Holiday rentals near Old Road Gallery
We found 2,616 holiday rentals — enter your dates for availability
If you are looking to stay near Old Road Gallery, take a look at private holiday rentals to find the perfect one for your trip. Whether you’re staying in a holiday home with family or friends, you'll find the best amenities for hanging out with the people that matter most, which might include a fireplace and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Old Road Gallery
Showing deals for:26 Sept - 3 Oct
Image gallery for Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
9.69.6 out of 10 rating
Exceptional
(27 reviews)
Bungalow #4 - 2 Bed/1 Bath & Pool in Islamorada
Islamorada, FL
8% off
Price is NZ$5,379
NZ$5,379
NZ$768 per night
includes taxes & fees
Image gallery for Fun For All! Key Largo 3/3 Townhome Oceanside Resort
9.69.6 out of 10 rating
Exceptional
(59 reviews)
Fun For All! Key Largo 3/3 Townhome Oceanside Resort
Key Largo, FL
8% off
Price is NZ$4,993
NZ$4,993
NZ$713 per night
includes taxes & fees
Image gallery for Oceanfront, 2 Pools, Lagoon, Tennis, Picketball, Marina, Fishing & Great Views!
9.89.8 out of 10 rating
Exceptional
(128 reviews)
Oceanfront, 2 Pools, Lagoon, Tennis, Picketball, Marina, Fishing & Great Views!
Key Largo, FL
14% off
Price is NZ$6,586
NZ$6,586
NZ$941 per night
includes taxes & fees
Image gallery for TOWNHOUSE FL KEYS ON ATLANTIC, MARINA, PICKLEBALL, TENNIS, POOLS, BIKES, KAYAKS
9.69.6 out of 10 rating
Exceptional
(63 reviews)
TOWNHOUSE FL KEYS ON ATLANTIC, MARINA, PICKLEBALL, TENNIS, POOLS, BIKES, KAYAKS
Key Largo, FL
8% off
Price is NZ$5,284
NZ$5,284
NZ$755 per night
includes taxes & fees
Image gallery for Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!
9.69.6 out of 10 rating
Exceptional
(283 reviews)
Summer Deals! OCEANFRONT Lux 1300sf with Stunning Views & All Amenities of home!
Key Largo, FL
8% off
Price is NZ$3,219
NZ$3,219
NZ$460 per night
includes taxes & fees
Image gallery for Kampground Escape w/ Kayaks, Heated Pool & Marina!
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Kampground Escape w/ Kayaks, Heated Pool & Marina!
Key Largo, FL
8% off
Price is NZ$2,894
NZ$2,894
NZ$413 per night
includes taxes & fees
Image gallery for Paradise Key Largo
9.89.8 out of 10 rating
Exceptional
(15 reviews)
Paradise Key Largo
Key Largo, FL
7% off
Price is NZ$3,350
NZ$3,350
NZ$479 per night
includes taxes & fees
Image gallery for Oceanview Luxe Retreat w/ Rooftop
1010 out of 10 rating
Exceptional
(53 reviews)
Oceanview Luxe Retreat w/ Rooftop
Key Largo, FL
7% off
Price is NZ$6,389
NZ$6,389
NZ$913 per night
includes taxes & fees
Image gallery for Delightful RV in Key Largo, FL
9.29.2 out of 10 rating
Wonderful
(14 reviews)
Delightful RV in Key Largo, FL
Key Largo, FL
8% off
Price is NZ$2,451
NZ$2,451
NZ$350 per night
includes taxes & fees
Image gallery for Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock
1010 out of 10 rating
Exceptional
(6 reviews)
Islamorada Keys Waterfront Heated Pool Hottub Luxury Canal Home w Private Dock
Tavernier, FL
8% off
Price is NZ$10,260
NZ$10,260
NZ$1,466 per night
includes taxes & fees
Image gallery for Key Largo home with new hot tub!
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Key Largo home with new hot tub!
