Beachfront vacation rentals in Big Pine Key

Tiny homes in Big Pine Key

A well-maintained 28-ft Grey Wolf RV is parked on a gravel lot, surrounded by tropical greenery. Two lounge chairs are positioned on a green patch of grass, creating a relaxing outdoor seating area. Sunshine filters through the clouds, adding a bright ambiance to the scene.

4.81 out of 5 average rating, 21 reviews

RV In The Keys | Tropical Retreat

Tropical retreat in the heart of Florida Keys. Relax in this fully furnished private & clean RV with parking just 30 miles from Key West. Enjoy breezy indoor/outdoor living with a fold-down patio, 2 TVs, full kitchen, bathroom, pantry. Outside seating g with awning. Nestled in a local RV park w/ pool, fish station, and coin laundry. Vacation here & swim in the ocean —Next to Pine Channel in Big Pine Key and 10 miles to Bahai Honda State Park. Walk to groceries, Walgreens, restaurants. Staycation

4.96 out of 5 average rating, 27 reviews

An aerial view showcases the beachfront location of the condominiums, with a gleaming pool surrounded by well-kept lawns. White sandy beaches meet the clear turquoise waters, while tropical palm trees sway gently in the breeze. Nearby canals and homes create a serene coastal community.

Condo in Marathon

*NEW* Private Beach, pool & fully loaded kitchen

Escape to paradise in our brand new, beautifully furnished Sun Life Vacation Homes beachfront oasis in the heart of Key Colony Beach, Florida, (some still call it Marathon). This luxurious two-bedroom, two-bathroom condominium invites you to experience the ultimate coastal retreat with private beach & pool access, tiki huts and BBQ grills. Come and experience the ultimate beachfront getaway at our Sun Life Vacation Homes, Key Colony Beach Club vacation rental. We recommend all guests purchas

4.88 out of 5 average rating, 112 reviews

A row of townhomes is positioned along the water's edge, surrounded by well-maintained landscaping. Lush green trees provide shade, and the calm water reflects the serene environment. The horizon reveals a glimpse of distant trees and open water.

Condo in Duck Key

Villa 5027 on Duck Key BOAT SLIP available

Boat slip available for additional $100 a night. Largest boat that can fit is 33 ft. Ask for availability. This villa boasts breathtaking sunsets, close to watersports, charter fishing, restaurants while being surrounded by one of the most exclusive island neighborhoods with lush landscaping. Duck Key is family-friendly, or it can be a serene couples retreat. Dine with Sunsets on the rear deck, or explore the world-class restaurants of the middle keys. Please NO Smoking indoors and NO pets.

An expansive view of a private beach is captured, showcasing gentle ocean waves lapping at the shore. Lounge chairs are arranged on a green lawn, offering relaxation options while a solitary figure strolls along the sandy beach. Palm trees frame the scene under a partly cloudy sky.

5 out of 5 average rating, 21 reviews

Private Beach in Marathons Key Colony Beach

Atlantic Ocean location with a beautiful ocean view. The beach is private for sunbathing, fishing, diving, and snorkeling. The sea life off the beach is abundant. Watching the boats come in and out of Vaca Cut is very cool. In addition to the onsite pool there is a Tiki Hut, beachside barbecue area, and a beautiful grass lawn. Being on the third floor offers beautiful ocean views. Please see my host guidebook for detailed info on a few of the local attractions including fav restaurants.

A spacious bedroom features a king bed with light bedding and decorative throw pillows. Large windows offer unobstructed ocean views and allow natural light to fill the room. A comfortable seating area is positioned nearby, facing the beach and tiki huts.

