Cottage vacation rentals in Marathon

An aerial view of the property showcases a spacious swimming pool surrounded by lounge chairs. Lush greenery frames the area, enhancing the private setting. A nearby cottage is visible, along with a shaded patio area for outdoor relaxation.

4.97 out of 5 average rating, 97 reviews

Islamorada bungalow 2 bed & pool

Welcome to paradise! Completely remodeled and immaculately maintained, Bungalow Blue is nestled away in the quiet quaint Shady Palms community of 7 cottages in Islamorada, MM 76. Ideally situated next to the community heated pool, down the street from private boat ramp. If you're looking to relax and unwind while also being close to all that Islamorada has to offer, this is the place for you. Enjoy the FL Keys lifestyle in your private backyard, take a bike ride to World Famous Robbie's Marina

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.

4.94 out of 5 average rating, 156 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.

A wide view of the community pool area showcases the saltwater pool surrounded by lounge chairs and tables. The water glistens under a clear blue sky, with palm trees gently swaying in the breeze. Nearby homes are visible, creating a serene atmosphere.

4.96 out of 5 average rating, 100 reviews

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.

Two bright blue Adirondack chairs and a small table are positioned on a wooden dock overlooking calm water. Lush greenery frames the scene, while a clear blue sky enhances the tranquil atmosphere. The dock offers direct access to the water, inviting relaxation.

4.96 out of 5 average rating, 57 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage with Dockage. Short walk to world famous Lorelei for sunset celebrations. Great location for kayaking & paddleboarding. Custom length of stays can be arranged if booking a sandbar/fishing charter with our family. The fishing cottage built in the 1940s is not fancy, as photos show, but in the heart of Islamorada! Dockage available for additional $25 per night fee not included in nightly rate. Free trailer storage on site. Pet friendly :) 1 pet under 20 lb $150 fee.

5 out of 5 average rating, 93 reviews

My Little Paradise

Your slice of paradise. Brand new Cottage with all new appliances, bed, Sofa and TV's. This is a waterfront property located at Manatee Cove. Kayak and flotation devices included for you to use during your stay. Use our kayak at your own risk. By far the best place for Kayaking, Fishing and relaxing by the pool area or grill your catch of the day on the outdoor BBQ. Free internet, Tesla charging station is available and included with your rental. NO BOATS OR JET SKIS ALLOWED ON THIS PROPERTY.

4.94 out of 5 average rating, 95 reviews

2 bedroom & 25' Boat Dock Waterfront Atlantic Side

ACTUAL LOCATION: within KeyLargoKampground.com Gated Community Lot #66 with BOAT DOCK for 25' OUTSIDE: ~ Large deck/ dock, Grill, Swim Ladder, tiki hut with swing and dining and Pub table. Parking for 1 truck & 1 car. ~ steps from the cottage Dock out back in 30' deep 100' wide Deep water swim canal with tropical fish along the banks, occasional Manatee, tarpon and finger mullet in cooler months. Maybe a porpoise. Kayack, board or Fish off dock. Walk to moon lit beaches in the park.

An outdoor seating area features a round table surrounded by iron chairs, overlooking tranquil waters. Lounge chairs are positioned along the railing. The covered porch provides shade, with lush greenery visible across the waterway, enhancing the serene setting.

4.89 out of 5 average rating, 44 reviews

Tidewater Views at Venture Out

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! ** Last Key Realty requires a credit card on file for all reservations. ** TIDEWATER VIEWS is a cozy 800 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out Resort: a heated 80-foot pool with large Jacuzzi and Kiddie Pool,

A shaded seating area under thatched roofing features comfortable, woven furniture arranged around a wooden table. The serene waterway is visible beyond, with palm trees framing the view. Soft lighting creates a cozy ambiance for relaxation at sunset.

4.96 out of 5 average rating, 181 reviews

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

Cottage in Little Torch Key

4.89 out of 5 average rating, 176 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!

