1+ Vacation Rentals Near Midtown |
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Castle In Hawaii - Vacation Rentals in Midtown

Atlantis House Palm Suite, close to beach, off street parking, renovated From US $521
         

9.6 (4 Reviews)
Villa
Atlantis House Palm Suite, close to beach, off street parking, renovated
  • Security/Safety
  • Child Friendly

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Luxury Places to Stay in Midtown

Over 86+ Luxury Places to Stay in or Near Midtown
Belle of the Beach by Last Key Realty From US $2,390
         

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New
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Belle of the Beach by Last Key Realty
  • Parking
  • Pet Friendly
  • Pool

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*BELLE OF THE BEACH @ CASA EAST* Beach House + LAST KEY SERVICES… From US $2,385
         

10.0 (63 Reviews)
House
*BELLE OF THE BEACH @ CASA EAST* Beach House + LAST KEY SERVICES…
  • Air Conditioner
  • Parking
  • Pet Friendly

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New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis From US $1,647
         

6.0 (1 Review)
House
New 4BR/4BA Sleeps 12+ minutes to Beach & Duval St. Private backyard pool oasis
  • Air Conditioner
  • Parking
  • Pet Friendly

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Villa Paradiso: A unique mid-town paradise From US $1,610
         

9.8 (175 Reviews)
House
Villa Paradiso: A unique mid-town paradise
  • Air Conditioner
  • Parking
  • Pet Friendly

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Panoramic 3BR/3BA Condo - Direct Beach Ocean Front From US $1,101
         

10.0 (125 Reviews)
Condo
Panoramic 3BR/3BA Condo - Direct Beach Ocean Front
  • Air Conditioner
  • Parking
  • Pool

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A Bella Capri in Key West by the Beach! *Monthly rental* From US $967
         

9.2 (5 Reviews)
House
A Bella Capri in Key West by the Beach! *Monthly rental*
  • Air Conditioner
  • Parking
  • Pool

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Three Bedroom, 3 Bath pool home close to the Atlantic! From US $915
         

New
House
Three Bedroom, 3 Bath pool home close to the Atlantic!
  • Air Conditioner
  • Parking
  • Pool

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~BLUE HAVEN~ Welcome to this single-story retreat with a pool! From US $846
         

10.0 (1 Review)
House
~BLUE HAVEN~ Welcome to this single-story retreat with a pool!
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Midtown

Over 51+ Top-Rated Vacation Rentals with a Pool in or Near Midtown
*LARGE PRIVATE HEATED POOL and PATIO*1/3 Mile from Beach From US $213
         

10.0 (19 Reviews)
House
*LARGE PRIVATE HEATED POOL and PATIO*1/3 Mile from Beach
  • Air Conditioner
  • Parking
  • Pet Friendly

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BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage From US $486
         

10.0 (8 Reviews)
House
BE STILL- 4 Bedroom, 3 Bath with POOL & Guest Cottage
  • Air Conditioner
  • Parking
  • Pool

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Gorgeous beach bungalow just steps from the beach! From US $419
         

10.0 (6 Reviews)
House
Gorgeous beach bungalow just steps from the beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

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SOUTHERNMOST SWIM AND SOCIAL CLUB From US $432
         

10.0 (4 Reviews)
House
SOUTHERNMOST SWIM AND SOCIAL CLUB
  • Air Conditioner
  • Parking
  • Pet Friendly

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Orchid Oasis - Only Minutes from Smather's and Rest Beaches! From US $720
         

10.0 (3 Reviews)
House
Orchid Oasis - Only Minutes from Smather's and Rest Beaches!
  • Air Conditioner
  • Parking
  • Pool

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HEART AND SOUL ~ Sophisticated 5 BR/Near Beach/Perfect Fireworks Spot! From US $689
         

10.0 (2 Reviews)
House
HEART AND SOUL ~ Sophisticated 5 BR/Near Beach/Perfect Fireworks Spot!
  • Air Conditioner
  • Parking
  • Pet Friendly

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*THE ENCHANTED ROSE @ BEACHSIDE* Gorgeous Home & Pool + LAST KEY SERVICES… From US $430
         