4.91 out of 5 average rating, 200 reviews

Exquisite Oceanfront Paradise - Key Colony Beach

Exquisite renovation just completed (Nov 2024). Unobstructed ocean views from our beachfront condo in Key Colony Beach. Ground floor and just a few steps away from our private beach and heated pool. Location just does not get any better. Stunning, clean white interior - kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests can enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

4.98 out of 5 average rating, 52 reviews

Grouper Getaway @ Ocean Isles Fishing Village

Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautiful brand new fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic Ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

5 out of 5 average rating, 20 reviews

Two pelicans are perched on a wooden dock, surrounded by rippling water. The dock is supported by green posts, providing a serene setting in a tropical landscape. Subtle foliage in the foreground enhances the natural ambiance of the scene.

Home in Cudjoe Key

Oceanside home 111, dock,kayaks,bikes,pool,fishing

This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. This is #111 and I also rent adjacent homes 109 and 107 in case you need more than one. We are 40 feet from the water's edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool breezes on the balconies or poolside, where you can sun, fish or boat from the docks. Key West is 17 miles away.

Apartment in Key Colony Beach

The room features two spacious beds with light-colored bedding, complemented by decorative pillows. A ceiling fan is present above, while large windows with shutters allow natural light. Colorful artwork depicting flamingos adorns the walls beside bedside tables and lamps.

5 out of 5 average rating, 15 reviews

2 Bdrm Oceanfront Complex Private Beach & Pool

Ground floor 2 bdrm/1 bath condo in Key Colony Beach. Oceanfront complex with heated pool and private white sandy beach. New renovation with new beds, furnishings and new bathroom! Condo has kitchen stocked with everything you'll need to cook & serve complete meals. You will be a 20 second walk to our private beach and enjoy glorious sunrises every morning. Lounge chairs, patio tables, tiki huts & BBQ grills available for guest use. Sorry no boats or trailers allowed in our parking lot

4.86 out of 5 average rating, 58 reviews

The living room features a spacious green sofa complemented by wicker armchairs. A glass dining table sits at the center, with light streaming through open shutters. The backdrop showcases ocean views, enhancing the connection to the balcony and natural surroundings.

Condo in Key West

Ocean front 1BR/1BA Suite w/ kitchen & living rm

1BR 1BA ocean front suite with a living room, kitchen and one bedroom. Doors that open to a balcony overlooking the Atlantic Ocean. Heated pool, hot tub, sun deck and a private sandy beach on the Atlantic ocean. 5 minutes walk to Duval street and the most Southern Point. Located between the prestigious Casa Marina and the top restaurant on the island Louise Back Yard. Free garage parking. Washer, dryers and ice maker are available for guests. Powerful, but sometimes noisy central a/c.

A spacious beachfront home is depicted, featuring a large outdoor area with neatly arranged tropical plants. A well-maintained pool is visible in the backyard, alongside a staircase leading to wraparound balconies that provide ample views of the surroundings.

4.89 out of 5 average rating, 70 reviews

Beautiful Beachfront Villa w/ Pool/Tiki/Dock

Beautiful Beachfront home located directly across the street from famous Sombrero Beach, with heated pool & Tiki Bar. Large wrap around balconies provides stunning beach views, sunrises & sunsets for relaxation. It boasts open floor plan with a large entertainment area that includes a gorgeous Olhausen Pool table, large bedrooms & the master bath is also a steam room. A 45' dock & spacious yard is great for entertaining or barbecuing. Pool Heater is available for an additional fee.

Apartment in Key Colony Beach

A shaded tiki hut with a thatched roof stands on the sandy shore, overlooking the calm, blue waters of the Atlantic Ocean. Two palm trees frame the structure, creating a serene beach environment, with gentle waves lapping at the rocks in the background.

4.85 out of 5 average rating, 131 reviews

Beachside Unit 22 - Private Beach on Atlantic

Unit 22 Details: Main Floor, Walk-in Shower, 2 Queen Beds and Queen Sofa Pull-out, Maximum Occupancy 4 Guests, Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

4.89 out of 5 average rating, 123 reviews

A cozy living space features a navy blue sofa adorned with nautical-themed throw pillows. A dining area with a glass table and chairs is visible in the background, alongside a decorative display of framed art and a potted plant. Natural light filters through the windows.

