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Cruise Vacations - Vacation Rentals in Meadows

The Crystalmarine Suite – Rustic Luxury on the Sea From US $506
         

10.0 (3 Reviews)
Boat Rental
The Crystalmarine Suite – Rustic Luxury on the Sea
  • Air Conditioner
  • Parking
  • TV

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Luxury Places to Stay in Meadows

Over 137+ Luxury Places to Stay in or Near Meadows
Bayview North One From US $2,792
         

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New
House
Bayview North One
  • Parking
  • Pool
  • Wheelchair Accessible

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Captains Daughter From US $2,560
         

New
House
Captains Daughter
  • Parking
  • Pet Friendly
  • View

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Meadows Manor From US $2,500
         

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New
House
Meadows Manor
  • Pool
  • Security/Safety
  • Child Friendly

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Meadows Manor | Elegant Oasis with Private Pool & Parking! From US $2,099
         

9.2 (11 Reviews)
House
Meadows Manor | Elegant Oasis with Private Pool & Parking!
  • Air Conditioner
  • Parking
  • Pool

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Bayview Retreat From US $2,086
         

New
House
Bayview Retreat
  • Parking
  • Pet Friendly
  • View

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SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage! From US $2,001
         

10.0 (1 Review)
House
SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Oversized home for the whole family w/private pool & dock From US $1,995
         

9.8 (138 Reviews)
House
Oversized home for the whole family w/private pool & dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL From US $1,958
         

10.0 (114 Reviews)
House
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Meadows

Over 116+ Top-Rated Vacation Rentals with a Pool in or Near Meadows
Old Town "Eleuthera" 2BR Waterfront Corner Condo From US $430
         

10.0 (28 Reviews)
Condo
Old Town "Eleuthera" 2BR Waterfront Corner Condo
  • Air Conditioner
  • Parking
  • Pet Friendly

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Curaçao Key West 2BR Condo w/Pool&Waterfront Dock From US $431
         

10.0 (24 Reviews)
Condo
Curaçao Key West 2BR Condo w/Pool&Waterfront Dock
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Palms -3 bedroom 2 bath home in The Meadows w/pool oasis & guest cottage From US $322
         

10.0 (20 Reviews)
House
The Palms -3 bedroom 2 bath home in The Meadows w/pool oasis & guest cottage
  • Air Conditioner
  • Parking
  • Pool

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Key West Andros 2BR Waterfront, Pool, Dock&Pet OK From US $861
         

10.0 (16 Reviews)
Condo
Key West Andros 2BR Waterfront, Pool, Dock&Pet OK
  • Air Conditioner
  • Parking
  • Pet Friendly

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Welcome to the Shady Palms - Private Pool - RealKeyWest From US $580
         

10.0 (6 Reviews)
House
Welcome to the Shady Palms - Private Pool - RealKeyWest
  • Air Conditioner
  • Parking
  • Pet Friendly

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Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi From US $292
         

10.0 (6 Reviews)
House
Fabulous Home with Private Saltwater Pool, Central AC, & High-Speed WiFi
  • Air Conditioner
  • Pool
  • TV

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PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool! From US $432
         

10.0 (4 Reviews)
House
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!
  • Air Conditioner
  • Parking
  • Pet Friendly

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"Dominica" Key West 2BR Dock, Pool, Pet-Friendly From US $432
         

10.0 (2 Reviews)
Condo
"Dominica" Key West 2BR Dock, Pool, Pet-Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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Pet-Friendly Vacation Rentals in Meadows

Over 52+ Pet-Friendly Vacation Rentals in or Near Meadows
Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly From US $610
         

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9.6 (14 Reviews)
House
Aruba - Downtown Waterfront 2x2 Dock & Pool Pet-Friendly
  • Air Conditioner
  • Parking
  • Pet Friendly

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ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows! From US $188
         

10.0 (1 Review)
House
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
  • Air Conditioner
  • Pet Friendly
  • TV

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~ CASABLANCA ~ Fabulous home w/private pool/parking, in a quiet location. From US $874
         

9.8 (119 Reviews)
House
~ CASABLANCA ~ Fabulous home w/private pool/parking, in a quiet location.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Florida | Waterfront 2BR/2BA w/Pool + Dock Access From US $650
         

9.8 (38 Reviews)
Condo
Florida | Waterfront 2BR/2BA w/Pool + Dock Access
  • Air Conditioner
  • Parking
  • Pet Friendly

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Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews From US $408
         

9.8 (15 Reviews)
House
Historic House, Gorgeous Porch, Great Location, See 5 Star Reviews
  • Air Conditioner
  • Parking
  • Pet Friendly

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~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking! From US $1,255
         

9.8 (9 Reviews)
House
~ CASABLANCA GRANDE ~ Old Town quiet duplex with pool, hot tub, and parking!
  • Air Conditioner
  • Parking
  • Pet Friendly

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SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/Pool! From US $757
         