A serene pool area is surrounded by lush tropical plants and swaying palm trees under a clear blue sky. A large blue umbrella provides shade over a lounging area, enhancing the inviting atmosphere of the outdoor space.

4.97 out of 5 average rating, 131 reviews

2br/1ba w heated pool, 1 mile to robbies marina

Your slice of Islamorada awaits at the Key Lime Cottage! Step inside this charming 2 bedroom cottage and you will instantly feel at home. Located in the heart of the Florida Keys yet nestled in a serene neighborhood, it offers the perfect blend of comfort and relaxation. With a full kitchen, access to a gorgeous pool shared with only 6 other homes, outside seating with grill and a fire pit, beach chairs and key lime treats - there is something for everyone!

An aerial view of the pool area reveals a large, rectangular swimming pool surrounded by lounge chairs and palm trees. The layout includes shaded cabanas, and the nearby landscape features a sandy area leading to the water's edge.

4.92 out of 5 average rating, 91 reviews

Spacious cottage - the Calusa campground-keylargo

Comfortable and spacious cottage in the center of KEY LARGO, close to all activities, Publix, bars and restaurants. ENJOY THE BEST SUNSETS OF THE FLORIDA KEYS IN THE HAMMOCK AREA. The facility park has a heated pool, basketball court, tennis court, boat ramp, marina and a children’s playground. Calusa is conveniently located next to John Pennekamp Park, Fishing Charters, Snorkeling, Scuba Diving and some of the best Seafood restaurants in town.

A window reveals a lush garden filled with tropical plants and flowers. The words 'Keys Life' are displayed on a wooden sign above the window, enhancing the connection to the surrounding nature.

4.9 out of 5 average rating, 390 reviews

Cottage By The Sea

Cottage By The Sea....Your home away from home in the Florida Keys!!! Our 2 bedroom Guest House is located on the Oceanside of Key Largo in a quaint and quiet neighborhood, with a huge yard surrounded by exotic flowers and trees. Be sure to meet Frank out 120 pound Sulcata tortoise.Minutes from either Oceanside or Bayside boat ramps. It is walking distance to a famous local's Tiki Bar and Restaurant as well as Jet ski and Kayak rentals

Popular amenities for Marathon cottage rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

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.

4.82 out of 5 average rating, 105 reviews

OCEANIA... water front cottage retreat ~

The exterior of a mid-rise home is shown, featuring a light-colored facade and a set of stairs leading to an elevated porch. The porch area is equipped with a table and umbrella, surrounded by tropical landscaping and a gravel driveway.

4.63 out of 5 average rating, 123 reviews

VO Community 501 Midrise 2Bd/1.5Ba Large Open Deck

A bright window offers views of the canal and vibrant outdoor scenery. Two stools are positioned in front of the window, inviting guests to relax and enjoy the surroundings. Colorful decorations add a charming touch to the space, enhancing the coastal atmosphere.

4.69 out of 5 average rating, 170 reviews

Calypso Cottage

The exterior of the Conch Cottage features a light green facade with large windows allowing natural light. Palm trees frame the entrance, and a clear driveway leads to the door marked with the number 315. A window air conditioning unit is also visible.

3.5 out of 5 average rating, 4 reviews

Cozy, Perfect Conch Cottage! - VO315

An aerial view presents a light blue cottage alongside a canal, with white lounge chairs positioned on the deck. A kayak rests in the water, surrounded by lush palm trees and calm, clear waters reflecting a bright blue sky.

4.79 out of 5 average rating, 67 reviews

NAUTILUS...ocean front cottage retreat ~

Cottage in Key Colony Beach

4.5 out of 5 average rating, 12 reviews

2BR dog-friendly water view stay, resort amenities

An aerial view captures the vibrant community of Venture Out Residential Condominium, showcasing homes along the canal. Boats are docked nearby, and palm trees surround the outdoor seating areas. The clear water reflects the buildings, creating a serene waterfront atmosphere.

