Cutthroat Harbor Estates vacation rentals
We found 299 vacation rentals — enter your dates for availability
Discover a selection of 73 homes and other vacation rentals in Cutthroat Harbor Estates that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the best amenities for spending time at your home away from home, which might include WiFi and a fireplace. Whatever you're looking for, you're sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.
Vacation rentals with weekly discounts - Cutthroat Harbor Estates
Showing deals for:Nov 7 - Nov 14
Image gallery for Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
9.89.8 out of 10 rating
Exceptional
(236 reviews)
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Summerland Key, FL
10% off
Price is CA $557
CA $557
CA $5,309 total
CA $5,309 total
includes taxes & fees
Image gallery for OCEANIA... water front cottage retreat ~
9.89.8 out of 10 rating
Exceptional
(6 reviews)
OCEANIA... water front cottage retreat ~
Summerland Key, FL
7% off
Price is CA $894
CA $894
CA $8,022 total
CA $8,022 total
includes taxes & fees
Image gallery for 20 MINUTES TO KEY WEST , BOATERS PARADISE
9.49.4 out of 10 rating
Exceptional
(57 reviews)
20 MINUTES TO KEY WEST , BOATERS PARADISE
Summerland Key, FL
10% off
Price is CA $284
CA $284
CA $2,495 total
CA $2,495 total
includes taxes & fees
Image gallery for water at your back door
8.88.8 out of 10 rating
Excellent
(34 reviews)
water at your back door
Summerland Key, FL
10% off
Price is CA $390
CA $390
CA $3,583 total
CA $3,583 total
includes taxes & fees
Image gallery for Tropical Island Paradise W / Open Water Views!
9.69.6 out of 10 rating
Exceptional
(104 reviews)
Tropical Island Paradise W / Open Water Views!
Summerland Key, FL
10% off
Price is CA $334
CA $334
CA $3,103 total
CA $3,103 total
includes taxes & fees
Image gallery for Lower Keys paradise
1010 out of 10 rating
Exceptional
(34 reviews)
Lower Keys paradise
Summerland Key, FL
10% off
Price is CA $303
CA $303
CA $2,879 total
CA $2,879 total
includes taxes & fees
Image gallery for Emerald Seas - Florida Keys Ocean Front Paradise!
1010 out of 10 rating
Exceptional
(18 reviews)
Emerald Seas - Florida Keys Ocean Front Paradise!
Summerland Key, FL
10% off
Price is CA $805
CA $805
CA $7,208 total
CA $7,208 total
includes taxes & fees
Image gallery for Island Therapy
9.89.8 out of 10 rating
Exceptional
(58 reviews)
Island Therapy
Summerland Key, FL
10% off
Price is CA $334
CA $334
CA $3,103 total
CA $3,103 total
includes taxes & fees
Image gallery for Relax by Florida Keys Beaches, just a 7-min drive away
9.89.8 out of 10 rating
Exceptional
(194 reviews)
Relax by Florida Keys Beaches, just a 7-min drive away
Summerland Key, FL
10% off
Price is CA $310
CA $310
CA $2,890 total
CA $2,890 total
includes taxes & fees
Image gallery for Fishermen’s Paradise
9.29.2 out of 10 rating
Wonderful
(97 reviews)
Fishermen’s Paradise
Summerland Key, FL
10% off
Price is CA $303
CA $303
CA $2,870 total
CA $2,870 total
includes taxes & fees
Image gallery for Waterfront RV Lot w 35' dock in "Venture Out". Utility hookups & beautiful views
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Waterfront RV Lot w 35' dock in "Venture Out". Utility hookups & beautiful views
Summerland Key, FL
10% off
Price is CA $136
CA $136
CA $1,191 total
CA $1,191 total
includes taxes & fees
Image gallery for Paradise in the Lower Keys!
8.68.6 out of 10 rating
Excellent
(19 reviews)
Paradise in the Lower Keys!
Summerland Key, FL
7% off
Price is CA $352
CA $352
CA $3,584 total
CA $3,584 total
includes taxes & fees
Image gallery for A slice of paradise
9.09.0 out of 10 rating
Wonderful
(96 reviews)
A slice of paradise
Summerland Key, FL
10% off
Price is CA $266
CA $266
CA $2,549 total
CA $2,549 total
includes taxes & fees
Image gallery for ATLANTIS...Ocean Front Cottage Retreat!
9.89.8 out of 10 rating
Exceptional
(13 reviews)
ATLANTIS...Ocean Front Cottage Retreat!
Summerland Key, FL
7% off
Price is CA $1,150
CA $1,150
CA $10,287 total
CA $10,287 total
includes taxes & fees
Image gallery for Sun Bake @ Sponge Cake, 64' Sea Wall,
9.69.6 out of 10 rating
Exceptional
(20 reviews)
Sun Bake @ Sponge Cake, 64' Sea Wall,
Summerland Key, FL
5% off
Price is CA $386
CA $386
CA $3,587 total
CA $3,587 total
includes taxes & fees
Image gallery for NAUTILUS...ocean front cottage retreat ~
8.88.8 out of 10 rating
Excellent
(6 reviews)
NAUTILUS...ocean front cottage retreat ~
Summerland Key, FL
10% off
Price is CA $742
CA $742
CA $6,707 total
CA $6,707 total
includes taxes & fees
Image gallery for Crystal Clear Water Getaway!
