Vacation rentals in Blue Hole

4.93 out of 5 average rating, 129 reviews

Cottage in Cudjoe Key

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.

Tiny home in Big Pine Key

A modern washing machine is showcased beside a stainless steel countertop. A glass container labeled 'Homemade Laundry Soap' is placed nearby. Natural light filters through sheer curtains, enhancing the functional space.

4.93 out of 5 average rating, 76 reviews

Tiny Fish Haus

Come experience Tiny Home Living in this Park Model RV right next to the National Key Deer Refuge! . Relax on our covered patio next to a large Saltwater Swimming Pool, Cook dinner on a Blackstone grill , enjoy WIFI, Games, a Flat Screen TV , we have Premium Organic Bedding on our Queen beds for comfort. Turkish Towels for bath and beach..explore Big Pine Key with our 2 bicycles that are included .AirPurifier for clean air inside. 28 Miles to Key West. Keys Shuttle located next to our park

Top guest favorite

A thatched-roof building is seen surrounded by lush palm trees and colorful tropical plants. A clear sky is visible above, and a vehicle is parked in the driveway, indicating convenient access to this vibrant establishment.

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 109 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, Turtle-by-the-Sea is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home. Shoot us a message & start planning your dream Keyscation!

A serene beachfront scene showcases two palm trees framing a vibrant sunset over the water. The horizon is painted with soft hues of orange and purple, while the shoreline features sandy terrain leading to the calm sea.

4.73 out of 5 average rating, 106 reviews

Tropical RV Getaway in Big Pine Key

Cozy RV is located on Big Pine Key where the endangered Key Deer roam. It is the perfect location! Located near a bike path that leads to restaurants, shops, bars, grocery store and beautiful waterfront park. Close to lots of Swimming, Snorkeling, Diving, Kayaking and Fishing. Just a short drive to Key West, Marathon, Bahia Honda State Park and National Key Deer Refuge. Great fishing spots nearby! Relax and unwind with a game of Connect 4 or Ring Toss in fenced in private backyard.

4.79 out of 5 average rating, 273 reviews

A modern houseboat is anchored on calm waters during sunset. The structure features large windows and a spacious front deck with a grill station. The warm glow of the setting sun illuminates the exterior, reflecting off the water, creating a serene atmosphere.

Boat in Marathon

Paradise awaits on this cozy houseboat!

Our vision is for you to kick back, relax, and find your home away from home! Wether you want to celebrate with your loved one or retreat by yourself this floating home offers comfortable space for 2 adults. Located near the 7 mile bridge in Marathon Florida on the Atlantic Ocean nestled in a quiet, reserved mangrove area. This spot is fantastic because you have unparalleled access to out of this world sunset/sunrise views. Kayak through the mangrove and explore the surrounding areas.

Cottage in Little Torch Key

A long wooden dock extends into clear blue water, flanked by palm trees and lush greenery. Two turquoise chairs are positioned at the dock’s end, providing an ideal spot for relaxation and enjoying scenic water views under a bright sky dotted with clouds.

4.9 out of 5 average rating, 167 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!

An aerial view showcases the expansive resort area featuring a large swimming pool surrounded by lounge chairs. The vibrant blue water extends beyond the pool, with palm trees swaying gently in the breeze. Nearby, a shaded pavilion offers a gathering space with pathways leading toward additional amenities.

4.86 out of 5 average rating, 98 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!

4.97 out of 5 average rating, 160 reviews

Cudjoe Key Home with a View

We are so excited to share our little piece of paradise with you! Our unit is located a short walk away from all the amenities the Venture Out community has to offer such as a pool, hot tub, lagoon, bocce ball, tennis courts, playground and boat marina. On the property we have a 2-person hybrid kayak for your enjoyment. We also provide table games (we love a game night) as well as the equipment to play bocce ball and darts which can be played in the recreation center.

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.

4.83 out of 5 average rating, 265 reviews

OCEAN PARADISE AT VENTURE OUT + 4 BIKES/ 2 KAYAKS!

*PERFECT LOCATION! * 35' Seawall *AWWSOME 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!

Top guest favorite

A serene waterway is depicted with turquoise waters reflecting the sky. Palm trees are visible along the shore, framing nearby buildings. A wooden post is anchored at the forefront, suggesting a space for docked boats and enhancing the tranquil coastal atmosphere.

Home in Key Colony Beach

4.94 out of 5 average rating, 118 reviews

Paradise in Key Colony Beach + Cabana Club

Beautiful two bedroom, two bathroom property in the prestigious Key Colony Beach neighborhood. This property is a ten minute walk from Sunset Beach, two minute walk from restaurants and bars in KCB and across the street from a golf course, tennis court and playground. Dockage for boats up to 50ft and beautiful water views. Key Colony Beach Cabana Club is included with your stay. You'll feel completely relaxed in this tropical oasis.

An outdoor patio is seen overlooking crystal-clear waters, featuring a charcoal grill and a view of the expansive ocean. Potted plants with vibrant flowers enhance the area, while a railing provides safety along the water's edge, inviting relaxation and enjoyment.

4.9 out of 5 average rating, 107 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.

A printed document outlines various regulations and information related to the Breezy Pines RV Estates Condominium Association. Sections cover topics such as door codes, facilities, restrooms, showers, laundry, rules for guests, and rental guidelines. Contact numbers for maintenance and management are also provided.

