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Cottage vacation rentals in Big Pine Key

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Top-rated cottage rentals in Big Pine Key

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An American flag is displayed on a balcony, gently waving in the ocean breeze. The calm waters are reflected under a cloudy blue sky, creating a serene atmosphere. White railings and chairs frame the view, emphasizing the oceanfront location.

Cottage in Cudjoe Key

4.9 out of 5 average rating, 158 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!

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

4.93 out of 5 average rating, 135 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

Updated, waterfront, 2BR, 2BA with King Master and a 35' seawall.Bring your boat!Fully stocked kitchen w stainless appliances. So much to do here for up to 6 at this family-friendly, quiet resort-Venture Out, a gated,secure community. Fishing, lobstering, oversized pool, children's pool, hot tub, pickleball, tennis and basketball courts.Rec center. Bike, kayak, and SUPs.Between Key West(20Mi)and Marathon, this property and area is not to be missed! Free WIFI; Both bedrooms and LR have Roku TVs.

An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.

Cottage in Cudjoe Key

4.87 out of 5 average rating, 69 reviews

Turtle Cove 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. ** TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of

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.

Cottage in Cudjoe Key

4.72 out of 5 average rating, 156 reviews

Calypso Cottage

This reimagined vintage style waterfront home is everything! With the ability to tie up to 17f boat (larger boat? just ask!) right outside your door, enjoy the many amenities of the home (kayaks, bikes, beach & snorkel gear, board games, wifi & roku) and of the community (Pools, spa, boat launch, pickle ball, bocce, tennis) even a library and general store!). This is a magical location to launch all your Florida keys adventures! Canal patio for drinks? Lush screen porch for coffee? It's on!

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.

Cottage in Cudjoe Key

4.9 out of 5 average rating, 31 reviews

Conch Cabana in Paradise 23 miles outside Key West

Sparkling clean and bright 2Bd/2Ba vacation home in Venture Out Resort! Is located on a 60' wide canal, our Dock is 35’. With fish clean table, cleats, bumpers, shower and patio table with 4 chairs. 1 porch front yard and 1 Deck over looking the water. Just a few steps from the pool, hot tub , please be aware that they can close the pool and hot tub for emergency/ regular maintenance without any notice. VO Resort has a marina w/fuel, store, rec hall, tennis court. Great Restaurant nearby !

Cottage in Key West

5 out of 5 average rating, 4 reviews

Key West Cottage Du Soleil w/ Pool!

This two-bedroom Key West Writer's Cottage is a serene haven for creative minds and vacationers. It features a cozy living area with charming decor that inspires relaxation. Enjoy the relaxing deck for morning coffee or unwinding with a book, and take a refreshing dip in the inviting pool. Each comfortably furnished bedroom ensures a restful night’s sleep, and the fully equipped kitchen is perfect for cooking. Plus, you can easily bike to the nearby boardwalk and beach for fun in the sun!

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

Cottage in Little Torch Key

4.88 out of 5 average rating, 171 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!

The private saltwater pool is framed by tropical plants and bright blue sky. Lounge chairs are positioned nearby, alongside decorative elements and pots. The serene atmosphere offers a refreshing retreat, inviting relaxation and enjoyment in the beautiful surroundings.

Cottage in Key Colony Beach

5 out of 5 average rating, 12 reviews

Luxurious Oasis on: 2BR w/Private Pool, Tiki, Dock

Lilo's in The Keys, a tropical paradise! This cherished waterfront gem has been a beloved destination for years. The perfect getaway to unwind and indulge in the island lifestyle. Nestled among tropical landscaping, Lilo’s boasts a private saltwater pool, a tiki patio for outdoor lounging and a dock for your boat. Your stay includes kayaks, so you can explore the beauty of Key Colony Beach at your own pace. The home is fully equipped with all the comforts of home.

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.

Cottage in Cudjoe Key

4.62 out of 5 average rating, 118 reviews

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

This mid-rise home is fully furnished with high ceilings throughout! The living room offers a flat screen television with sleeper sofa. Master bedroom features a queen bed with full bathroom and flat screen television. Guest bedroom features a full size bed and half bath. Additional amenities include large open porch with table and chairs, gas grill and central air conditioning and heat. Free WiFi offered in unit and in Community Recreation Center.

A charming yellow cottage is framed by a white picket fence, with blue awnings above the windows and door. The entrance is marked by a simple white door. Lush greenery surrounds the property, enhancing the inviting appearance of the home.

Cottage in Key West

4.91 out of 5 average rating, 141 reviews

The Dancing Rooster - 1 Block to Duval!

Located just 2 short blocks from Duval and in the center of downtown, the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house. The Southernmost Retreat is part of the Simonton Historic Cottage enclave and is surrounded by fine restaurants, art galleries, shopping and proximate to all attractions in the Old Town District. No car is needed as you can walk to the beaches and all of the famous attractions.

A sailboat is moored near a wooden dock, surrounded by palm trees. The orange glow of sunset is visible in the background, reflecting on the calm water. The scene captures a tranquil moment along the bay.

Cottage in Marathon

4.96 out of 5 average rating, 26 reviews

Waterfront cottage w/ MotherInLaw suite&boat slip

The property is on the Bay, with a balcony in the palm trees and a large back porch on the water. Includes a ComPac sailboat, use of kayaks, bicycles and BBQ grill. Boat slip included! Located at Mile Marker 63, on Conch Key, the location is convenient to all Keys attractions: Key West, MM zero, State Parks, Museums, shopping, snorkeling and diving, and some of the best fishing in the world.

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.

