Vacation rentals with a kayak in Sugarloaf Key

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Top-rated kayak rentals in Sugarloaf Key

Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A serene waterfront view showcases clear turquoise waters under a bright blue sky. A boat can be seen cruising along the horizon, while a patio with seating is visible at the forefront, adjacent to a dock lined with black posts.

Cottage in Cudjoe Key

4.94 out of 5 average rating, 181 reviews

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.

ValueOutdoor spacesGetting around

Guest favorite

A serene view of a waterfront canal is captured from a covered porch. The calm water reflects the sky, with boats docked along the edges. Palm trees gently sway in the breeze, enhancing the coastal setting. Nearby structures suggest a vibrant community atmosphere.

Home in Cudjoe Key

4.81 out of 5 average rating, 324 reviews

SEPT/OCT. Save$Oceanfront 4 BIKE/2 Kayak KING Bed

*PERFECT LOCATION! * 35' Seawall *AWESOME 2 bedroom 2 full bath waterfront stilted house in Cudjoe Key. At MM# 23 only 25min to Key West. In a gated community of Venture Out Resort. *Sleeps 6 *55" TV *A/C *Fully equipped kitchen *Includes grill, 4 Bikes & 2 two-person Kayaks *PLUS: Pool, HotTub, Marina, Boat Ramp, Store, Playground, Game Room, Tennis, Library. Too much to list! WE WILL NEED YOUR EMAIL WHEN YOU CONFIRM THE BOOKING IN ORDER TO SEND YOU THE REGISTRATION FORMS AND THE RULE PACKET.

Outdoor spacesLocationParking

Top guest favorite

Home in Cudjoe Key

5.0 out of 5 average rating, 51 reviews

Oceanfront Cottage with Open Water Views

Oceanview Serenity provides stunning open water views, and a 60 foot seawall for your boat. Comes with paddle board, kayaks, and more. Newly renovated 2BR cottage sleeps MAXIMUM OF FOUR (4) GUESTS, with a King in the Master BR and one Queen size bed Guest BR (both with new JW Marriott mattresses for comfort). All new appliances! Enjoy resort amenities like a pool, hot tub, tennis, and marina store. Just 30 minutes from Key West. One-time $125 RESORT FEE DUE AT CHECK-IN (PER STAY, NOT PER PERSON

LocationOutdoor spacesComfort

Superhost

Home in Cudjoe Key

4.92 out of 5 average rating, 98 reviews

Oceanfront w/ Dock, Swimming pool, Hot Tub, Kayaks

Your Luxury Keys Getaway! Experience stunning Ocean views, amazing sunsets and sunrises, a 35' canal-front seawall, kayaks, bikes, outdoor shower, fish cleaning station & bait freezer. Everything you need to fully enjoy the Keys experience! Keep your boat at the house and be on the Atlantic or Gulf in minutes. Located halfway between Key West and Marathon, you get access to all resort amenities: heated pool, hot tub, pickleball courts, boat launch & store. Prime dates go fast, book now!

ValueLocationDecor

Superhost

An aerial view captures a vibrant community of stilt homes nestled along the coastline, with clear blue waters stretching in the background. Lush palm trees dot the landscape, while a distinctive red marker indicates a specific location within this scenic setting.

Home in Cudjoe Key

4.84 out of 5 average rating, 130 reviews

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 a resort entry fee of $125 is charged per Whole group per stay directly to security upon entry into the park***

LocationOutdoor spacesBeach

Superhost

A bright living area features light-colored furnishings with nautical accents. Large windows offer views of the water, while a flat-screen TV is positioned on a stylish stand. The adjoining dining area showcases a white table with matching chairs surrounded by plants, enhancing the airy environment.

Cottage in Cudjoe Key

4.79 out of 5 average rating, 121 reviews

OCEANIA... water front cottage retreat ~

OCEANIA... water front cottage retreat ~ Completely remodeled, direct cannal-front cottage offers everything you'll need for the perfect getaway. Boat dock (35ft), HD Smart TVs, washer & dryer, S/S appliances! 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!

