Holiday rentals near Old Road Gallery
We found 2,586 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:18 Jul - 25 Jul
Image gallery for Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

1010 out of 10 rating
Exceptional
(12 reviews)
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055
Islamorada, FL
8% off
Price is NZ$6,972
NZ$6,972
NZ$996 per night
includes taxes & fees
Image gallery for Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.

1010 out of 10 rating
Exceptional
(31 reviews)
Canal home in Islamorada. Views from 2nd fl pool, partial 65' of dock.
Tavernier, FL
7% off
Price is NZ$17,093
NZ$17,093
NZ$2,442 per night
includes taxes & fees
Image gallery for Delightful RV in Key Largo, FL

9.09.0 out of 10 rating
Wonderful
(12 reviews)
Delightful RV in Key Largo, FL
Key Largo, FL
8% off
Price is NZ$3,251
NZ$3,251
NZ$464 per night
includes taxes & fees
Image gallery for Key Largo Getaway with Bay View

1010 out of 10 rating
Exceptional
(21 reviews)
Key Largo Getaway with Bay View
Key Largo, FL
8% off
Price is NZ$3,172
NZ$3,172
NZ$453 per night
includes taxes & fees
Image gallery for Paradise in the Florida Keys at our Moon Bay Condo

1010 out of 10 rating
Exceptional
(17 reviews)
Paradise in the Florida Keys at our Moon Bay Condo
Key Largo, FL
8% off
Price is NZ$4,231
NZ$4,231
NZ$604 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
(6 reviews)
NEW! OCEANSIDE CASA LARGO TROPICAL GETAWAY! PICKLEB-BEACH-POOL-KAYAK-TENNI-FISH
Key Largo, FL
8% off
Price is NZ$8,050
NZ$8,050
NZ$1,150 per night
includes taxes & fees
Image gallery for Your Island Home Away From Home!

9.69.6 out of 10 rating
Exceptional
(58 reviews)
Your Island Home Away From Home!
Key Largo, FL
8% off
Price is NZ$5,621
NZ$5,621
NZ$803 per night
includes taxes & fees
Image gallery for Remodeled Key Largo Townhome in Kawama w/ Pools, Private Marina, Lagoon, Tennis

9.69.6 out of 10 rating
Exceptional
(45 reviews)
Remodeled Key Largo Townhome in Kawama w/ Pools, Private Marina, Lagoon, Tennis
Key Largo, FL
8% off
Price is NZ$6,769
NZ$6,769
NZ$967 per night
includes taxes & fees
Image gallery for Sugar Cane - Florida Keys tropical retreat. Newly renovated!

1010 out of 10 rating
Exceptional
(35 reviews)
Sugar Cane - Florida Keys tropical retreat. Newly renovated!
Tavernier, FL
8% off
Price is NZ$3,622
NZ$3,622
NZ$517 per night
includes taxes & fees
Image gallery for Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach

9.69.6 out of 10 rating
Exceptional
(9 reviews)
Bayfront Cottage Located on the Bay in Sunset Cove with Sandy Beach
Key Largo, FL
8% off
Price is NZ$3,285
NZ$3,285
NZ$469 per night
includes taxes & fees
Image gallery for Modern, comfortable and convenient condo with stunning views! Remodeled 12-2024

9.69.6 out of 10 rating
Exceptional
(121 reviews)
Modern, comfortable and convenient condo with stunning views! Remodeled 12-2024
Tavernier, FL
12% off
Price is NZ$3,917
NZ$3,917
NZ$560 per night
includes taxes & fees
Image gallery for Water Front Living - Gulf Paradise in Key Largo!

