Holiday rentals in Pigeon Key

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Top-rated holiday rentals in Pigeon Key

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Villa

4.95 out of 5 average rating, 123 reviews

Private 4/3 Pool Heater/Dock/Kayaks/Bikes,etc

Wake up to breathtaking water views at our 4-bedroom, 3-bathroom villa. Enjoy the 1800 sq ft layout, fully equipped kitchen w/stainless steel appliances, and granite countertops. Sleeps 10 with memory foam beds. Outside, relax by your private heated pool (winter) and tiki-shaded area. Fish from the 32' dock or use the BBQ gas grill. Includes 2 kayaks, 2 paddleboards, and 4 adult bikes for a 5-minute ride to Sombrero Beach. Exterior cameras for security. Vacation License #VACA-22-40. Book now!

Guest favourite

Rental unit

5 out of 5 average rating, 7 reviews

Best Catch on Grouper LN at Ocean Isles

Charming 1 bedroom / 2 bath condo just steps away from wide open views of the Atlantic Ocean. Master bedroom with private balcony and full bath upstairs. Fully equipped kitchen, living room with pull out sofa and full bath downstairs. Enjoy stunning views from the elevated heated olympic size swimming pool, fabulous oceanfront tiki huts, and fishing pier. Take your fresh catch and grill them at the air conditioned clubhouse. Don’t contemplate set that date. The fish are waiting! Keep it simple!

Guest favourite

Guest suite

4.98 out of 5 average rating, 193 reviews

Casa Mariposa: Easy walk to Sombrero Beach

***SUMMER SALE*** Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated by Forbes the #1 Airbnb for couples south of Orlando for 2024 and a top 10 Airbnb in Florida. Step from your private suite to our 50' chilled lap pool surrounded with swaying palm trees and tropical foliage, large coral stone patio, and extensive tropical gardens. Avoid beach parking fees at beautiful Sombrero Beach with a short stroll from your suite at Casa Mariposa!

Guest favourite

Apartment

4.96 out of 5 average rating, 194 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.

Guest favourite

Home

4.91 out of 5 average rating, 11 reviews

1 Free Night-Ask Us How - Tropical Private Home

License# VACA-23-370.Conch cottage located in the Heart of Marathon. Home sits on 8,000+ sf lot w/2 bed (king in main BD & 2 twins in 2nd BD) 1 bath SF home with fully equipped kitchen & full bath w/shower & tub + a lot of natural light and garden view all around. W/D, brand new mini split ACs in living room, & both bedrooms, back deck has a BBQ, Hot Tub & huge yard w/plenty of parking for a boat and trailer. ******1 FREE NIGHT, ASK US HOW******Hot Tub, BBQ. Bring Your Boat, RV Parking

Guest favourite

Guest suite

4.99 out of 5 average rating, 93 reviews

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

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite 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. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

Superhost

Villa

4.91 out of 5 average rating, 223 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

Home

4.99 out of 5 average rating, 119 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Guest favourite

Home

4.98 out of 5 average rating, 48 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Guest favourite

Apartment

4.92 out of 5 average rating, 130 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with Shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and 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.”

Guest favourite

Houseboat

4.89 out of 5 average rating, 97 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

4.98 out of 5 average rating, 53 reviews

Waterfront Oasis: Pool, Tiki Lounge, Dock & BBQ

Discover your dream vacation in this freshly remodeled 3-bedroom, 2-bath gem on a stunning flow-through canal with direct ocean access right from your dock. Perfect for a memorable Keys getaway, this tropical retreat features a private pool, tiki lounge, grill, ice maker, and a fish cleaning station—all set in a spacious backyard designed for relaxation and fun!