Cottage in Marathon

4.82 out of 5 average rating, 39 reviews

Prime Location 1B/1B Home

Welcome to your perfect Florida Keys getaway! This delightful, coastal-themed 1-bedroom, 1-bathroom cottage is your temporary escape pod, nestled within the Sun Outdoors Marathon RV Resort. We're perfectly situated for exploring the best of the Keys, local beaches (where your biggest decision is 'flip-flops or bare feet?', stunning reefs (hello, Nemo!), and fantastic restaurants.

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Popular amenities for Big Pine Key cottage rentals

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.

Cottage in Cudjoe Key

4.81 out of 5 average rating, 100 reviews

OCEANIA... water front cottage retreat ~

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.

Cottage in Cudjoe Key

4.88 out of 5 average rating, 40 reviews

Tidewater Views at Venture Out

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.

Cottage in Cudjoe Key

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.

Cottage in Cudjoe Key

4.78 out of 5 average rating, 64 reviews

NAUTILUS...ocean front cottage retreat ~

A bright living area features a comfortable gray sofa and an upholstered ottoman. Large sliding doors open to a water view, letting in natural light. A small dining table with patterned chairs is positioned near the window, complemented by a ceiling fan and modern decor.

Cottage in Key Colony Beach

4.55 out of 5 average rating, 11 reviews

2BR dog-friendly water view stay, resort amenities

Pet-friendly cottage rentals

The exterior view features a charming cottage framed by lush greenery and tropical plants. French doors open onto a wooden deck, inviting guests into the living space. A stone pathway leads to the entrance, while seating is offered nearby under the natural shade of palm trees.

Cottage in Key West

4.8 out of 5 average rating, 20 reviews

Colony Sunset- Bright and airy cottage

A charming outdoor space is shown with a small circular table and two chairs set on a stone patio. Lush greenery surrounds the area, and wooden steps lead to the entrance of the cottage. A tree provides shade, enhancing the serene ambiance.

Cottage in Key West

4.84 out of 5 average rating, 86 reviews

Hidden Oasis @ the Colony ~ Great location

Cottage in Marathon

4.62 out of 5 average rating, 13 reviews

Waterview 1B/1B Tiny Home

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.

Cottage in Marathon

4.71 out of 5 average rating, 7 reviews

Waterfront 1B/1B Tiny Home

A charming exterior of a light blue house is shown against a clear sky. The house features large front windows, a decorative round window, and a small front porch with steps leading up. Outdoor seating in turquoise is visible nearby, set on a gravel driveway.

Cottage in Marathon

4.69 out of 5 average rating, 42 reviews

Cute 1B/1B Lofted Cottage

Top guest favorite

A charming outdoor patio area features a circular table with two chairs set on stone pavers surrounded by lush tropical plants. A canopy of palm trees provides shade, while the bright yellow exterior of the cottage is visible in the background.

Cottage in Key West

4.9 out of 5 average rating, 10 reviews

NEW! - The Jolly Rooster Cottage - Walk to Duval

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.

Cottage in Marathon

4.43 out of 5 average rating, 222 reviews

Tropical Cottages - Cottage # 03

A charming yellow cottage is visible, featuring a white door and a small window above it. Two blue chairs are positioned in front, surrounded by lush greenery and palm trees. The pathway is made of brick, enhancing the inviting exterior of the cottage.

Cottage in Marathon

4.63 out of 5 average rating, 251 reviews

Tropical Cottages - Cottage # 8

Private cottage rentals

An outdoor dining area is situated on a covered porch overlooking expansive water views. A large table is set with colorful dishware in blue and turquoise. Yellow kayaks are visible on the dock, complementing the serene backdrop of the water and sky.

Cottage in Cudjoe Key

4.87 out of 5 average rating, 69 reviews

Turtle Cove Views at Venture Out

A waterfront property is surrounded by lush palm trees, with a gravel area leading to a private dock. The home is painted in soft blue tones, reflecting a comfortable coastal vibe. The expansive water views offer shimmering reflections under the clear sky.

Cottage in Little Torch Key

4.88 out of 5 average rating, 171 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

A coastal view features multiple white houses with balconies situated along the waterfront. Palm trees sway gently in the breeze, and clear blue skies create a serene backdrop. Vehicles are parked in the driveways, emphasizing accessibility to the beachfront.

Cottage in Cudjoe Key

4.9 out of 5 average rating, 10 reviews

Ocean Breeze at Venture Out 537

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

4.93 out of 5 average rating, 135 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

A private deck area features two gray chairs and a small glass table, surrounded by lush tropical foliage. The deck offers an inviting exterior view of the cottage, with a white lattice screen providing added privacy.

Cottage in Key West

4.63 out of 5 average rating, 16 reviews

Colony Calypso - A quaint 1 Bedroom Cottage

Top guest favorite

A charming outdoor patio area features a circular table with two chairs set on stone pavers surrounded by lush tropical plants. A canopy of palm trees provides shade, while the bright yellow exterior of the cottage is visible in the background.

Cottage in Key West

4.9 out of 5 average rating, 10 reviews

NEW! - The Jolly Rooster Cottage - Walk to Duval

Cottage in Key West

5 out of 5 average rating, 4 reviews

Key West Cottage Du Soleil w/ Pool!

A living room features soothing blue and green tones, complemented by a vibrant green accent chair and decorative pillows. French doors open to the lush courtyard, allowing natural light to enhance the space, while a decorative rug and a glass coffee table provide a cozy gathering area.

Cottage in Key West

4.86 out of 5 average rating, 50 reviews

Namaste: A blissful one bedroom cottage

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