
Holiday rentals near Old Cutler Trail
We found 10,206 holiday rentals — enter your dates for availability
Find the perfect holiday home within close proximity to Old Cutler Trail. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as parking and a TV. Whatever you're looking for, you'll be able to choose a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Old Cutler Trail
Showing deals for:7 Nov - 14 Nov
Image gallery for Villa heated-Luxury Oasis: Pool, Cabanas & Court

8.68.6 out of 10 rating
Excellent
(9 reviews)
Villa heated-Luxury Oasis: Pool, Cabanas & Court
Cutler Bay, FL
8% off
Price is £5,284
£5,284
£755 per night
includes taxes & fees
Image gallery for South Miami House with Pool & Backyard Oasis, BBQ Grill, 5 Bd, fits 11 guests

9.89.8 out of 10 rating
Exceptional
(13 reviews)
South Miami House with Pool & Backyard Oasis, BBQ Grill, 5 Bd, fits 11 guests
Miami, FL
20% off
Price is £3,675
£3,675
£525 per night
includes taxes & fees
Image gallery for New Listing!! Charming 2/2 cottage in wonderful Homestead with AC, WiFi

1010 out of 10 rating
Exceptional
(25 reviews)
New Listing!! Charming 2/2 cottage in wonderful Homestead with AC, WiFi
Homestead, FL
7% off
Price is £1,047
£1,047
£150 per night
includes taxes & fees
Image gallery for Villa w/a Huge Terrace w/Arg Grill+Mini Golf+Billiards & Heated Pool!

9.09.0 out of 10 rating
Wonderful
(19 reviews)
Villa w/a Huge Terrace w/Arg Grill+Mini Golf+Billiards & Heated Pool!
North Miami Beach, Florida
9% off
Price is £3,372
£3,372
£482 per night
includes taxes & fees
Image gallery for House - Miami pool house, near Miami Int Airport and attractions.

9.09.0 out of 10 rating
Wonderful
(20 reviews)
House - Miami pool house, near Miami Int Airport and attractions.
Miami Springs, FL
7% off
Price is £2,359
£2,359
£337 per night
includes taxes & fees
Image gallery for Family Friendly Kendall Retreat w/ Pool

9.69.6 out of 10 rating
Exceptional
(28 reviews)
Family Friendly Kendall Retreat w/ Pool
Miami, FL
8% off
Price is £2,178
£2,178
£311 per night
includes taxes & fees
Image gallery for Spacious and Modern Home

8.08.0 out of 10 rating
Very good
(12 reviews)
Spacious and Modern Home
Miami Gardens, FL
8% off
Price is £1,930
£1,930
£276 per night
includes taxes & fees
Image gallery for 4BR/3BA Miami Welcoming Waterfront Wonder w/ Pool!

9.69.6 out of 10 rating
Exceptional
(13 reviews)
4BR/3BA Miami Welcoming Waterfront Wonder w/ Pool!
North Miami Beach, FL
8% off
Price is £4,569
£4,569
£653 per night
includes taxes & fees
Image gallery for Miami Tropical Retreat - Villa Tropical

1010 out of 10 rating
Exceptional
(33 reviews)
Miami Tropical Retreat - Villa Tropical
North Miami, FL
11% off
Price is £2,750
£2,750
£393 per night
includes taxes & fees
Image gallery for North Miami Beach family villa with HEATED pool & grill. Minutes to beach!

9.09.0 out of 10 rating
Wonderful
(68 reviews)
North Miami Beach family villa with HEATED pool & grill. Minutes to beach!
North Miami Beach, FL
8% off
Price is £3,115
£3,115
£445 per night
includes taxes & fees
Image gallery for Miami Beach ocean front ocean view resort 2-2 (Alexander Beach Resort)

8.88.8 out of 10 rating
Excellent
(31 reviews)
Miami Beach ocean front ocean view resort 2-2 (Alexander Beach Resort)
Miami Beach, FL
7% off
Price is £1,878
£1,878
£268 per night
includes taxes & fees
Image gallery for Private Garden-Pool Oasis

1010 out of 10 rating
Exceptional
(15 reviews)
Private Garden-Pool Oasis
Miami, FL
16% off
Price is £2,009
£2,009
£287 per night
includes taxes & fees
Image gallery for This spacious and beautiful farm house, to be in touch with nature.