Houseboat in Marathon

Houseboat Getaway In Marathon

Get ready to indulge in a relaxing and unforgettable experience at the first overwater houseboat getaway in Marathon, Florida! 🌴🌊 What awaits you is - fun filled days living and exploring out on the fabulous florida keys waters in your own private aqualodge, breathtaking sunsets, and a private sanctuary perched above the sea. 😍 Don't miss out on this one-of-a-kind experience! Book your stay now and create memories that will last a lifetime.

Popular amenities for Big Pine Key beachfront rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Pet-friendly beachfront home rentals

New place to stay

Beach Home and Boater’s Paradise Sombrero

The image captures a sparkling private pool overlooking the water, with a sandy beach and a wooden dock in the distance. A yellow kayak is positioned nearby, and several lounge chairs are arranged by the pool, inviting relaxation under the tropical sky.

4.9 out of 5 average rating, 40 reviews

Sunset Catch Gulf Front, Pool, Dock, Kayaks, Fish

A vibrant sunset casts warm hues over the water, creating a mirror-like reflection. A wooden dock extends into the foreground, leading to the horizon, surrounded by silhouettes of trees along the shoreline. Outdoor seating is visible near the water's edge.

Home in Summerland Key

4.59 out of 5 average rating, 94 reviews

OCEAN FRONT PARADISE/ PRIVATE DOCK/AWESOME VIEWS

5 out of 5 average rating, 8 reviews

An aerial view showcases the resort's central pool surrounded by palm trees and landscaped gardens. The inviting pool area is complemented by a spacious pavilion with a metal roof, providing a gathering space. The background features the resort's accommodations and the lush natural environment.

Condo in Summerland Key

Family Suite at Sugarloaf Key Hotel (Pet Friendly)

5 out of 5 average rating, 3 reviews

A sunlit deck features white lounge chairs positioned towards a private beach and ocean view. A thatched-roof tiki hut provides shade, while a hammock is nestled nearby among greenery. The calm waters reflect the blue sky, enhancing the serene coastal setting.

Home in Islamorada

Charming Beach House directly ON the beach

Home in Upper Sugarloaf Key

A sandy beach area is framed by swaying palm trees, leading to a two-story bungalow elevated on stilts. Lounge chairs are arranged on the shore, providing a relaxing spot, while kayaks are visible in the background, enhancing the inviting beach setting.

4.74 out of 5 average rating, 98 reviews

Palm - Beach Houses Key West

A spacious houseboat is moored at the marina, featuring multiple deck levels and seating areas for relaxation. The surrounding water reflects a clear blue sky, while neighboring yachts are visible in the background. This inviting setting showcases the boat's modern design.

Houseboat in Key West

4.83 out of 5 average rating, 265 reviews

Key West Luxury Houseboat at Yacht Club Resort

A shaded outdoor porch features four blue adirondack chairs arranged around a round table, overlooking tranquil water views. The surrounding area is adorned with lush greenery and distant views of a bridge, creating a serene space for relaxation.

Townhouse in Duck Key

4.81 out of 5 average rating, 194 reviews

Vibrant Beachfront Villa

Beachfront home rentals with a pool

4.85 out of 5 average rating, 271 reviews

A spacious room features a large wooden bed with crisp white bedding. Light from a sliding glass door illuminates the space, revealing a view of palm trees and the outdoors. A ceiling fan and two bedside lamps provide ambient lighting, with a small desk and seating area visible.

Hotel room in Marathon

Wreckers House King Room - Adults Only

4.83 out of 5 average rating, 18 reviews

An aerial view of the beachfront condo building is captured, revealing its three stories and proximity to the ocean. Surrounding palm trees enhance the tropical ambiance, while the serene blue water reflects sunlight. A small parking area is visible in front of the property.

Apartment in Marathon

Seaside Villa~ Charming Beachfront Condo w/ Pool!

A spacious outdoor area features a shared pool surrounded by palm trees and lounge chairs. Umbrellas provide shade over the seating arrangements. The ocean is visible in the background, showcasing tranquil blue waters. Pathways lead to the pool area, enhancing accessibility.