4.91 out of 5 average rating, 33 reviews

Conch Cabana in Paradise 23 miles outside Key West

Pet-friendly cottage rentals

A charming blue exterior of the rental is complemented by a wooden deck, creating an inviting entrance. Lush palm trees and surrounding greenery enhance the outdoor space, while large windows provide ample natural light to the interior.

4.8 out of 5 average rating, 30 reviews

Keys Cottage with Sleeping Loft Sleeps 6

The cottage interior features a spacious sleeping area with a king-size bed dressed in a patterned cover. Light flows in through windows, complemented by a rattan chair and a small lamp. Bunk beds are visible in a semi-separate area, with artistic decor adding a whimsical touch.

4.77 out of 5 average rating, 13 reviews

Cottage w/ Private Yard, Free Kayaks, Boats, Etc

A covered outdoor seating area features a round glass table and two chairs overlooking the blue ocean, framed by vibrant green palm trees. The tranquil beachfront path can be seen in the distance, promoting an inviting atmosphere for relaxation.

4.63 out of 5 average rating, 16 reviews

Waterfront Keys Cottage w/ Sleeping Loft Sleeps 7

An outdoor seating area is highlighted by a round wooden table surrounded by Adirondack chairs. A ceiling fan adds comfort, and the scene features expansive views of the water, with a dock visible in the background under a clear blue sky.

4.63 out of 5 average rating, 8 reviews

Waterfront Keys Cottage w/ Sleeping Loft Sleeps 8

4.69 out of 5 average rating, 45 reviews

1 Bdrm Keys Cottage with Sleeping Loft Sleeps 7

A charming cottage exterior features light blue siding and is accented by vibrant pink Adirondack chairs. Lush greenery surrounds the entrance, and flowering plants add color to the setting. A clear blue sky and tropical palm trees complete the welcoming atmosphere.

4.58 out of 5 average rating, 146 reviews

Tropical Cottages - Cottage # 10

A charming green cottage is surrounded by a landscaped area featuring palm trees. A wooden deck leads to the front entrance, and bright blue chairs are positioned on the gravel patio. A neighboring structure is partially visible in the background.

4.83 out of 5 average rating, 47 reviews

1 Bdrm Keys Cottage With Sleeping Loft Sleeps 7

The spacious cottage interior showcases two queen size beds with light bedding, set against soft blue walls. A ceiling fan adds to the airiness, while a small dining table with black chairs sits nearby. A kitchenette area is visible in the background.

4.45 out of 5 average rating, 231 reviews

Tropical Cottages - Cottage # 03

Private cottage rentals

4.9 out of 5 average rating, 119 reviews

Waterfront Getaway | Kayaks, Private Dock & BBQ

A modern house with large windows allows natural light to fill the space. The exterior features a light grey finish with white trim and a welcoming porch. Lush tropical landscaping, including palm trees and vibrant greenery, surrounds the property, creating a serene and inviting entrance.

5 out of 5 average rating, 48 reviews

Kampground Paradise w/Kayaks, Heated Pool & Marina

Cottage in Key Colony Beach

5 out of 5 average rating, 12 reviews

Keys Waterfront Oasis • Tiki • Private Pool • Dock

An open living area features wooden beam ceilings and large windows that allow natural light to fill the space. A cozy seating nook includes a table with built-in storage, while a view of an outdoor seating area can be seen through glass doors.

4.78 out of 5 average rating, 165 reviews

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

4.92 out of 5 average rating, 93 reviews

Kampground Escape /w Kayaks, Heated Pool And More

4.79 out of 5 average rating, 84 reviews

Serene Cozy Cottage in Islamorada with Heated Pool

4.86 out of 5 average rating, 50 reviews

Welcome to the Islands- Pool-Marina-Kayak

A serene outdoor seating area features a round white table and two blue chairs, positioned on a deck overlooking calm waters. Lush greenery and distant homes can be seen along the shoreline, reflecting the tranquility of the Florida Keys.