LocationValueAmenities

Guest favorite

The image showcases a vibrant living space within the Dapper Dolphin condo, featuring a stylish kitchen with granite countertops, a cozy dining area, and a comfortable bedroom with a king-sized bed. The outdoor area displays a large pool surrounded by lounge chairs, highlighting the resort's inviting atmosphere.

Condo in Marathon

4.93 out of 5 average rating, 119 reviews

Dapper Dolphin | Canal View + Breakfast + Pool

Escape to The Dapper Dolphin, a beautifully updated coastal 1-bedroom, 1-bath condo located at Skipjack Resort & Marina in the heart of Marathon. Sleeping up to 4 guests, this stylish retreat features a full kitchen, private balcony, and resort amenities including a pool, Tiki Bar, restaurant, Marina, and more. Situated in the heart of Marathon, it offers proximity to the beach, restaurants, activities, and all the essentials for an unforgettable vacation experience right on-site!

LocationOutdoor spacesDecor

Guest favorite

The living area features a spacious sectional sofa facing a large window with multiple shutters, allowing natural light to fill the room. A modern coffee table is situated on a soft area rug, complemented by dining stools near the open kitchen with updated appliances.

Home in Cudjoe Key

4.88 out of 5 average rating, 161 reviews

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!

LocationOutdoor spacesCheck-in

Superhost

An aerial view showcases a private beach with clear blue waters and a sandy shore. A wooden dock extends into the water, while lush palm trees frame the scene. A bungalow with a unique octagonal deck is positioned near the beach, offering scenic views.

Home in Sugarloaf Key

4.81 out of 5 average rating, 175 reviews

Mi Azucar

POOL WILL BE CLOSED FOR MAINTENANCE FROM 8/28/2026 - 9/19/2026 / PERFECT TIME TO TAKE ADVANTAGE OF OUR 50% OFF OUR NIGHTLY RATE Wake up to breathtaking sunrises from the master bedroom, complete with direct access to a private deck overlooking the water. The second floor boasts an open-concept family area, where panoramic ocean views surround you. French doors lead to a second deck, offering a tranquil setting to take in the beauty of the ocean and the natural surroundings.

LocationOutdoor spacesAccess

Top guest favorite

Home in Cudjoe Key

4.97 out of 5 average rating, 60 reviews

Tiki Time in Cudjoe Key 136

Open water, upscale Oceanfront Retreat! This waterfront gem offers amazing views of the Atlantic Ocean and is the perfect getaway for your next vacation in Paradise. This 2 bedroom, 2 bathroom vacation home is equipped with everything you need to unwind and relax. Offering a high end kitchen, stainless appliances, three smart tv's and a 54-foot seawall to dock your boat. VO COMMUNITY REGISTRATION FEE OF $125.00 IS DUE UPON ARRIVAL IN CASH OR CREDIT CARD ONLY.

LocationValueBiking

Superhost

A comfortable outdoor seating area is showcased, with bright blue cushions arranged around a dark table. The view overlooks crystal-clear waters, and decorative lanterns provide soft lighting. A potted flower adds a touch of color beside the seating, enhancing the peaceful ambiance by the water.

Home in Cudjoe Key

4.88 out of 5 average rating, 136 reviews

*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.

ValueLocationBeach

Superhost

A well-lit sleeping area features a spacious bed with decorative pillows and a cozy throw. Light wood accents and modern furnishings complement the room. A kitchenette area includes a mini fridge and Keurig coffee maker, with curtains providing separation and natural light from the windows.

Tiny home in Summerland Key

4.82 out of 5 average rating, 94 reviews

Bungalow

Pet-friendly glamping in The Keys. Camp in comfort on your next Key West escape in an air-conditioned bungalow. Close to our amenities. Featuring a living room (with sleeper sofa), bathroom with shower, and a king-size bed, this vacation rental getaway sleeps 4. Our bungalows also boast patio table seating for four, Smart streaming TV, Wi-Fi, microwave, mini fridge, Keurig coffee maker, blow dryers, charcoal grill, and steamers.

Outdoor spacesLocationKitchen