9.89.8 out of 10 rating
Exceptional
(58 reviews)
Water Front Living - Gulf Paradise in Key Largo!
Key Largo, FL
8% off
Price is NZ$2,886
NZ$2,886
NZ$412 per night
includes taxes & fees
Image gallery for Prívate suite in Calusa Campgrounds

9.29.2 out of 10 rating
Wonderful
(9 reviews)
Prívate suite in Calusa Campgrounds
Key Largo, FL
7% off
Price is NZ$2,217
NZ$2,217
NZ$317 per night
includes taxes & fees
Image gallery for Key largos's hidden gem

9.29.2 out of 10 rating
Wonderful
(12 reviews)
Key largos's hidden gem
Key Largo, FL
11% off
Price is NZ$2,599
NZ$2,599
NZ$371 per night
includes taxes & fees
Image gallery for Tropical Paradise at Moon Bay Key Largo, Florida

1010 out of 10 rating
Exceptional
(16 reviews)
Tropical Paradise at Moon Bay Key Largo, Florida
Key Largo, FL
8% off
Price is NZ$5,070
NZ$5,070
NZ$724 per night
includes taxes & fees
Image gallery for Amazing Key Largo Tropical Paradise 3/3 Townhouse with Water Lagoon view

9.49.4 out of 10 rating
Exceptional
(10 reviews)
Amazing Key Largo Tropical Paradise 3/3 Townhouse with Water Lagoon view
Key Largo, FL
8% off
Price is NZ$6,902
NZ$6,902
NZ$986 per night
includes taxes & fees
Image gallery for Kampground Escape w/ Kayaks, Heated Pool & Marina!

1010 out of 10 rating
Exceptional
(8 reviews)
Kampground Escape w/ Kayaks, Heated Pool & Marina!
Key Largo, FL
8% off
Price is NZ$2,970
NZ$2,970
NZ$424 per night
includes taxes & fees
Image gallery for Breathtaking Waterfront Key Largo Boat Slip, Oasis

1010 out of 10 rating
Exceptional
(19 reviews)
Breathtaking Waterfront Key Largo Boat Slip, Oasis
Key Largo, FL
8% off
Price is NZ$5,077
NZ$5,077
NZ$725 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
(186 reviews)
NEW! OCEANSIDE CASA AZUL!VOTED #1! GOLF CART-PICKELBALL-KAYAK- BEACH- POOLS-FISH
Key Largo, FL
8% off
Price is NZ$7,865
NZ$7,865
NZ$1,124 per night
includes taxes & fees
Image gallery for Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal

9.69.6 out of 10 rating
Exceptional
(53 reviews)
Venetian Tropics weekly Pvt home w/heated Pool, 3 bedroom /70ft dock w/canal
Islamorada, FL
8% off
Price is NZ$9,726
NZ$9,726
NZ$1,389 per night
includes taxes & fees
Image gallery for Waterfront Sunset View in the Aqua Villa Sand Dollar @ Mangrove Resort LLC

9.49.4 out of 10 rating
Exceptional
(34 reviews)
Waterfront Sunset View in the Aqua Villa Sand Dollar @ Mangrove Resort LLC
Tavernier, FL
8% off
Price is NZ$4,627
NZ$4,627
NZ$661 per night
includes taxes & fees
Image gallery for Paradise in Beautiful Key Largo!! Amazing Views!!

9.89.8 out of 10 rating
Exceptional
(21 reviews)
Paradise in Beautiful Key Largo!! Amazing Views!!
Key Largo, FL
12% off
Price is NZ$4,726
NZ$4,726
NZ$675 per night
includes taxes & fees
Image gallery for Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!

9.89.8 out of 10 rating
Exceptional
(58 reviews)
Re-energize at our spacious condo! Get 10% off stays of 7+ days. Book now!
Key Largo, FL
8% off
Price is NZ$4,201
NZ$4,201
NZ$600 per night
includes taxes & fees
Image gallery for COASTAL ELEGANCE FOR RENT IN ISLAMORADA !!! PARADISE FOUND ON DEEP WATER

9.89.8 out of 10 rating
Exceptional
(84 reviews)
COASTAL ELEGANCE FOR RENT IN ISLAMORADA !!! PARADISE FOUND ON DEEP WATER
Tavernier, FL
5% off
Price is NZ$8,841
NZ$8,841
NZ$1,263 per night
includes taxes & fees
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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
52 reviews(52 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
173 reviews(173 reviews)
Amazing Ocean view at Ocean Pointe w/Heated Pool
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
29 reviews(29 reviews)
Oceanfront Key Largo Paradise with Private Beach~Pool~Tennis~Marina & more....
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
251 reviews(251 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
208 reviews(208 reviews)
RESERVE QUICKLY! YOU’LL LOVE IT! EVERYONE DOES!
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
177 reviews(177 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