Fleming Key Pet Friendly Vacation Rentals
Apartment
10.0Exceptional
(98 Reviews)
1 Bedroom
1 Bath
2 Guests
300 ft²
Kitchen
Air Conditioner
Internet
Pet Friendly
US $314/Night
7 Nights - US $2,197
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(4 Reviews)
1 Bedroom
1 Bath
3 Guests
398.26 ft²
- Pet Friendly
Child Friendly
Security/Safety
US $364/Night
7 Nights - US $2,548
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
Parking
Pool
Balcony/Terrace- Internet
US $733/Night
7 Nights - US $5,131
Condo
10.0Exceptional
(76 Reviews)
1 Bedroom
1 Bath
4 Guests
731 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $535/Night
7 Nights - US $3,747
Apartment
10.0Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
6 Guests
645.83 ft²
- Parking
- Pool
View- Air Conditioner
US $1,339/Night
7 Nights - US $9,373
Condo
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(66 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
Oceanfront- Parking
Ocean View- Balcony/Terrace
US $514/Night
7 Nights - US $3,596
House
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
10.0Exceptional
(42 Reviews)
2 Bedrooms
3 Baths
8 Guests
1370 ft²
- Oceanfront
Hot Tub- Parking
- Ocean View
US $710/Night
7 Nights - US $4,968
House
- Key West
- ·
- Uptown - Upper Duval
- 0.09 mi to center
10.0Exceptional
(40 Reviews)
2 Bedrooms
2 Baths
4 Guests
1200 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $1,457/Night
7 Nights - US $10,202
Condo
10.0Exceptional
(37 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $649/Night
7 Nights - US $4,542
Pet-Friendly Vacation Rentals in Fleming Key
Over 1193+ Pet-Friendly Vacation Rentals in or Near Fleming Key
Condo
10.0Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
6 Guests
798 ft²
- Pool
- Kitchen
- Internet
- Pet Friendly
US $532/Night
7 Nights - US $3,724
House
- Key West
- ·
- Uptown - Upper Duval
- 0.10 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
785.77 ft²
- Pet Friendly
- Child Friendly
- Security/Safety
US $540/Night
7 Nights - US $3,778
Cottage
- Key West
- ·
- Uptown - Upper Duval
- 0.15 mi to center
9.8Exceptional
(7 Reviews)
1 Bedroom
1 Bath
- Ocean View
- Balcony/Terrace
- View
- Kitchen
US $646/Night
7 Nights - US $4,522
Cottage
10.0Exceptional
(33 Reviews)
2 Bedrooms
2 Baths
6 Guests
572 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $528/Night
7 Nights - US $3,696
House
- Key West
- ·
- Uptown - Upper Duval
- 0.12 mi to center
10.0Exceptional
(2 Reviews)
1 Bedroom
1 Bath
8 Guests
882.64 ft²
Breakfast- View
- Pet Friendly
- Child Friendly
US $535/Night
7 Nights - US $3,745
Apartment
10.0Exceptional
(28 Reviews)
1 Bedroom
1 Bath
2 Guests
475 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $145/Night
7 Nights - US $1,018
Condo
- Key West
- ·
- Truman Annex
- 0.21 mi to center
10.0Exceptional
(27 Reviews)
2 Bedrooms
1 Bath
4 Guests
680 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $292/Night
7 Nights - US $2,044
House
- Key West
- ·
- Key West Historic District
- 0.12 mi to center
10.0Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
1000 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $539/Night
7 Nights - US $3,770
House
10.0Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
4 Guests
1026 ft²
Private Pool- Pool
- Balcony/Terrace
- Kitchen
US $262/Night
7 Nights - US $1,832
Luxury Places to Stay in Fleming Key
Over 1184+ Luxury Places to Stay in or Near Fleming Key
House
- Key West
- ·
- Bahama Village
- 0.08 mi to center
4 Bedrooms
4 Baths
8 Guests
3175.35 ft²
- Parking
- Pool
Spa- Internet
Unlock the Best Price
House
8 Bedrooms
10 Baths
20 Guests
3702.79 ft²
- Parking
- Pool
- Spa
- Internet
US $5,694/Night
7 Nights - US $39,858
Apartment
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
10.0Exceptional
(1 Review)
8 Bedrooms
8 Baths
20 Guests
5000 ft²
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Internet
US $4,522/Night
7 Nights - US $31,652
House
5 Bedrooms
4 Baths
16 Guests
2098.96 ft²
- Parking
- Pool
- View
- Air Conditioner
US $4,328/Night
7 Nights - US $30,296
House
- Key West
- ·
- Historic Seaport
- 0.30 mi to center
10.0Exceptional
(8 Reviews)
7 Bedrooms
8 Baths
16 Guests
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $4,016/Night
7 Nights - US $28,111
Apartment
- Key West
- ·
- Historic Seaport
- 0.10 mi to center
7 Bedrooms
8 Baths
19 Guests
3110.77 ft²
- Parking
- Pool
- Balcony/Terrace
- View
US $3,990/Night
7 Nights - US $27,930
Apartment
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
1 Bedroom
8 Baths
20 Guests
5005.22 ft²
- Internet
- Pet Friendly
- Child Friendly
Laundry
US $3,894/Night