Key Largo, FL
12% off
Price is NZ$6,421
NZ$6,421
NZ$917 per night
includes taxes & fees
Image gallery for NEWLY RENOVATED Oceanside Oasis at Kawama Tower
1010 out of 10 rating
Exceptional
(75 reviews)
NEWLY RENOVATED Oceanside Oasis at Kawama Tower
Key Largo, FL
8% off
Price is NZ$4,263
NZ$4,263
NZ$609 per night
includes taxes & fees
Image gallery for KEY LARGO WEEKLY PARADISE HOUSE RENTAL
1010 out of 10 rating
Exceptional
(13 reviews)
KEY LARGO WEEKLY PARADISE HOUSE RENTAL
Key Largo, FL
8% off
Price is NZ$7,766
NZ$7,766
NZ$1,109 per night
includes taxes & fees
Image gallery for Charming Home in Key Largo
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Charming Home in Key Largo
Key Largo, FL
15% off
Price is NZ$2,520
NZ$2,520
NZ$360 per night
includes taxes & fees
Image gallery for Stunning Morning View w/ Boat Slip, Cove
1010 out of 10 rating
Exceptional
(38 reviews)
Stunning Morning View w/ Boat Slip, Cove
Key Largo, FL
8% off
Price is NZ$3,420
NZ$3,420
NZ$489 per night
includes taxes & fees
Image gallery for Key Largo 'Shangri La' Experience
1010 out of 10 rating
Exceptional
(5 reviews)
Key Largo 'Shangri La' Experience
Key Largo, FL
8% off
Price is NZ$3,640
NZ$3,640
NZ$520 per night
includes taxes & fees
Image gallery for Tranquilo Paraiso [Ocean Pointe 2407]
9.89.8 out of 10 rating
Exceptional
(42 reviews)
Tranquilo Paraiso [Ocean Pointe 2407]
Tavernier, FL
7% off
Price is NZ$2,737
NZ$2,737
NZ$391 per night
includes taxes & fees
Image gallery for Paradise in Beautiful Key Largo!! Amazing Views!!
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Paradise in Beautiful Key Largo!! Amazing Views!!
Key Largo, FL
12% off
Price is NZ$4,605
NZ$4,605
NZ$658 per night
includes taxes & fees
Image gallery for NEW! OCEANSIDE CASA AZUL!VOTED #1! GOLF CART-PICKELBALL-KAYAK- BEACH- POOLS-FISH
9.89.8 out of 10 rating
Exceptional
(189 reviews)
NEW! OCEANSIDE CASA AZUL!VOTED #1! GOLF CART-PICKELBALL-KAYAK- BEACH- POOLS-FISH
Key Largo, FL
8% off
Price is NZ$5,915
NZ$5,915
NZ$845 per night
includes taxes & fees
Image gallery for Stay 2 nights, 3rd night 10% thru June 30th, 2025
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Stay 2 nights, 3rd night 10% thru June 30th, 2025
Key Largo, FL
14% off
Price is NZ$2,617
NZ$2,617
NZ$374 per night
includes taxes & fees
Image gallery for Stunning Views & Modern Comforts at Ocean Pointe 2215
1010 out of 10 rating
Exceptional
(57 reviews)
Stunning Views & Modern Comforts at Ocean Pointe 2215
Tavernier, FL
7% off
Price is NZ$3,131
NZ$3,131
NZ$447 per night
includes taxes & fees
Image gallery for Anglers Reef Islamorada
1010 out of 10 rating
Exceptional
(10 reviews)
Anglers Reef Islamorada
Islamorada, FL
7% off
Price is NZ$5,790
NZ$5,790
NZ$827 per night
includes taxes & fees
Image gallery for Enjoy this modern and cozy house in Key Largo Florida.
1010 out of 10 rating
Exceptional
(13 reviews)
Enjoy this modern and cozy house in Key Largo Florida.
Key Largo, FL
8% off
Price is NZ$4,496
NZ$4,496
NZ$642 per night
includes taxes & fees
Image gallery for NEW! OCEANSIDE CASA LARGO TROPICAL GETAWAY! PICKLEB-BEACH-POOL-KAYAK-TENNI-FISH
1010 out of 10 rating
Exceptional
(7 reviews)
NEW! OCEANSIDE CASA LARGO TROPICAL GETAWAY! PICKLEB-BEACH-POOL-KAYAK-TENNI-FISH
Key Largo, FL
8% off
Price is NZ$5,915
NZ$5,915
NZ$845 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Old Road Gallery
10 Million Dollar 2 Acre Bayside Beach Compound w Boat Dockage is One of A Kind
Sleeps 20 · 6 bedrooms · 6 bathrooms
1010 out of 10
Exceptionalexceptional
53 reviews(53 reviews)
Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC
Sleeps 5 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
35 reviews(35 reviews)
Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
179 reviews(179 reviews)
Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
217 reviews(217 reviews)
Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina & more....
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
261 reviews(261 reviews)
Aqua Lodge Houseboat "The Grey Lady"
Sleeps 6 · 4 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
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, gardens and more
More for lessMore space, more privacy, more amenities — more value