heaven Waterfront Home

Lobstering paradise 2 houses from open water, deep 60' canal, gorgeous water views, direct access to the Atlantic/Gulf, 35' dock/seawall. 3 zone mini split A/C and heat, overhead ceiling fans, fully stocked kitchen, microwave, washer/dryer, 42" Smart TV in living room and master bedroom, WIFI. King size bed in the master, queen bed in 2nd bedroom, and a queen sofa in the living room. Beach towels, linens. Marina store with bait & fuel onsite, 2 wide boat ramps, pool, hot tub & Rec center.

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

Discover the perfect blend of comfort, relaxation and adventure at the Sugarloaf Key Hotel, nestled within the Sugarloaf Key / Key West KOA Resort campground. Newly built in 2023, this beautiful 6-person pet-friendly vacation suite offers everything you need for a great stay. Nestled amongst gorgeous tropical scenery, this resort includes robust amenities including resort-style pool and hot tub with an adjacent pub, quaint sand beach, marina, water rentals, café, camp store and more!

Waterfront Sanctuary in the Keys!

Your WATERFRONT Keys getaway!! Updated appliances & fixtures, this 2BR/2BA elevated property won’t disappoint! Fully stocked kitchen/bathrooms. Never ending activities for your group at the Venture Out Resort- a gated community with oversized pool, hot tub, pickle ball/tennis/basketball courts, fishing, lobstering, biking, kayaking, boating! Launch your boat from the private ramp and tie it up on our 35’ seawall! Situated between Key West & Marathon, this property is THE PLACE!

Amazing houseboat with 2nd floor observation deck

Escape to our one-of-a-kind houseboat “Wild One,” anchored minutes from Soencers boat yard Key West. Surrounded by turquoise waters, enjoy one complimentary round trip per day, with times arranged around our charters. Evening rides may be available on request, last ride 10 PM. Extra charge after 8 PM Special Promotion: End your day with a private Sunset Eco Trip (6–7 PM) as your nightly ride to the houseboat—watch the sky ignite before settling in for a peaceful night afloat.

Spanish Queen @Venture Out

Experience the beautiful Florida Keys and stay at the popular Venture Out Private Community at Cudjoe Key. Newly furnished two-bedroom, 2 bath stilt home checks all the boxes for the ultimate Florida Keys Vacation. Sun- filled open floor plan allows family to spend the their precious time together cooking and entertaining. Two-2 person kayaks and 4 bikes included *** Please note that guests must pay a resort entry fee of $125 directly to security upon entry into the park***

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!

MARCH $Save $ Oceanfront 4 Bikes/2Kayaks. KING bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 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!

Waterfront Haven House with Boat Basin & Ramp!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Anchor House to reserve both homes if available). 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 point and enjoy the underwater scenery!

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.