9.8 (9 Reviews)
House
SECOND WIND ~ Charming 2 Bedroom, 2 Bathroom Home w/Pool!
  • Air Conditioner
  • Parking
  • Pet Friendly

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~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location. From US $685
         

9.6 (116 Reviews)
House
~ CASABLANCA TOO ~Chicly updated home with hot tub in a quiet location.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Meadows

Over 19+ Large Vacation Homes & Villas in or Near Meadows
St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet From US $1,672
         

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9.6 (7 Reviews)
House
St Croix - Downtown 4x4 Waterfront Penthouse Pool Dock Pet
  • Air Conditioner
  • Parking
  • Pet Friendly

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3-Story spacious conch style home w/private pool & dock! From US $1,521
         

9.8 (135 Reviews)
House
3-Story spacious conch style home w/private pool & dock!
  • Air Conditioner
  • Parking
  • Pool

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*MODERN IN THE MEADOWS @ THE MEADOWS* Chic Private Home & Pool + LAST KEY SERV From US $965
         

New
House
*MODERN IN THE MEADOWS @ THE MEADOWS* Chic Private Home & Pool + LAST KEY SERV
  • Air Conditioner
  • Parking
  • Pet Friendly

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BELLE MAISON ~ 5 BR/3 Ba Home w/Pool/Spa in The Meadows! From US $752
         

New
House
BELLE MAISON ~ 5 BR/3 Ba Home w/Pool/Spa in The Meadows!
  • Air Conditioner
  • Pet Friendly
  • Pool

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Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool From US $632
         

New
House
Luxury Mansion in Old Town Key West – Four Bedrooms, Private Pool
  • Air Conditioner
  • Parking
  • Pool

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Downtown Penthouse Waterviews Pool, Dock, Parking From US $1,400
         

9.6 (37 Reviews)
Condo
Downtown Penthouse Waterviews Pool, Dock, Parking
  • Air Conditioner
  • Parking
  • Pet Friendly

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St. Johns Waterfront 4BR Penthouse Pool Dock Park From US $1,354
         

9.6 (29 Reviews)
Condo
St. Johns Waterfront 4BR Penthouse Pool Dock Park
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront "St. Croix" Penthouse, Pool, Dock, Pet From US $1,460
         

9.6 (25 Reviews)
Condo
Waterfront "St. Croix" Penthouse, Pool, Dock, Pet
  • Air Conditioner
  • Parking
  • Pet Friendly

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Wheelchair Accessible Vacation Homes in Meadows

Over 16+ Wheelchair Accessible Vacation Homes in or Near Meadows
Bermuda Retreat-waterfront 2BR 2BA condo w/pool & boat slip From US $836
         

9.0 (96 Reviews)
Condo
Bermuda Retreat-waterfront 2BR 2BA condo w/pool & boat slip
  • Air Conditioner
  • Parking
  • Pool

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4-Bed, 4.5 Bath Condo & Bayfront Suites - NO CLEANING FEE (Non-Waterfront) From US $1,387
         

9.8 (124 Reviews)
Condo
4-Bed, 4.5 Bath Condo & Bayfront Suites - NO CLEANING FEE (Non-Waterfront)
  • Air Conditioner
  • Parking
  • Pool

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Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites & Marina - NO CLEANING FEE From US $1,249
         

9.8 (72 Reviews)
Condo
Waterfront 4 Bed, 4-Bath Condo @ Bayfront Suites & Marina - NO CLEANING FEE
  • Air Conditioner
  • Parking
  • Pool

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Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites & Marina - NO CLEANING FEE From US $1,279
         

9.8 (58 Reviews)
Condo
Waterfront 4-Bed 3-Bath Condo @ Bayfront Suites & Marina - NO CLEANING FEE
  • Air Conditioner
  • Parking
  • Pool

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Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE From US $1,366
         

9.6 (95 Reviews)
Condo
Waterfront 4-Bed, 4-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
  • Air Conditioner
  • Parking
  • Pool

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4-Bed 4.5 Bath Condo @ Bayfront Suites - NO CLEANING FEE (Non-Waterfront) From US $1,258
         

9.6 (95 Reviews)
Condo
4-Bed 4.5 Bath Condo @ Bayfront Suites - NO CLEANING FEE (Non-Waterfront)
  • Air Conditioner
  • Parking
  • Pool

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Waterfront 3-Bedroom Condo at Bayfront Suites & Marina - NO CLEANING FEE From US $1,231
         

9.6 (91 Reviews)
Condo
Waterfront 3-Bedroom Condo at Bayfront Suites & Marina - NO CLEANING FEE
  • Air Conditioner
  • Parking
  • Pool

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3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE From US $1,001
         

9.6 (78 Reviews)
Condo
3-Bedroom 3-Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
  • Air Conditioner
  • Parking
  • Pool

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Meadows Varoom and Airbnb Places to Stay Under $200

Over 9+ Meadows Varoom and Airbnb Places to Stay Under $200
Keys Please From US $169
         

