Holiday rentals in West Summerland Key

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Top-rated holiday rentals in West Summerland Key

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Superhost

Tiny home in Big Pine Key

4.81 out of 5 average rating, 196 reviews

Cheerful Tiny House in the Florida Keys

Enjoy your trip to the keys by staying at this wonderful tiny house, surrounded by nature and deers! This is a hidden gem in the keys for your relaxation, enjoyment. Cozy and roomy space for the whole family! The Tiny house is located in the small Breezy Pines RV Resort. It has everything you would need during your trip. Outdoor patio area with rattan sofa and armchairs, grill offer an additional comfort for incredible vacation! it has everything for your nice and comfy stay close to Key West!

Guest favourite

Tiny home in Big Pine Key

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 favourite

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!

Guest favourite

Apartment in Key Colony Beach

4.96 out of 5 average rating, 208 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Superhost

Boat in Marathon

4.79 out of 5 average rating, 272 reviews

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.

Guest favourite

Cottage in Little Torch Key

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!

Guest favourite

Home in Key Colony Beach

4.95 out of 5 average rating, 117 reviews

Waterfront Home 37.5-ft dock, Cabana Club Included

Bright, Open Floor Plan with new floors & kitchen. East facing for sunny mornings and shady afternoons on the great screened porch. Two roomy bedrooms and 2 full baths. Plenty of parking on the paved driveway. Perfectly located with the boater and angler in mind on a 37. 5 ft concrete dock, on deep & wide canal. Here on Key Colony Beach you can walk or bike the entire city to the marina, Sunset Park, 3 restaurants, play golf, tennis, pickle ball, bocce ball, horseshoes & basketball.

Superhost

Campervan/Motorhome in Big Pine Key

4.85 out of 5 average rating, 67 reviews

The Island Gypsy

Reconnect with nature at this unforgettable escape. Property butts up to the endangered Key deer refuge with almost daily sightings in the yard. Only 6 miles offshore is Looe key and the 3rd largest reef in the world. Our lot has parking for 2 vehicles with a outdoor dining area and large backyard for hanging out. The island gypsy is our 5th wheel which sleeps 4 with a queen bed, queen bunk beds and a sofa bed. Heated pool in the park and right across street from clubhouse.

Guest favourite

Villa in Marathon

4.91 out of 5 average rating, 322 reviews

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

This hip spot is the new thing in lodging. Aqua Lodge is all the modern amenities while being on the water. Full kitchens, flat screen tv's, wi-fi , pool, bikes, sunset beach. We have it all right at your finger tips. You can sleep up to 5 people comfortably. We have great air conditioning and big showers. The deck is furnished with a dining table for those romantic outdoor dinners in the moonlight. We also have a sunset beach area for the best sunsets in the Florida keys!

Guest favourite

Houseboat in Marathon

4.89 out of 5 average rating, 120 reviews

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.

Guest favourite

Home in Cudjoe Key

4.93 out of 5 average rating, 178 reviews

106 Newly Renovated House with Oceanview and Pool

"This three-story home overlooks the Atlantic ocean in a gated community of only 10 other homes. Just south enough to enjoy the bluest water in the keys and only 20 minutes away from Key West! This pristine home sleeps 6 comfortably and makes a great destination to exploring all the wonders the FL Keys. Come enjoy the pool, fishing, boating, diving or just relax with the ocean breeze. This location has all the best of the Keys."

Guest favourite

Campervan/Motorhome in Big Pine Key

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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Other great holiday rentals in West Summerland Key

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!

Campervan/Motorhome in Big Pine Key

4.8 out of 5 average rating, 5 reviews

Glamping in the Keys

JeffreyRating, 5 stars1 week ago

A1 place to stay! Ms Donna is a great host!

Holiday 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!

Superhost

Home in Marathon

New place to stay

Grand Blue Arenas/ 120'Dock/Mini golf/GameRoom

ArielRating, 5 stars2 weeks ago

hard to find a house like this in marathon. excellent value for the most exclusive area. very comfortable and with everything you need to spend unforgettable days with your family

Cabin in Marathon

4.9 out of 5 average rating, 10 reviews

New Waterview Cabins w Boat Ramp

RassulRating, 5 stars1 week ago

Boat docks , canal is shallow need to be careful, nice piece full place very good nice people stuff

Guest favourite

Home in Big Pine Key

5 out of 5 average rating, 6 reviews

Cozy Waterfront Key Deer Retreat

KatherineRating, 5 stars1 month ago

Beautiful, Beautiful Beautiful did I say Beautiful. you won't be disappointed if you rent this house, so private and quiet. yes the neighbors are close but they weren't home our entire stay and we wouldn't have noticed if they were there, there was to much to do and see. So easy and close to a marina to put your boat in the water for 10$ each day In and Out. The Rooster was perfect for many dinners. Boondocks 10 minutes away for a little competitive putt putt, live music,and great food. Shopping galore Key West just 30 minutes away. Oh yes and the house was Beautiful, the beds were comfy, extremely clean and everything to make your vacation great is right here. The Key Deer are a bonus. Thank you Estrella we will be back.

Flat in Marathon

4.61 out of 5 average rating, 844 reviews

Standard 1 Bedroom King Suite with Balcony

CarolinaRating, 5 stars2 weeks ago

My boyfriend & I have been coming to Skipjack for his birthday for the last two years & we absolutely love it ! It has become a little tradition. We love the space and the dock in the back! During our stay we saw a manatee, a Manta Ray, & lots of Tarpon in that canal. Absolutely beautiful. The location couldn’t be better as it’s right in marathon, where you are close to Sombrero Beach, Publix, lots of delicious restaurants with great ambience, etc! We look forward to our next stay at SkipJack!! :)

Guest favourite