9.89.8 out of 10 rating
Exceptional
(19 reviews)
This spacious and beautiful farm house, to be in touch with nature.
Miami (and vicinity), FL
11% off
Price is £2,100
£2,100
£300 per night
includes taxes & fees
Image gallery for Private Apartment Miami Kendall near Zoo, The Falls Mall, and Miami Dade College

8.88.8 out of 10 rating
Excellent
(24 reviews)
Private Apartment Miami Kendall near Zoo, The Falls Mall, and Miami Dade College
Miami, FL
7% off
Price is £590
£590
£84 per night
includes taxes & fees
Image gallery for South Miami Oasis with lake views! Short drive to beach!

9.89.8 out of 10 rating
Exceptional
(22 reviews)
South Miami Oasis with lake views! Short drive to beach!
Miami, FL
10% off
Price is £1,557
£1,557
£222 per night
includes taxes & fees
Image gallery for We are centrally located. 5 mins from MIA airport 10-15 mins from Port of Miami!

9.69.6 out of 10 rating
Exceptional
(33 reviews)
We are centrally located. 5 mins from MIA airport 10-15 mins from Port of Miami!
Miami, FL
7% off
Price is £1,212
£1,212
£173 per night
includes taxes & fees
Image gallery for Sorrento @Fontainebleau Oceanview Double Wide Balcony Full Kitchen. Washer/Dryer

9.89.8 out of 10 rating
Exceptional
(73 reviews)
Sorrento @Fontainebleau Oceanview Double Wide Balcony Full Kitchen. Washer/Dryer
Miami Beach, FL
12% off
Price is £3,082
£3,082
£440 per night
includes taxes & fees
Image gallery for Tropical Miami/Heated pool/Basketball Court/Pin Pong Table/Patio Chess/Mini Golf

9.69.6 out of 10 rating
Exceptional
(19 reviews)
Tropical Miami/Heated pool/Basketball Court/Pin Pong Table/Patio Chess/Mini Golf
Miami, FL
8% off
Price is £3,141
£3,141
£449 per night
includes taxes & fees
Image gallery for Castle M16 Ocean/Pool view, balcony, gym. tennis, & free valet parking!

8.08.0 out of 10 rating
Very good
(67 reviews)
Castle M16 Ocean/Pool view, balcony, gym. tennis, & free valet parking!
Miami Beach, FL
7% off
Price is £3,282
£3,282
£469 per night
includes taxes & fees
Image gallery for Luxury Villa w/ Mini Golf+Huge Fire Pit+Billiards & Heated Pool

8.48.4 out of 10 rating
Very good
(21 reviews)
Luxury Villa w/ Mini Golf+Huge Fire Pit+Billiards & Heated Pool
Ojus, Florida
9% off
Price is £3,605
£3,605
£515 per night
includes taxes & fees
Image gallery for Exquisite Oceanfront Condo In Resort

9.89.8 out of 10 rating
Exceptional
(61 reviews)
Exquisite Oceanfront Condo In Resort
Miami Beach, FL
7% off
Price is £2,388
£2,388
£341 per night
includes taxes & fees
Image gallery for Ocean view corner suite. full kitchen, washer & dryer, 2 full bathrooms

9.69.6 out of 10 rating
Exceptional
(100 reviews)
Ocean view corner suite. full kitchen, washer & dryer, 2 full bathrooms
Miami Beach, FL
12% off
Price is £2,801
£2,801
£400 per night
includes taxes & fees
Image gallery for Four Seasons Brickell, King Bed with city and partial ocean view