7 Nights - US $27,261
House
13 Bedrooms
15 Baths
32 Guests
5198.97 ft²
- Parking
- Pool
- Spa
- Internet
US $3,888/Night
7 Nights - US $27,216
New
House
6 Bedrooms
7 Baths
14 Guests
3500 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $3,707/Night
7 Nights - US $25,946
Top-Rated Vacation Rentals with a Pool in Fleming Key
Over 792+ Top-Rated Vacation Rentals with a Pool in or Near Fleming Key
House
10.0Exceptional
(144 Reviews)
5 Bedrooms
5 Baths
12 Guests
2651 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,474/Night
7 Nights - US $10,321
House
- Key West
- ·
- Key West Historic District
- 0.14 mi to center
10.0Exceptional
(143 Reviews)
3 Bedrooms
2 Baths
6 Guests
1415 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $2,321/Night
7 Nights - US $16,247
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(137 Reviews)
4 Bedrooms
4 Baths
8 Guests
1800 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,156/Night
7 Nights - US $8,090
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(102 Reviews)
6 Bedrooms
6 Baths
12 Guests
2644 ft²
- Private Pool
- Parking
- Pool
- Balcony/Terrace
US $1,529/Night
7 Nights - US $10,705
Condo
10.0Exceptional
(95 Reviews)
3 Bedrooms
3 Baths
8 Guests
2512 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,157/Night
7 Nights - US $8,101
House
- Key West
- ·
- Uptown - Upper Duval
- 0.06 mi to center
10.0Exceptional
(92 Reviews)
7 Bedrooms
7 Baths
16 Guests
2843 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,698/Night
7 Nights - US $11,884
House
10.0Exceptional
(92 Reviews)
3 Bedrooms
3 Baths
8 Guests
1541 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $795/Night
7 Nights - US $5,565
House
- Key West
- ·
- Key West Historic District
- 0.31 mi to center
10.0Exceptional
(88 Reviews)
3 Bedrooms
2 Baths
6 Guests
1860 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $861/Night
7 Nights - US $6,025
House
- Key West
- ·
- Bahama Village
- 0.09 mi to center
10.0Exceptional
(86 Reviews)
3 Bedrooms
3 Baths
6 Guests
1632 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $560/Night
7 Nights - US $3,922
Large Vacation Homes & Villas in Fleming Key
Over 181+ Large Vacation Homes & Villas in or Near Fleming Key
House
- Key West
- ·
- Uptown - Upper Duval
- 0.05 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
5 Baths
14 Guests
2571 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,527/Night
7 Nights - US $10,690
House
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
9.5Exceptional
(6 Reviews)
4 Bedrooms
4 Baths
10 Guests
2497.23 ft²
- Air Conditioner
- Internet
- Pet Friendly
Sports/Activities
US $1,964/Night
7 Nights - US $13,745
House
10.0Exceptional
(70 Reviews)
6 Bedrooms
6 Baths
16 Guests
2177 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $2,061/Night
7 Nights - US $14,428
Bed & Breakfast
- Key West
- ·
- Historic Seaport
- 0.16 mi to center
9.3Exceptional
(221 Reviews)
8 Bedrooms
6 Baths
12 Guests
318.61 ft²
- Oceanfront
- Hot Tub
- Breakfast
- Parking
US $254/Night
7 Nights - US $1,781
House
- Key West
- ·
- Uptown - Upper Duval
- 0.03 mi to center
10.0Exceptional
(59 Reviews)
4 Bedrooms
5 Baths
12 Guests
1576 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,122/Night
7 Nights - US $7,851
House
10.0Exceptional
(52 Reviews)
6 Bedrooms
7 Baths
16 Guests
3082 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $1,506/Night
7 Nights - US $10,544
House
10.0Exceptional
(36 Reviews)
5 Bedrooms
4 Baths
13 Guests
2116 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,116/Night
7 Nights - US $7,810
House
- Key West
- ·
- Historic Seaport
- 0.19 mi to center
10.0Exceptional
(33 Reviews)
6 Bedrooms
7 Baths
16 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,807/Night
7 Nights - US $12,647
Condo
- Key West
- ·
- Historic Seaport
- 0.28 mi to center
10.0Exceptional
(29 Reviews)
4 Bedrooms
4 Baths
12 Guests
2500 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $1,952/Night
7 Nights - US $13,661
Wheelchair Accessible Vacation Homes in Fleming Key
Over 156+ Wheelchair Accessible Vacation Homes in or Near Fleming Key
Condo
10.0Exceptional
(7 Reviews)
2 Bedrooms
2 Baths
4 Guests
1500 ft²
- Oceanfront
- Hot Tub
- Parking
- Pool
US $226/Night
7 Nights - US $1,579
Apartment
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Ocean View
- View
- Air Conditioner
US $276/Night
7 Nights - US $1,932
Hotel
8.6Fabulous
(2605 Reviews)
1 Bath
- Hot Tub
- Breakfast
- Parking
- Pool
US $192/Night
7 Nights - US $1,342
Condo
9.8Exceptional
(39 Reviews)
2 Bedrooms
2 Baths
6 Guests
1200 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $403/Night
