Holiday rentals in Saddlebunch Keys

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.

4.97 out of 5 average rating, 145 reviews

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

4.8 out of 5 average rating, 270 reviews

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.

4.97 out of 5 average rating, 259 reviews

Home in Key West

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!

Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, newly renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, tumbled marble 2 person shower, private front deck with seating for 4 and 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.

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!

4.97 out of 5 average rating, 100 reviews

Apartment in Key West

Hidden Beach unit 1 The Perfect Place to stay

This place is extraordinary. There is nothing like it in Key West. Just 3 blocks from Duval Street, this property sits on Key West’s only natural beach. Hidden Beach is right on the Atlantic Ocean nestled between Key West’s best restaurant (Louie’s Backyard) and the beautiful, luxurious Reach Resort.Here, you can enjoy spectacular views and sunsets from one of the islands only private beaches or you can stroll through Old Town, an amazing architectural and botanical treasure.

4.91 out of 5 average rating, 320 reviews

Villa in Marathon

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!

4.97 out of 5 average rating, 159 reviews

Home in Cudjoe Key

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.

4.93 out of 5 average rating, 178 reviews

Home in Cudjoe Key

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."

4.97 out of 5 average rating, 106 reviews

Home in Key Largo

The Paradise 2

Relax with the whole family at this peaceful place to stay. Our home is located right by the water. Modern spacious and spotless with private parking, fast Wi-Fi, cold AC plus cozy beds and pillows in every bed. Relax on the waterfront patio chairs, swim in our newly renovated pool, watch the manatees and dolphins swim by and go fishing from our backyard dock anytime. We are sure you will absolutely love our Tiny Home!

4.96 out of 5 average rating, 280 reviews

Flat in Key West

Poolside Truman Annex 2 Bed | Conch Life Condo

Cozy condo in the Truman Annex to fully experience the conch life. It is close to Fort Zachery Beach and State Park, Hemingway House, Mallory Square, and Duval Street. Location is perfect due to Island proximity to any event and occasion. My place is a great getaway for couples, solo adventurers, business travelers, and families (with kids).

4.87 out of 5 average rating, 246 reviews

Houseboat in Key West

Key West Luxury Houseboat at Yacht Club Resort

2x Queen Bedrooms 2x Ensuite Full Bath Queen Sleeper Sofa and 1/2 Bath PANORAMIC Ocean Views 200+ FIVE STAR Reviews- FIVE YEARS SuperHost Rated ~ SUN DECKS on All Levels, HUGE SKY Deck Rooftop Ocean-View Living Room ~ Floor-to-Ceiling Windows ~ 50 inch TV ~ Granite Countertops Throughout ~Full Kitchen, Full Size Appliances ~

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Other great holiday rentals in Saddlebunch Keys

4.95 out of 5 average rating, 19 reviews

Houseboat in Key West

Shanty Pineapple Key West

KirstieRating, 5 stars1 week ago

Thanks to Tony for making our stay at the Shanty Pineapple was a wonderful experience! Everything was clean and how it was described in the listing! We had a great time celebrating our anniversary! The view of the sunrise and sunset each day was amazing! And the food delivery was extremely convenient! Thanks again Tony! Highly recommend!

4.8 out of 5 average rating, 15 reviews

Home in Little Torch Key

Indulge yourself. It's heavenly in Little Torch

CharlesRating, 5 stars3 months ago

Clean and neat home on a quiet canal. Neighbors were even friendly! Good amount of parking. Home is clean and well laid out. Airy living room just off the open kitchen. Large master bedroom and bathroom. We felt very comfortable there.

Home in Summerland Key

4.82 out of 5 average rating, 57 reviews

Kelly’s Kabin - Private FL Keys Cottage

LadyRating, 5 stars2 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!

5 out of 5 average rating, 7 reviews

Flat in Key West

Duval Corner - Pet friendly with Balcony

JulianRating, 5 stars2 weeks ago

Beautiful little apartment right on Duval Street. Really was a small slice of paradise.

Apartment in Key West

4.91 out of 5 average rating, 82 reviews

Ocean Front Suite with Direct Beach Access

TerrenceRating, 5 stars1 week ago

It was a wonderful experience and the amenities and staff were great! Will 100% recommend the on site restaurants dinner menus (PRIME RIB!!). The 24 hr pool and hot tub access were also a nice touch. Allowed us to enjoy water activities during the day, and some cooler experiences in the evening away from the sun!

4.9 out of 5 average rating, 30 reviews

Home in Cudjoe Key

Waterfront FL Keys Cottage @ Venture Out

MariaRating, 5 stars2 weeks ago

What a beautiful cottage. Loved how it was decorated. We had everything that we needed. Loved the outside back patio. Peaceful and quiet. The bed was super comfortable. Very clean and a plus, it had a washer and dryer. Thomas and Lindsay were so nice, communicative and very responsive. Gave us some great recommendations on restaurants and things to do in the area. A little piece of paradise. Island Life. We will DEFINITELY be back. Highly recommend.

5 out of 5 average rating, 39 reviews

Tiny home in Key Largo

Oasis3 Ocean View Luxury Tiny House

KayleighRating, 5 stars1 week ago

This was a beautiful place to stay! This was our third time staying at one of Blanca’s properties in the Keys and we enjoy ourselves every time. Our kids loved fishing off the dock and we loved being able to bring our boat with us. Some of our favorite restaurants are also less than 20 minutes away. We loved our time here and can’t wait to be back.