10.0 (2 Reviews)
House
*THE ENCHANTED ROSE @ BEACHSIDE* Gorgeous Home & Pool + LAST KEY SERVICES…
  • Air Conditioner
  • Parking
  • Pet Friendly

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FLAMINGO ROSE ~ Midtown 3 Bedroom, 2 Bathroom Home w/Pool & Parking! From US $405
         

10.0 (2 Reviews)
House
FLAMINGO ROSE ~ Midtown 3 Bedroom, 2 Bathroom Home w/Pool & Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet-Friendly Vacation Rentals in Midtown

Over 26+ Pet-Friendly Vacation Rentals in or Near Midtown
Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House From US $708
         

10.0 (1 Review)
House
Eliza's Secret - Elegant Tropical Oasis with Private Pool & Guest House
  • Air Conditioner
  • Pet Friendly
  • Pool

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POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching! From US $660
         

10.0 (1 Review)
House
POCKETFUL OF SUNSHINE ~ 5 BR Near Beach and Prime Fireworks Watching!
  • Air Conditioner
  • Parking
  • Pet Friendly

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BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/Pool! From US $527
         

10.0 (1 Review)
House
BANYAN ROSE ~ Renovated 4 Bedroom, 2 Bathroom Midtown Home w/Pool!
  • Air Conditioner
  • Parking
  • Pet Friendly

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WALKING ON SUNSHINE ~ Exquisite 3 BR, 3 Ba Home w/Heated Pool & Parking! From US $404
         

9.6 (4 Reviews)
House
WALKING ON SUNSHINE ~ Exquisite 3 BR, 3 Ba Home w/Heated Pool & Parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Atlantis House Main Residence From US $369
         

9.0 (2 Reviews)
House
Atlantis House Main Residence
  • Air Conditioner
  • Pet Friendly
  • TV

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Southernmost Serenity - 3 Bedroom/2.5 Bathroom With Pool & Outdoor Bar From US $610
         

New
House
Southernmost Serenity - 3 Bedroom/2.5 Bathroom With Pool & Outdoor Bar
  • Air Conditioner
  • Parking
  • Pet Friendly

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*73 PALMS @ MIDTOWN* Renovated Home & Pool + LAST KEY SERVICES… From US $579
         

New
House
*73 PALMS @ MIDTOWN* Renovated Home & Pool + LAST KEY SERVICES…
  • Air Conditioner
  • Parking
  • Pet Friendly

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*BEAUTY OF THE BEACH* Monthly Beach House Rental + LAST KEY SERVICES… From US $576
         

New
House
*BEAUTY OF THE BEACH* Monthly Beach House Rental + LAST KEY SERVICES…
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Midtown

Over 7+ Large Vacation Homes & Villas in or Near Midtown
Island Time on Washington : Stylish 4BR Key West Home, Heated Pool, Dogs OK, Parking & Near Beaches
New
From US $534
         

New
House
Island Time on Washington : Stylish 4BR Key West Home, Heated Pool, Dogs OK, Parking & Near Beaches
  • Air Conditioner
  • Pet Friendly
  • Pool

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Casa del Sol From US $468
         

New
House
Casa del Sol
  • Air Conditioner
  • Pet Friendly
  • TV

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Private Resort Oasis From US $982
         

10.0 (40 Reviews)
House
Private Resort Oasis
  • Air Conditioner
  • Parking
  • Pool

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Palms and Pool Paradise From US $547
         

10.0 (1 Review)
House
Palms and Pool Paradise
  • Air Conditioner
  • Parking
  • Pet Friendly

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**VILLA MODERNA @ MIDTOWN** Immaculate Home & Pool + LAST KEY SERVICES… From US $325
         

10.0 (1 Review)
House
**VILLA MODERNA @ MIDTOWN** Immaculate Home & Pool + LAST KEY SERVICES…
  • Air Conditioner
  • Pet Friendly
  • Pool

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Sea Glass Cottage Key West,FL From US $264
         

New
House
Sea Glass Cottage Key West,FL
  • Air Conditioner
  • Bedding/Linens
  • Child Friendly