7 Nights - US $2,823
House
- Key West
- ·
- Key West Historic District
- 0.13 mi to center
9.0Exceptional
(1147 Reviews)
18 Bedrooms
18 Baths
72 Guests
346.84 ft²
- Oceanfront
- Breakfast
EV Charge Station- Parking
US $738/Night
7 Nights - US $5,166
Condo
9.8Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
8 Guests
1350 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $703/Night
7 Nights - US $4,922
Condo
9.6Exceptional
(45 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $601/Night
7 Nights - US $4,207
Condo
9.6Exceptional
(29 Reviews)
2 Bedrooms
2 Baths
8 Guests
1300 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $506/Night
7 Nights - US $3,543
Condo
9.6Exceptional
(23 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Hot Tub
- Parking
- Pool
- Balcony/Terrace
US $324/Night
7 Nights - US $2,271
Fleming Key Petfriendly and Airbnb Homes Under $200
Over 81+ Fleming Key Petfriendly and Airbnb Homes Under $200
House
10.0Exceptional
(11 Reviews)
1 Bedroom
1 Bath
4 Guests
620 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $164/Night
7 Nights - US $1,147
House
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
2 Guests
710.42 ft²
- Parking
- Pool
- View
- Air Conditioner
US $190/Night
7 Nights - US $1,330
House
- Key West
- ·
- Key West Historic District
- 0.36 mi to center
10.0Exceptional
(10 Reviews)
2 Bedrooms
2 Baths
4 Guests
1140 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $183/Night
7 Nights - US $1,279
Hotel
8.3Excellent
(1373 Reviews)
4 Baths
350.9 ft²
- Hot Tub
- EV Charge Station
- Parking
- Pool
US $195/Night
7 Nights - US $1,362
Apartment
- Key West
- ·
- Key West Historic District
- 0.24 mi to center
10.0Exceptional
(6 Reviews)
1 Bedroom
1 Bath
2 Guests
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $111/Night
7 Nights - US $775
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
248 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $158/Night
7 Nights - US $1,109
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
550 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $137/Night
7 Nights - US $957
Apartment
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
6 Guests
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $121/Night
7 Nights - US $849
House
- Key West
- ·
- Uptown - Upper Duval
- 0.17 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
2 Baths
5 Guests
888 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $182/Night
7 Nights - US $1,272
Instantly Bookable Vacation Homes in Fleming Key
Over 737+ Instantly Bookable Vacation Homes in or Near Fleming Key
House
10.0Exceptional
(21 Reviews)
2 Bedrooms
3 Baths
6 Guests
1425 ft²
- Oceanfront
- Parking
- Pool
- Ocean View
US $228/Night
7 Nights - US $1,597
Apartment
- Key West
- ·
- Historic Seaport
- 0.10 mi to center
9.4Exceptional
(9 Reviews)
1 Bedroom
1 Bath
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $459/Night
7 Nights - US $3,211
House
- Key West
- ·
- Key West Historic District
- 0.10 mi to center
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
1018 ft²
- Oceanfront
- Pool
- Ocean View
- Balcony/Terrace
US $1,002/Night
7 Nights - US $7,015
House
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
850 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $664/Night
7 Nights - US $4,648
House
10.0Exceptional
(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
902 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $200/Night
7 Nights - US $1,403
House
10.0Exceptional
(11 Reviews)
2 Bedrooms
1 Bath
4 Guests
854 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $362/Night
7 Nights - US $2,534
House
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
900 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $226/Night
7 Nights - US $1,583
House
- Key West
- ·
- Key West Historic District
- 0.37 mi to center
10.0Exceptional
(8 Reviews)
2 Bedrooms
2 Baths
6 Guests
1100 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $216/Night
7 Nights - US $1,513
House
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
4 Guests
1283 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $437/Night
7 Nights - US $3,061
Book a Last Minute Place to Stay in Fleming Key
About Fleming Key Vacation Rentals
There are more than 4121 places to stay in Fleming Key and many that are available that welcome pets. These options include dog-friendly hotels, resorts, rentals as well as short-term private accommodations (i.e. RVs, Condos, Cabins, Chalets, etc.). The places can provide you with a great option on your next holiday. Compare many pet-friendly places to stay in Fleming Key.