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New
House
Keys Please
  • Air Conditioner
  • Pool
  • Balcony/Terrace

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NEWTON'S NEST ~ Adult Only, 1 Bedroom, 1 Bath Condo w/Shared Pool! From US $185
         

10.0 (1 Review)
Condo
NEWTON'S NEST ~ Adult Only, 1 Bedroom, 1 Bath Condo w/Shared Pool!
  • Air Conditioner
  • Pool
  • TV

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Authors of Key West Guest House From US $123
         

|
9.0 (1015 Reviews)
Bed & Breakfast
Authors of Key West Guest House
  • Air Conditioner
  • Pool
  • TV

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CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool! From US $178
         

8.8 (3 Reviews)
Condo
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
  • Air Conditioner
  • Pet Friendly
  • Pool

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The Palms Hotel From US $169
         

|
8.8 (1015 Reviews)
House
The Palms Hotel
  • Air Conditioner
  • Parking
  • Pool

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The Fleming Suite | 1 bed, 1 bath condo w/shared pool From US $189
         

6.0 (2 Reviews)
Condo
The Fleming Suite | 1 bed, 1 bath condo w/shared pool
  • Air Conditioner
  • Parking
  • Pool

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Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool From US $165
         

9.2 (131 Reviews)
Condo
Tropical Escape with Central Locale, Private Hot Tub, WiFi, and Shared Pool
  • Air Conditioner
  • Pool
  • TV

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PATHWAY TO PARADISE ~ 2 BR/2.5 Ba Townhome w/Shared Pool! From US $196
         

New
House
PATHWAY TO PARADISE ~ 2 BR/2.5 Ba Townhome w/Shared Pool!
  • Air Conditioner
  • Pool
  • TV

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Instantly Bookable Vacation Homes in Meadows

Over 40+ Instantly Bookable Vacation Homes in or Near Meadows
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Heated/Chilled Pool! From US $405
         

10.0 (1 Review)
House
The Conch Chateau: Stylishly Renovated Conch House in the Heart of Key West, Heated/Chilled Pool!
  • Air Conditioner
  • Pool
  • TV

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TRANQUILITY - Meadows Monthly Rental - Private Pool - 3BDR/3BA - RealKeyWest From US $584
         

9.8 (6 Reviews)
Cottage
TRANQUILITY - Meadows Monthly Rental - Private Pool - 3BDR/3BA - RealKeyWest
  • Air Conditioner
  • Pool
  • TV

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2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE From US $539
         

9.6 (61 Reviews)
Condo
2 Bedroom 1 Bath Condo at Bayfront Suites & Marina - NO CLEANING FEE
  • Air Conditioner
  • Parking
  • Pool

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Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches From US $558
         

9.6 (7 Reviews)
Condo
Palm Isle: Tropical 2nd-Floor Unit, Shared Heated Pool, Near Duval St, Historic Seaport & Beaches
  • Air Conditioner
  • Pool
  • TV

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Casa de Rosalie by AvantStay | Great Location w/Pool, BBQ & Outdoor Dining From US $403
         

9.6 (4 Reviews)
House
Casa de Rosalie by AvantStay | Great Location w/Pool, BBQ & Outdoor Dining
  • Air Conditioner
  • Parking
  • Pet Friendly

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Antigua Retreat- 2BR 2BA waterfront condo w/pool & boat slip From US $920
         

9.4 (140 Reviews)
Condo
Antigua Retreat- 2BR 2BA waterfront condo w/pool & boat slip
  • Air Conditioner
  • Parking
  • Pool

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Flamingo Retreat-waterfront 2BR 2BA condo w/pool & boat slip From US $852
         

9.2 (105 Reviews)
Condo
Flamingo Retreat-waterfront 2BR 2BA condo w/pool & boat slip
  • Air Conditioner
  • Parking
  • Pool

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Paradise Place by AvantStay | Key West Old Town Condo w/Shared Pool From US $736
         

9.2 (71 Reviews)
House
Paradise Place by AvantStay | Key West Old Town Condo w/Shared Pool
  • Air Conditioner
  • Pet Friendly
  • Pool

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About Meadows Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruisevacations Meadows, 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 Meadows. Places to stay near Meadows with prices averaging $506 a night.

Cruisevacations makes it easy and safe to find and compare vacation rentals in Meadows 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 Meadows

Type Count

Use these Quick Filters to Find a Vacation Rental in Meadows

★ Pro Tip: Cruisevacations makes it easy to compare the best listings on Cruisevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruisevacations 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 Meadows.

Weather in Meadows

View the weather forecast for Meadows before booking your Meadows 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

Other Places to Stay Near Meadows, FL


The Unitarian Universalist Fellowship of Key West 3,779 Properties The Meadows 117 Properties

Complexes around Meadows, FL


Bayfront Suites Marina 8 Properties Downtown Waterfront Dock 5 Properties Paradise Place 3 Properties Town Introductory Rates 3 Properties Casablanca 2 Properties