4.9 out of 5 average rating, 83 reviews

Having fun in the lower Keys

Enjoy the lovely setting of this romantic spot in nature. Big Pine Key is in the center of the lower Keys just 35 miles from Key West making it convenient to all the tourism and night life adventure the Keys have to offer while simultaneously being far enough away to allow for an off the beaten path relaxing experience. I have left several destinations for diving , fishing and/or great spots to just relax and take in the sun.

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Popular amenities for Blue Hole vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Blue Hole

A bright living space features large windows with light-filtering shutters, offering a view of the outside. A spacious day bed is positioned near the windows, complemented by a rustic dining table and chairs. The adjacent kitchen includes modern appliances, enhancing the open layout.

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars3 weeks ago

The cabin was cozy and super cute. It was impeccably clean. I only stayed one night but wish I stayed longer. She had all the necessary amenities. I didn’t get to use the patio since I mostly stayed out on the boat but wish I had more time to do so. Kristin had board games, shampoo, conditioner, body wash, blow dryer, washer, dryer and everything you would want in an AirBNB. There are plenty of restaurants nearby and the supermarket wasn’t too far. I felt safe in the neighborhood. I hope to come back and stay here again!

A bathroom area is featured with wooden cabinetry and a white countertop. A mirror is above the sink, reflecting the light. The shower area is partially visible, with hooks for towels and a small basket for toiletries mounted on the wall.

4.6 out of 5 average rating, 25 reviews

Tiny home in RV park with pool

HermesRating, 5 stars1 month ago

Everything was good and I recommend it

A modern RV is parked in front of a vibrant blue home, showcasing a well-maintained yard with palm trees and gravel. The house features large windows and a contemporary design, offering a sense of spaciousness and outdoor living. The setting highlights a relaxed, coastal atmosphere.

Vacation home in Big Pine Key

5 out of 5 average rating, 5 reviews

Boater dream home 75ft wide crystal clear canal

KathyRating, 5 stars14 months ago

My husband and I, along with some friends, stayed the month of March. The description of the house is accurate; clean, homey, comfortable beds, nice furnishings and decorated nicely. A few minor issues came up while we were there and Kelly & Walter responded very quickly to resolve! We kayaked/paddle board with manatees in the canal right outside our front door, to include different kinds of fish. I enjoyed my morning runs on the bike/walking trail at the end of our street. Also, met many nice neighbors as well while walking our dog. The weather was beautiful, only rained 3 days the entire time we were there. The boat lift and pool were a plus, after a day of boating we would come back and cool off in the pool. We enjoyed our stay so much, we have already booked March of next year!!! Thank you Kelly & Walter for sharing your home with us!

Condo in Key West

4.89 out of 5 average rating, 87 reviews

Ocean Front Suite with Direct Beach Access

LaurenRating, 5 stars2 days ago

Loved the place, worth the price! Beautiful views, lots of space in the suite.

A shaded outdoor area features a hammock positioned between two columns, inviting relaxation. The stone flooring spans the space, leading to a tranquil pool with open water views visible beyond. Palm trees sway gently in the background, enhancing the peaceful ambiance.

Home in Summerland Key

5 out of 5 average rating, 4 reviews

A month in paradise pool home.

LOUISERating, 5 stars10 months ago

We spent a month at this beautiful home. From open water the view, to the boating access, the amazing sunset and the pool, the place was perfect for us! We love the lower keys and this was the ideal place to spend a month. Tracy was always responsive answering any questions we had. I can't recommend enough. We hope to return in the future!

A close-up image of a Key Deer, displaying its gentle features. The deer is positioned in a natural outdoor environment, surrounded by brown earth and green foliage. Its large eyes and prominent nose are highlighted, capturing a curious expression as it gazes forward.

4.71 out of 5 average rating, 14 reviews

RV In The Keys | Tropical Retreat

TalitaRating, 5 starstoday

We had a fantastic stay at for our anniversary! The trailer was filled with everything you need during your stay — we cooked dinner, hung out, watched TV, and had a great night of sleep. It was very accommodating, especially since we brought along our two dogs. The location was perfect, and we appreciated how pet-friendly and welcoming everything was. And how close it was to anything we needed it. One of the most memorable parts of our trip was being able to get super close to the local baby deer. They were incredibly friendly and loved the attention — a truly special experience that we’ll never forget. We booked this place to spend Saturday at the sandbar at Content Key, which was absolutely a dream — phenomenal place that made our trip extra memorable. Heather was incredibly responsive and helpful, providing us with all the information we needed for a smooth and enjoyable stay. Highly recommend for anyone looking for a relaxing getaway in Big Pine Key. We can’t wait to return!

The exterior of the townhome showcases a well-maintained pool surrounded by a spacious deck. Several lounge chairs are positioned near the water, while palm trees provide shade. The building features a combination of stone and wooden elements, with large windows inviting natural light.

Townhouse in Little Torch Key

4.77 out of 5 average rating, 91 reviews

Waterfront 2BD / 2.5BTH Luxury Townhome

AlexRating, 5 stars1 month ago

Wonderful place to stay and great location for multiple key adventures throughout your stay. My family and I enjoyed the stay. We will definitely stay with little torch cottages again!