https://www.redweek.com/featured/spring-summer-rentals/North+America/United+States/Florida en Tue, 05 May 2026 18:34:13 -0700 3600 Verified & Protected

Marriott's Grande Vista

Orlando, Florida

• May 9–15, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $2,859 ($476/night)

]]> https://www.redweek.com/posting/R1408027 Fri, 26 Dec 2025 13:35:20 -0800 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• May 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,459 ($208/night)

]]> https://www.redweek.com/posting/R1365506 Wed, 12 Nov 2025 09:19:03 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• May 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,384 ($626/night)

]]> https://www.redweek.com/posting/R1317886 Sun, 03 Aug 2025 18:03:14 -0700

Disney's Old Key West Resort

Lake Buena Vista, Florida

• May 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 9
• $3,786 ($541/night)

]]> https://www.redweek.com/posting/R1439829 Sat, 28 Feb 2026 14:44:32 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 15–22, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,204 ($315/night)

]]> https://www.redweek.com/posting/R1397255 Thu, 18 Dec 2025 08:31:10 -0800 Verified & Protected

The Galleon Resort

Key West, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,513 ($502/night)

]]> https://www.redweek.com/posting/R1440630 Thu, 12 Mar 2026 08:39:11 -0700 Verified & Protected

Marriott's Sabal Palms

Orlando, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,423 ($346/night)

]]> https://www.redweek.com/posting/R1422058 Thu, 29 Jan 2026 12:23:53 -0800 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• May 16–22, 2026 (6 nights)
• 3 bed/2 bath, sleeps 10
• $3,076 ($513/night)

]]> https://www.redweek.com/posting/R1447518 Tue, 17 Mar 2026 07:12:20 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $777 ($111/night)

]]> https://www.redweek.com/posting/R1402829 Fri, 19 Dec 2025 10:03:12 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,314 ($331/night)

]]> https://www.redweek.com/posting/R1289240 Fri, 02 May 2025 13:46:42 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• May 16–26, 2026 (10 nights)
• 2 bed/2 bath, sleeps 8
• $5,475 ($548/night)

]]> https://www.redweek.com/posting/R1464401 Thu, 23 Apr 2026 09:11:39 -0700 Verified & Protected

Holiday Inn Club Vacations Marco Island - Sunset Cove Resort

Marco Island, Florida

• May 16–23, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $2,205 ($315/night)

]]> https://www.redweek.com/posting/R1337212 Tue, 11 Nov 2025 21:14:37 -0800 Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,330 ($190/night)

]]> https://www.redweek.com/posting/R1447945 Tue, 24 Mar 2026 14:13:35 -0700 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1390957 Wed, 19 Nov 2025 22:02:45 -0800 Verified & Protected

Hyatt Siesta Key Beach - A Hyatt Residence Club

Siesta Key, Florida

• May 16–23, 2026 (7 nights)
• 3 bed/3 bath, sleeps 6
• $4,603 ($658/night)

]]> https://www.redweek.com/posting/R1456508 Tue, 14 Apr 2026 08:44:30 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,165 ($166/night)

]]> https://www.redweek.com/posting/R1416468 Wed, 04 Feb 2026 10:08:08 -0800 Verified & Protected

The Charter Club of Marco Beach

Marco Island, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1422989 Tue, 10 Mar 2026 08:29:04 -0700 Verified & Protected

The Galleon Resort

Key West, Florida

• May 16–23, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,968 ($424/night)

]]> https://www.redweek.com/posting/R1444471 Thu, 12 Mar 2026 08:37:51 -0700

Hyatt Sunset Harbor Resort

Key West, Florida

• May 17–24, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $1,220 ($174/night)

]]> https://www.redweek.com/posting/R1458585 Wed, 08 Apr 2026 16:22:19 -0700 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• May 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,750 ($393/night)

]]> https://www.redweek.com/posting/R1390958 Wed, 19 Nov 2025 22:02:50 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• May 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,022 ($432/night)

]]> https://www.redweek.com/posting/R1430697 Mon, 16 Feb 2026 08:18:39 -0800 Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

• May 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $888 ($127/night)

]]> https://www.redweek.com/posting/R1445963 Fri, 27 Mar 2026 12:03:54 -0700 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• May 17–23, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $1,660 ($277/night)

]]> https://www.redweek.com/posting/R1433209 Mon, 09 Mar 2026 07:37:23 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• May 17–22, 2026 (5 nights)
• 3 bed/3 bath, sleeps 10
• $1,660 ($332/night)

]]> https://www.redweek.com/posting/R1448394 Sat, 21 Mar 2026 08:56:48 -0700 Verified & Protected

The Cabins at Disney's Fort Wilderness Resort

Lake Buena Vista, Florida

• May 17–18, 2026 (1 night)
• 1 bed/1 bath, sleeps 6
• $541 ($541/night)

]]> https://www.redweek.com/posting/R1435467 Wed, 18 Feb 2026 14:09:45 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• May 17–22, 2026 (5 nights)
• 3 bed/3 bath, sleeps 10
• $4,166 ($833/night)

]]> https://www.redweek.com/posting/R1433688 Sun, 15 Feb 2026 12:27:00 -0800 Verified & Protected

