Holiday rentals near Blue Hole

We found 1,271 holiday rentals — enter your dates for availability

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November 2025

December 2025

Find the perfect holiday home that's near Blue Hole. Holiday homes offer the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Blue Hole

Showing deals for:30 Jan - 6 Feb

Exceptional

(35 reviews)

34’ Catamaran Sailboat

Key West, FL

8% off

for 7 nights, 1 houseboat

NZ$622 per night

includes taxes & fees

Exceptional

(53 reviews)

Luxury Ocean View 2 Bed / 2.5 Bath Townhome in the Keys

Summerland Key, FL

8% off

for 7 nights, 1 home

NZ$1,089 per night

includes taxes & fees

Exceptional

(12 reviews)

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Summerland Key, FL

8% off

for 7 nights, 1 cottage

NZ$671 per night

includes taxes & fees

Stretch out in the comfy living room space-appointed with new pull out sectional

Exceptional

(9 reviews)

WATERFRONT Seaside Sanctuary in the Keys with 35' SEAWALL FOR YOUR BOAT!

Summerland Key, FL

8% off

for 7 nights, 1 home

NZ$1,069 per night

includes taxes & fees

Exceptional

(87 reviews)

Bay View 2 Bed / 2.5 Bath Vacation Townhome Rental in Key West Area

Summerland Key, FL

8% off

for 7 nights, 1 home

NZ$1,089 per night

includes taxes & fees

Exceptional

(31 reviews)

Connecting 2 Bed / 2.5 Bath Luxry Townhomes w/Seperate Entrances - Can Sleep 12

Summerland Key, FL

8% off

for 7 nights, 1 home

NZ$2,136 per night

includes taxes & fees

Exceptional

(35 reviews)

2 Bedroom 2.5 Bath Luxury Townhome in the Keys

Summerland Key, FL

8% off

for 7 nights, 1 home

NZ$1,089 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Blue Hole

Old Wooden Bridge Resort and Marina

Sleeps 6 · 2 bedrooms

Old Florida Style, wrap around porch, boat basin for dockage, open water

Sleeps 6 · 3 bedrooms · 2 bathrooms

Premier Host

Upscale Luxury House on Open Water Gated Community, Dock, Pool, Kayaks, Bikes

Sleeps 6 · 2 bedrooms · 3 bathrooms

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West

Sleeps 4 · 2 bedrooms · 2 bathrooms

One of the very few beach houses with a daily, rental license in the Keys.

Sleeps 12 · 4 bedrooms · 3 bathrooms

Top rated rentals - Blue Hole

Cozy Cottage dock for fishing, snorkeling, and relaxing.

Premier Host

Cute cottage

We had a great stay Great neighbourhood Nice place

Miranda H.

Stayed Jan 2020

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value