9.89.8 out of 10 rating
Exceptional
(70 reviews)
Crystal Clear Water Getaway!
Summerland Key, FL
10% off
Price is CA $310
CA $310
CA $2,898 total
CA $2,898 total
includes taxes & fees
Image gallery for Waterfront home with numerous amenities on popular Cudjoe Key!
9.49.4 out of 10 rating
Exceptional
(18 reviews)
Waterfront home with numerous amenities on popular Cudjoe Key!
Summerland Key, FL
20% off
Price is CA $248
CA $248
CA $2,483 total
CA $2,483 total
includes taxes & fees
Image gallery for Springs Venture Out Dolphin House (#386) with beautiful open water views
9.49.4 out of 10 rating
Exceptional
(98 reviews)
Springs Venture Out Dolphin House (#386) with beautiful open water views
Summerland Key, FL
10% off
Price is CA $310
CA $310
CA $2,890 total
CA $2,890 total
includes taxes & fees
Image gallery for 35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
9.89.8 out of 10 rating
Exceptional
(129 reviews)
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Summerland Key, FL
10% off
Price is CA $358
CA $358
CA $3,602 total
CA $3,602 total
includes taxes & fees
Image gallery for Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
9.49.4 out of 10 rating
Exceptional
(159 reviews)
Comfortable Waterfront Vacation Rental minutes from key west w boat dock 35 ft
Summerland Key, FL
7% off
Price is CA $230
CA $230
CA $2,203 total
CA $2,203 total
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Cutthroat Harbor Estates
Beautifully Renovated with Stunning Sunset Views and Dockage!
Sleeps 8 · 3 bedrooms · 2 bathrooms
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Sleeps 6 · 3 bedrooms · 2 bathrooms
8.48.4 out of 10
Very goodvery good
114 reviews(114 reviews)
Grand Opening! New Construction in Venture Out! 3 night minimum stay.
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Secluded Oceanfront property, Private pool, hot tub, boat ramp and dock
Sleeps 7 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
A slice of paradise
Sleeps 6 · 3 bedrooms · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
96 reviews(96 reviews)
Gasparilla Villa - Your Ocean View Oasis on Cudjoe Key - Sunset Views!
Sleeps 6 · 3 bedrooms · 2 bathrooms
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of vacation rental in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, vacation houses are the most popular type of rental, with around 65 available in the area. These homes typically feature spacious layouts, multiple bedrooms, and fully equipped kitchens, making them ideal for families or groups. Many also include outdoor areas such as private patios or balconies where guests can enjoy the warm Florida weather and scenic views. Additionally, there are several cottages and apartments available, providing even more options for travellers seeking a comfortable stay.
Are there any beach house rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, Florida, there are about 84 beach house vacation rentals available, offering a variety of options for travellers. These properties are typically located in serene neighbourhoods with easy access to the waterfront, making them ideal for those looking to enjoy the natural beauty of the area. Most beach houses come equipped with essential amenities such as fully furnished kitchens, spacious living areas, and outdoor patios or decks, great for relaxing and soaking up the sun.
How much does it cost to rent a vacation home in Cutthroat Harbor Estates?
Prices for vacation rentals in Cutthroat Harbor Estates vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Cutthroat Harbor Estates to more spacious homes.
Are there any discounts for Cutthroat Harbor Estates vacation house rentals?
You can find great discounts on house rentals in Cutthroat Harbor Estates on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Are there any Cutthroat Harbor Estates vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Cutthroat Harbor Estates with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Can I find long-stay vacation rentals in Cutthroat Harbor Estates?
A long-stay vacation rental in Cutthroat Harbor Estates is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
When is the best time to visit Cutthroat Harbor Estates for a vacation rental?
The best time to book a vacation rental in Cutthroat Harbor Estates is during the peak season from July to September, with September being particularly popular. This is when the weather is at its finest, offering warm temperatures around 30°C, superb for outdoor activities and relaxation by the water. Visitors flock to the area to enjoy fishing, kayaking, and exploring the beautiful coastal scenery, making it a vibrant time to experience the local culture and natural beauty.
In September, the crowds begin to thin slightly, allowing for a more laid-back atmosphere while still enjoying the summer warmth. This month strikes a lovely balance, providing ample opportunities for sightseeing and water-based adventures without the peak season congestion.
For those looking for a more budget-friendly option, consider planning your visit in November. While this month is quieter, it still offers a chance to enjoy the tranquil surroundings and the natural beauty of the area, making it an excellent time for peaceful walks and wildlife watching.
Are there any remote work vacation rentals in Cutthroat Harbor Estates?
In Cutthroat Harbor Estates, there are numerous remote work vacation rentals available, with around 51 options to choose from. This tranquil area in Florida is great for those looking to balance work and leisure. Many properties are equipped with essential amenities for remote work, including high-speed Wi-Fi, dedicated office spaces, and ergonomic desks and chairs. Some rentals even come with additional features like safe storage for valuables and computer monitors, ensuring a productive workspace. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Cutthroat Harbor Estates vacation rental?
Book your Cutthroat Harbor Estates vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.
*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Can I change or cancel my Cutthroat Harbor Estates home rental booking on Vrbo?
To find Cutthroat Harbor Estates vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.
Are all fees included in the Cutthroat Harbor Estates vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.