Hotel room in Marathon

4.74 out of 5 average rating, 38 reviews

Breathtaking Waterfront Hotel w/ / Outdoor Pools

An outdoor balcony space features a round table surrounded by two armchairs and a spacious sofa, all in light wicker with patterned cushions. Palm trees frame the serene ocean view, creating a relaxing retreat.

Hotel room in Marathon

5 out of 5 average rating, 3 reviews

Oceanfront Balcony King, Isla Bella, Beach Resort

A private pool area features two connected sections, including a spacious swimming area and a jacuzzi. Surrounding palm trees and well-maintained landscaping create a serene atmosphere. Bright blue skies and fluffy clouds reflect on the water's surface, inviting relaxation.

Vacation home in Islamorada

Port Antigua NEW lux apart

A sandy beach scene is depicted with palm trees swaying gently in the breeze. A rainbow arches over the turquoise sea, while a wooden dock stretches into the water. Two lounge chairs are positioned near the shoreline, creating a relaxing outdoor space.

Hotel room in Layton

4.73 out of 5 average rating, 15 reviews

Amazing Beachfront Studio w/ Stunning Gulf Views!

An Olympic-sized swimming pool is surrounded by a sun deck, featuring lounge chairs and palm trees. The pool’s clear water reflects the sky, creating a serene atmosphere. The ocean and well-maintained tropical garden can be seen in the background.

Condo in Key West

4.79 out of 5 average rating, 24 reviews

Oceanfront Key West Condo

An aerial view of a condo complex along a serene beachfront. The clear blue Atlantic Ocean stretches into the distance, while a heated pool is visible in the center of the complex. Lush palm trees and well-maintained landscaping surround the buildings.

Condo in Marathon

4.83 out of 5 average rating, 6 reviews

Beachfront Condo on Coco Plum Beach w/heated pool

Private beachfront home rentals

A sandy beach area features a row of tiki huts shaded by palm leaves, offering seating for relaxation. Clear water reflects the sky and invites guests to enjoy the oceanfront setting, while a broad expanse of blue sky and billowing clouds enhances the tropical atmosphere.

4.79 out of 5 average rating, 135 reviews

Beachside Unit 36 Private Patio & Beach Plus Pool

A spacious bed is adorned with crisp white linens and a vibrant throw pillow featuring a fish design. Large windows frame the room, allowing natural light to illuminate the interior while offering views of the ocean and nearby palm trees.

4.96 out of 5 average rating, 225 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

A spacious sleeping area includes a king-sized bed with crisp white bedding and decorative pillows. Metal fish sculptures adorn the wall, complemented by two bedside lamps. A dark sectional sofa is positioned nearby, creating a comfortable seating area for relaxation.

4.92 out of 5 average rating, 305 reviews

Key Colony Beach Luxury Condo, New Modern Interior

4.93 out of 5 average rating, 256 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

A modern living area is displayed with light-colored walls and a wood-style floor. A comfortable sectional sofa and vibrant blue seating surround a circular table. A flat-screen television mounts on the wall, and natural light enters through two windows, enhancing the bright atmosphere.

4.97 out of 5 average rating, 259 reviews

Keys Breeze Ocean View Condo & Pool - Key Colony

A bright and airy bedroom features a spacious bed with crisp white bedding and decorative pillows. Nightstands with turquoise lamps flank the bed, and starfish art adorns the walls. Natural light filters through the shutters, creating a fresh and inviting atmosphere.

4.91 out of 5 average rating, 240 reviews

Poolside 2 Bdrm in Oceanfront Complex, Key Colony

The studio condo features two queen-sized beds with navy blue bedding and decorative pillows. A light grey nightstand with a lamp is positioned between the beds. A comfortable seating area and a low coffee table are visible, complemented by decorative items in muted colors.

4.94 out of 5 average rating, 249 reviews

Exquisite Luxury Oceanfront Complex Key Colony