9.89.8 out of 10 rating
Exceptional
(11 reviews)
Four Seasons Brickell, King Bed with city and partial ocean view
Miami, FL
8% off
Price is £1,921
£1,921
£274 per night
includes taxes & fees
Image gallery for dream space to relax in miami

9.69.6 out of 10 rating
Exceptional
(50 reviews)
dream space to relax in miami
Miami, FL
7% off
Price is £550
£550
£79 per night
includes taxes & fees
Find spaces that suit your style
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Find properties near top attractions in Old Cutler Trail
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Find the best place to stay - Old Cutler Trail
Miami Luxe: 5BR Retreat w/ Pool & Golf Views
Sleeps 12 · 5 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
Beautiful 5-bedroom house in enchanting Cutler Bay, Private: Pool, Jacuzzi, Gym
Sleeps 14 · 5 bedrooms · 4 bathrooms
Family Retreat: Pool, Games & Private Apartment
Sleeps 12 · 4 bedrooms · 4 bathrooms
Spacious Fun House w/ Games & Heated Pool
Sleeps 16 · 6 bedrooms · 4 bathrooms
Prime Location + Pool + Sleeps 10 --> Luxe Miami Oasis Home
Sleeps 11 · 4 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Villa Miami Oasis in the Sun
Sleeps 12 · 4 bedrooms · 3 bathrooms
Top rated rentals - Old Cutler Trail
Very good
1010 out of 10
Exceptionalexceptional
25 reviews(25 reviews)
Nice, clean and tidy property, lovely quiet area which is out of the way but just what we wanted. Hosts were really nice and very helpful. Wish we could have stayed longer.
Tonya R.
Stayed Jul 2025
50th birthday celebration
1010 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
I’ve just spent an amazing 5 days at Sandcastle villa in Miami with ten friends from London for my 50th birthday celebration.The pictures do not do the property justice. It had everything you could wish for to make it a special stay.The owner John was incredibly helpful and friendly. Nothing was so much trouble for him. If you’re looking for somewhere to have a memorable stay, then this is the place for you
Benjamin A.
Stayed Apr 2025
75 year old group
1010 out of 10
Exceptionalexceptional
143 reviews(143 reviews)
Awesome in all regards including the property manager
Kit C.
Stayed Nov 2024
It was disaster!
1010 out of 10
Exceptionalexceptional
77 reviews(77 reviews)
The dirtiest place i ever saw!
I have all the pictures with me, i wish i could be able to put here.
I left the apartment first day we couldnt able to sleep it was terrible.
They are so unhelpfull. Even you are not taking the key of the house from residence lobby, they were completely weirdest people . I hate it!
I will never rent a place from them!
Ipek A.
Stayed Jan 2024
Superb beachfront Miami apartment - June 2023
1010 out of 10
Exceptionalexceptional
306 reviews(306 reviews)
Can’t believe we actually made it - originally booked for 2020 pre-Covid, Mickael was happy to honour 2020 rates even though dates changed several times, he was happy to accommodate us & kept in touch all the time. Check in with Elana was simple, apartment was spotless & as described with high end furnishings & gadgets. Good central location for exploring Miami. Beachfront location. Highly recommended.
Neil & Sharon P.
Stayed Jun 2023
Miami Home
1010 out of 10
Exceptionalexceptional
101 reviews(101 reviews)
We stayed in this lovely, cosy home for 4 weeks and felt very safe taking some evening walks around the neighbourhood. We enjoyed relaxing on all the comfortable furniture by the private pool and BBQ. Our host was very welcoming and always quick to answer any questions and give advise about the area. We would love to stay again.
Marion H.
Stayed Sept 2022
Amazing Host
1010 out of 10
Exceptionalexceptional
117 reviews(117 reviews)
This is the second time we have stayed at Kevin's condo at the St Regis. The condo, room and service was terrific. The location across from Bal Harbor shops is superb.
Rashmi N.
Stayed Apr 2022
- 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, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value