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**SOL VERDÉ @ BEACHSIDE** Beach House & Pool + LAST KEY SERVICES… From US $230
         

New
House
**SOL VERDÉ @ BEACHSIDE** Beach House & Pool + LAST KEY SERVICES…
  • Air Conditioner
  • Pool
  • Wheelchair Accessible

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Wheelchair Accessible Vacation Homes in Midtown

Over 4+ Wheelchair Accessible Vacation Homes in or Near Midtown
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym From US $546
         

9.8 (302 Reviews)
Condo
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
  • Air Conditioner
  • Parking
  • Pool

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Flagler Station From US $408
         

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New
House
Flagler Station
  • Air Conditioner
  • Pool
  • Wheelchair Accessible

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Top floor amazing view Toms Chicken Coop awaits your next stay. Best value From US $691
         

9.8 (153 Reviews)
Condo
Top floor amazing view Toms Chicken Coop awaits your next stay. Best value
  • Air Conditioner
  • Parking
  • Pool

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Poolside Palms Paradise From US $275
         

5.0 (1 Review)
House
Poolside Palms Paradise
  • Air Conditioner
  • Pet Friendly
  • Pool

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Midtown Varoom and Airbnb Places to Stay Under $200

Over 1+ Midtown Varoom and Airbnb Places to Stay Under $200
Under The Palms by AvantStay | Private Pool | Outdoor Dining | Close to Beach From US $197
         

New
House
Under The Palms by AvantStay | Private Pool | Outdoor Dining | Close to Beach
  • Air Conditioner
  • Pet Friendly
  • Pool

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Instantly Bookable Vacation Homes in Midtown

Over 30+ Instantly Bookable Vacation Homes in or Near Midtown
Atlantis House Suites From US $793
         

10.0 (2 Reviews)
House
Atlantis House Suites
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Honeymoon Palm Suite near Higgs Beach From US $699
         

10.0 (2 Reviews)
Apartment
Honeymoon Palm Suite near Higgs Beach
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Honeymoon Banyan Suite near Higgs Beach From US $470
         

10.0 (2 Reviews)
Apartment
Honeymoon Banyan Suite near Higgs Beach
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Tranquil Retreat by the Beach-4 bedroom 3 bath home w/private pool, parking From US $295
         

8.0 (1 Review)
House
Tranquil Retreat by the Beach-4 bedroom 3 bath home w/private pool, parking
  • Air Conditioner
  • Parking
  • Pool

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Sumptuous Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer From US $366
         

7.8 (7 Reviews)
House
Sumptuous Home with Private Pool, Central AC, WiFi, and Private Washer/Dryer
  • Air Conditioner
  • Parking
  • Pool

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BE AS YOU ARE - 3 Bedroom/3 Bathroom - Mid Town KEY WEST w/POOL From US $607
         

New
House
BE AS YOU ARE - 3 Bedroom/3 Bathroom - Mid Town KEY WEST w/POOL
  • Air Conditioner
  • Parking
  • Pool

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POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/Pool! From US $573
         

New
House
POOLSIDE PARADISE ~ Charming 3 BR/2Ba Home w/Pool!
  • Air Conditioner
  • Parking
  • Pool

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Serendipity South: Premium Key West Pool Oasis Near The Beach From US $468
         

New
House
Serendipity South: Premium Key West Pool Oasis Near The Beach
  • Air Conditioner
  • Parking
  • Pool

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About Midtown Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Castleinhawaii Midtown, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Midtown. Places to stay near Midtown are 650 ft² on average, with prices averaging $521 a night.

Castleinhawaii makes it easy and safe to find and compare vacation rentals in Midtown with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Midtown

Type Count
Villas 1

Use these Quick Filters to Find a Vacation Rental in Midtown

★ Pro Tip: Castleinhawaii makes it easy to compare the best listings on Castleinhawaii homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Castleinhawaii homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Midtown.

Weather in Midtown

View the weather forecast for Midtown before booking your Midtown Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Complexes around Midtown, FL


Paradiso Paradise 1 Properties