Are you seeking a last-minute pets-allowed hotel deal, or are you wanting to find the best deals available for hotels, resorts, cottages, condos, private villas, chalets, or a large vacation homes? With PetFriendly Fleming Key, you can quickly compare different options to find the hottest deals with a single click. Looking for pet travel at a resort with an infinity pool, hot tub, is pet-friendly, or features a large master suite bedrooms or has a fireplace? You can find hotels, resorts, or other popular Airbnb-style properties in or near Fleming Key. Places to stay near Fleming Key are 736.95 ft² on average, with prices averaging US $740 a night.
PetFriendly makes it easy to find and compare hotels, resorts, and holiday rentals in Fleming Key with prices often listed at a 30-40% off the rack rate. Just enter your destination and secure your pet-friendly place to stay today.
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Top Dog Hotels, Pet-Friendly Vacation Rentals, and Places to Stay in Fleming Key
| Type | Count |
|---|---|
| Vacation Homes | 2102 |
| Holiday Apartments | 547 |
| Cottages | 106 |
| Villas | 28 |
Use these Quick Filters to Find a Vacation Rental in Fleming Key
★ Pro Tip: PetFriendly™ has the best results when it comes to finding places to stay that accept pets anywhere around the world. Travelers can find and compare over 10 million listings from all over the world. Use the intelligent Filter feature to compare homes, hotels, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, inns, resorts, and more. Enjoy Pet Travel without Hassle in Fleming Key.
Weather in Fleming Key, FL
View the weather forecast for Fleming Key before booking your hotel or rental.
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
Stay Near Fleming Key, FL
PetFriendly finds and compares Pet-Friendly hotels, rentals, and resort listings near many of Fleming Key's attractions.
Frequently Asked Questions About Fleming Key?
What are the top vacation rentals in Fleming Key?
Find the best options in or near Fleming Key for pet-friendly travel. If you are planning a trip or vacation in Fleming Key, consider a week or two at exciting pets-allowed hotels, resorts, or other suggested properties best known as Top Vacation Rentals and Places to Stay in Fleming Key:
- *CASA VICTORIA @ OLD TOWN* Home & Pool + Last Key White Glove Service.
- ~CHAVEZ HOUSE~ The private pool and lanai are a Key West dream come true!
- ~ GRAND MAISON ~ Spacious home on Duval St with pool and 4 ensuite bedrooms.
- ~ MAISONS de LUXE ~ 2 Stunning Homes w/Private Pool ON DUVAL.
- Half block to Duval @ Mango Hideaway -studio apt
- *MAYA’S SECRET TREASURE* Pool & Balcony + Last Key White Glove Service.
- *SOUTHERNMOST HOSPITALITY VII* 7BR & Pool + Last Key White Glove Service.
- *THE CONTENTED CRANE @ OLD TOWN* Home & Pool + Last Key White Glove Service.
- *CASA SERENDIPITY @ OLD TOWN* Home & Pool + Last Key White Glove Service.
- *BAHAMIAN BAMBOO @ THE ANNEX* Chic Home + Last Key White Glove Service
How many vacation rentals have private pools in Fleming Key?
We have found 328 accommodation options with private pools in or near Fleming Key, many of which accept and welcome pets. Top-rated hotels, resorts,and places to stay that have access to a swimming pool include:
- *LARGE PRIVATE HEATED POOL and PATIO*1/3 Mile from Beach
- Welcome to Parrot Dice! An Old Town tropical oasis with a private heated pool.
- Key Lime Pie by AvantStay | Ideal Location w/Splash Pool & Out Door Dining
- Private Paradise with Heated Waterfall Pool
Which vacation homes in Fleming Key are best for families?
Are you looking for a family-friendly and pet-friendly hotel, resort, or vacation home in Fleming Key? Check these highly-rated pet accommodations and places to stay with excellent reviews for families or groups staying in Fleming Key:
- Family House, 2 K BR`s, Private Spa/Deck, 2 pools.
- Egret Suite | Bright Retreat, Hot Tubs, Steps from Duval!
- New The Cottage at James House
How many PetFriendly vacation rentals are available in Fleming Key?
PetFriendly™ updates its properties regularly to bring you a great selection of places to stay with their pet policies clearly spelled out. At present, the total number of active properties listed by PetFriendly in 2026 is over 4121 in the Fleming Key area, and still growing every day. When we combine listings from multiple websites and travel providers, PetFriendly can provide you with a huge selection of the best places to stay that welcome pets in Fleming Key.
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