Westgate Town Center

Kissimmee, Florida

• May 17–24, 2026 (7 nights)
• 4 bed/4 bath, sleeps 16
• $2,257 ($322/night)

]]> https://www.redweek.com/posting/R1368183 Fri, 14 Nov 2025 14:31:12 -0800 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• May 17–24, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,330 ($190/night)

]]> https://www.redweek.com/posting/R1439236 Fri, 27 Feb 2026 15:33:04 -0800 Verified & Protected

Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

• May 18–21, 2026 (3 nights)
• 1 bed/2 bath, sleeps 5
• $2,641 ($880/night)

]]> https://www.redweek.com/posting/R1455292 Wed, 08 Apr 2026 06:39:32 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• May 18–23, 2026 (5 nights)
• 3 bed/3 bath, sleeps 10
• $3,621 ($724/night)

]]> https://www.redweek.com/posting/R1436949 Sat, 21 Feb 2026 16:24:28 -0800 Verified & Protected

Hyatt Beach House Resort

Key West, Florida

• May 19–22, 2026 (3 nights)
• 2 bed/2 bath, sleeps 6
• $777 ($259/night)

]]> https://www.redweek.com/posting/R1450512 Tue, 24 Mar 2026 14:58:29 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• May 21–23, 2026 (2 nights)
• 1 bed/1 bath, sleeps 4
• $455 ($228/night)

]]> https://www.redweek.com/posting/R1450531 Mon, 30 Mar 2026 14:38:12 -0700 Verified & Protected

Disney's Old Key West Resort

Lake Buena Vista, Florida

• May 21–26, 2026 (5 nights)
• 2 bed/2 bath, sleeps 9
• $2,478 ($496/night)

]]> https://www.redweek.com/posting/R1466568 Thu, 30 Apr 2026 04:25:23 -0700 Verified & Protected

Wyndham Beach Street Cottages

Destin, Florida

• May 21–24, 2026 (3 nights)
• 1 bed/1 bath, sleeps 6
• $705 ($235/night)

]]> https://www.redweek.com/posting/R1454873 Tue, 31 Mar 2026 14:44:35 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• May 22–25, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $666 ($222/night)

]]> https://www.redweek.com/posting/R1449515 Thu, 02 Apr 2026 08:06:04 -0700 Verified & Protected

Marriott's Oceana Palms

Riviera Beach, Florida

• May 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,257 ($751/night)

]]> https://www.redweek.com/posting/R1459622 Thu, 16 Apr 2026 13:53:31 -0700 Verified & Protected

Marriott's Villas at Doral

Miami, Florida

• May 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $2,474 ($353/night)

]]> https://www.redweek.com/posting/R1416863 Tue, 13 Jan 2026 11:44:42 -0800 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

• May 22–29, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $665 ($95/night)

]]> https://www.redweek.com/posting/R1348912 Tue, 11 Nov 2025 21:14:37 -0800 Verified & Protected

Marriott's Harbour Lake

Orlando, Florida

• May 22–26, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $1,110 ($278/night)

]]> https://www.redweek.com/posting/R1454125 Tue, 31 Mar 2026 07:17:37 -0700 Verified & Protected

Grande Villas Resort

Orlando, Florida

• May 22–29, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $888 ($127/night)

]]> https://www.redweek.com/posting/R1416983 Thu, 05 Feb 2026 10:24:16 -0800 Verified & Protected

Club Wyndham Clearwater Beach Resort

Clearwater, Florida

• May 22–26, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $3,295 ($824/night)

]]> https://www.redweek.com/posting/R1443965 Thu, 26 Mar 2026 08:01:07 -0700 Verified & Protected

Eagle's Nest Beach Resort

Marco Island, Florida

• May 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,298 ($471/night)

]]> https://www.redweek.com/posting/R1446801 Thu, 19 Mar 2026 12:09:05 -0700 Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

• May 22–29, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $973 ($139/night)

]]> https://www.redweek.com/posting/R1448975 Tue, 24 Mar 2026 08:36:58 -0700 Verified & Protected

Marriott's Villas at Doral

Miami, Florida

• May 22–26, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $2,368 ($592/night)

]]> https://www.redweek.com/posting/R1432422 Fri, 13 Feb 2026 15:53:09 -0800

Disney's Old Key West Resort

Lake Buena Vista, Florida

• May 22–29, 2026 (7 nights)
• 1 bed/1 bath, sleeps 5
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1464423 Wed, 22 Apr 2026 21:26:03 -0700 Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

• May 22–26, 2026 (4 nights)
• 3 bed/3 bath, sleeps 12
• $777 ($194/night)

]]> https://www.redweek.com/posting/R1411017 Wed, 14 Jan 2026 15:40:09 -0800

Sheraton Vistana Resort

Orlando, Florida

• May 22–29, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,440 ($206/night)

]]> https://www.redweek.com/posting/R1434999 Tue, 17 Feb 2026 16:22:59 -0800

Disney's Old Key West Resort

Lake Buena Vista, Florida

• May 22–29, 2026 (7 nights)
• 1 bed/1 bath, sleeps 5
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1467000 Wed, 29 Apr 2026 13:29:28 -0700